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(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
2-amino-N-hydroxy-3-(1-H-indol-3-yl)-propionimidic acid
highest affinity of all the ligands examined, due to Zn2+-hydroxamate coordination, KD value of 0.0019 mM
4-amino-1-(3-O-phosphono-a-D-lyxofuranosyl)pyrimidin-2(1H)-one
-
4-amino-1-[(2S,3aS,4S,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxidotetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-4-yl]pyrimidin-2(1H)-one
KD value of 20.5 mM
4-amino-1-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]pyrimidin-2(1H)-one
KD value of 0.925 mM
5-fluorocytidine
KD value of 2.02 mM
Cidofovir
KD value of ca. 40 mM
Cytosine arabinoside monophosphate
KD value of 18.91 mM
EDTA
5 mM. Activity can be restored by the addition of Mg2+ to a concentration of 10 mM
N-([4-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-1-naphthyl]methyl)-4-chlorobenzamide
1 mM, 52% inhibition
N-([4-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-1-naphthyl]methyl)benzamide
1 mM, 59% inhibition
N-[4-[(6-aminopyridin-3-yl)amino]-3-methylbenzyl]-4-(trifluoromethyl)benzamide
1 mM, 60% inhibition
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
-
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
-
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
-
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
-
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
-
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
additional information
5-(1,3-benzodioxol-5-ylamino)-5-oxopentanoic acid, 2-[(2,6-diaminopyrimidin-4-yl)sulfanyl]acetamide and 4-(5-amino-1,3,4-oxadiazol-2-yl)-1,2,5-oxadiazol-3-amine are inactive. Activity with compounds 2-amino-N-hydroxy-acetimidic acid, N-hydroxy-nicotinimidic acid, 5-bromo-thiophene-2-sulfonic acid amide, 4-bromobenzenesulfonamide and 4-(4-dimethylamino-phenylazo)-benzenesulfonamide are not measurable
-
additional information
-
5-(1,3-benzodioxol-5-ylamino)-5-oxopentanoic acid, 2-[(2,6-diaminopyrimidin-4-yl)sulfanyl]acetamide and 4-(5-amino-1,3,4-oxadiazol-2-yl)-1,2,5-oxadiazol-3-amine are inactive. Activity with compounds 2-amino-N-hydroxy-acetimidic acid, N-hydroxy-nicotinimidic acid, 5-bromo-thiophene-2-sulfonic acid amide, 4-bromobenzenesulfonamide and 4-(4-dimethylamino-phenylazo)-benzenesulfonamide are not measurable
-
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0.0089 - 0.06
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.02 - 0.192
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
0.018 - 0.223
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
0.002 - 0.069
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0176 - 0.3
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
0.0015 - 0.018
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0015 - 0.032
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.089 - 0.322
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0016 - 0.212
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0032 - 0.3
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0028 - 0.3
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.3
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
0.0039 - 0.058
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0019 - 0.036
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0063 - 0.3
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
0.015 - 0.039
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.000007
artesunate
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.000013
Chloroquine
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.54
N-([4-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-1-naphthyl]methyl)-4-chlorobenzamide
Escherichia coli
-
0.45
N-([4-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-1-naphthyl]methyl)benzamide
Escherichia coli
-
0.49
N-[4-[(6-aminopyridin-3-yl)amino]-3-methylbenzyl]-4-(trifluoromethyl)benzamide
Escherichia coli
-
0.0089
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.014
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.032
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.06
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.02
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.056
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.065
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.069
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.192
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.018
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.077
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.087
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.141
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.223
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.002
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.0021
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.012
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.035
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.069
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.0176
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.3
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.0015
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.0032
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.0051
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.011
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.018
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.0015
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.0061
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.0068
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.0096
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.032
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.089
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.102
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.322
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.0016
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.125
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.13
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.208
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.212
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.0032
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.3
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.0028
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.3
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.0039
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.0079
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.013
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.032
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.058
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.0019
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.0074
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.0079
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.018
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.036
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.0063
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.3
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.3
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.015
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.018
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.022
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.039
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
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Takagi, M.; Kuzuyama, T.; Kaneda, K.; Watanabe, H.; Dairi, T.; Seto, H.
Studies on the nonmevalonate pathway: Formation of 2-C-methyl-D-erythritol 2,4-cyclodiphosphate from 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
Tetrahedron Lett.
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3395-3398
2000
Escherichia coli, Escherichia coli (P62617)
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brenda
Kishida, H.; Wada, T.; Unzai, S.; Kuzuyama, T.; Takagi, M.; Terada, T.; Shirouzu, M.; Yokoyama, S.; Tame, J.R.; Park, S.Y.
Structure and catalytic mechanism of 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (MECDP) synthase, an enzyme in the non-mevalonate pathway of isoprenoid synthesis
Acta Crystallogr. Sect. D
59
23-31
2003
Thermus thermophilus (Q8RQP5)
brenda
Ni, S.; Robinson, H.; Marsing, G.C.; Bussiere, D.E.; Kennedy, M.A.
Structure of 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase from Shewanella oneidensis at 1.6 ANG: identification of farnesyl pyrophosphate trapped in a hydrophobic cavity
Acta Crystallogr. Sect. D
D60
1949-1957
2004
Shewanella oneidensis, Shewanella oneidensis MR1
brenda
Rohdich, F.; Eisenreich, W.; Wungsintaweekul, J.; Hecht, S.; Schuhr, C.A.; Bacher, A.
Biosynthesis of terpenoids. 2C-methyl-D-erythritol 2,4-cyclodiphosphate synthase (ispF) from Plasmodium falciparum
Eur. J. Biochem.
268
3190-3197
2001
Plasmodium falciparum (P62368), Plasmodium falciparum
brenda
Campbell, T.L.; Brown, E.D.
Characterization of the depletion of 2-C-methyl-D-erythritol-2,4-cyclodiphosphate synthase in Escherichia coli and Bacillus subtilis
J. Bacteriol.
184
5609-5618
2002
Escherichia coli
brenda
Richard, S.B.; Ferrer, J.L.; Bowman, M.E.; Lillo, A.M.; Tetzlaff, C.N.; Cane, D.E.; Noel, J.P.
Structure and mechanism of 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase. An enzyme in the mevalonate-independent isoprenoid biosynthetic pathway
J. Biol. Chem.
277
8667-8672
2002
Escherichia coli (P62617)
brenda
Gabrielsen, M.; Bond, C.S.; Hallyburton, I.; Hecht, S.; Bacher, A.; Eisenreich, W.; Rohdich, F.; Hunter, W.N.
Hexameric assembly of the bifunctional methylerythritol 2,4-cyclodiphosphate synthase and protein-protein associations in the deoxy-xylulose-dependent pathway of isoprenoid precursor biosynthesis
J. Biol. Chem.
279
52753-52761
2004
Agrobacterium tumefaciens, Campylobacter jejuni, Escherichia coli (P62617), Escherichia coli
brenda
Steinbacher, S.; Kaiser, J.; Wungsintaweekul, J.; Hecht, S.; Eisenreich, W.; Gerhardt, S.; Bacher, A.; Rohdich, F.
Structure of 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase involved in mevalonate-independent biosynthesis of isoprenoids
J. Mol. Biol.
316
79-88
2002
Escherichia coli
brenda
Herz, S.; Wungsintaweekul, J.; Schuhr, C.A.; Hecht, S.; Lttgen, H.; Sagner, S.; Fellermeier, M.; Eisenreich, W.; Zenk, M.H.; Bacher, A.; Rohdich, F.
Biosynthesis of terpenoids: YgbB protein converts 4-diphosphocytidyl-2C-methyl-D-erythritol 2-phosphate to 2C-methyl-D-erythritol 2,4-cyclodiphosphate
Proc. Natl. Acad. Sci. USA
97
2486-2490
2000
Escherichia coli (P62617), Escherichia coli
brenda
Kemp, L.E.; Bond, C.S.; Hunter, W.N.
Structure of 2C-methyl-D-erythritol 2,4-cyclodiphosphate synthase: an essential enzyme for isoprenoid biosynthesis and target for antimicrobial drug development
Proc. Natl. Acad. Sci. USA
99
6591-6596
2002
Escherichia coli (P62617), Escherichia coli
brenda
Lehmann, C.; Lim, K.; Toedt, J.; Krajewski, W.; Howard, A.; Eisenstein, E.; Herzberg, O.
Structure of 2C-methyl-D-erythrol-2,4-cyclodiphosphate synthase from Haemophilus influenzae: Activation by conformational transition
Proteins
49
135-138
2002
Haemophilus influenzae (P44815), Haemophilus influenzae
brenda
Sgraja, T.; Kemp, L.E.; Ramsden, N.; Hunter, W.N.
A double mutation of Escherichia coli 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase disrupts six hydrogen bonds with, yet fails to prevent binding of, an isoprenoid diphosphate
Acta Crystallogr. Sect. F
F61
625-629
2005
Escherichia coli
brenda
Kim, S.M.; Kuzuyama, T.
Cloning and characterization of 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase (MECS) gene from Ginkgo biloba
Plant Cell Rep.
8
829-835
2006
Ginkgo biloba (Q1EDG4)
-
brenda
Lherbet, C.; Pojer, F.; Richard, S.B.; Noel, J.P.; Poulter, C.D.
Absence of substrate channeling between active sites in the Agrobacterium tumefaciens IspDF and IspE enzymes of the methyl erythritol phosphate pathway
Biochemistry
45
3548-3553
2006
Agrobacterium tumefaciens
brenda
Illarionova, V.; Kaiser, J.; Ostrozhenkova, E.; Bacher, A.; Fischer, M.; Eisenreich, W.; Rohdich, F.
Nonmevalonate terpene biosynthesis enzymes as antiinfective drug targets: substrate synthesis and high-throughput screening methods
J. Org. Chem.
71
8824-8834
2006
Plasmodium sp.
brenda
Baumgartner, C.; Eberle, C.; Diederich, F.; Lauw, S.; Rohdich, F.; Eisenreich, W.; Bacher, A.
Structure-based design and synthesis of the first weak non-phosphate inhibitors for IspF, an enzyme in the non-mevalonate pathway of isoprenoid biosynthesis
Helv. Chim. Acta
90
1043-1068
2007
Escherichia coli (P62617)
-
brenda
Jin, H.; Gong, Y.; Guo, B.; Qiu, C.; Liu, D.; Miao, Z.; Sun, X.; Tang, K.
Isolation and characterization of a 2C-methyl-D-erythritol 2,4-cyclodiphosphate synthase gene from Taxus media
Mol. Biol.
40
914-921
2006
Taxus x media (A1X5Y0)
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brenda
Hsieh, M.; Goodman, H.M.
Functional evidence for the involvement of Arabidopsis IspF homolog in the nonmevalonate pathway of plastid isoprenoid biosynthesis
Planta
223
779-784
2006
Arabidopsis thaliana
brenda
Calisto, B.M.; Perez-Gil, J.; Bergua, M.; Querol-Audi, J.; Fita, I.; Imperial, S.
Biosynthesis of isoprenoids in plants: Structure of the 2C-methyl-D-erythritol 2,4-cyclodiphosphate synthase from Arabidopsis thaliana. Comparison with the bacterial enzymes
Protein Sci.
16
2082-2088
2007
Arabidopsis thaliana (Q9CAK8), Arabidopsis thaliana
brenda
Sando, T.; Takeno, S.; Watanabe, N.; Okumoto, H.; Kuzuyama, T.; Yamashita, A.; Hattori, M.; Ogasawara, N.; Fukusaki, E.; Kobayashi, A.
Cloning and characterization of the 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway genes of a natural-rubber producing plant, Hevea brasiliensis
Biosci. Biotechnol. Biochem.
72
2903-2917
2008
Hevea brasiliensis (A9ZN12), Hevea brasiliensis
brenda
Chen, J.; Xiao, Y.; Di, P.; Yu, X.; Chen, W.; Zhang, L.
Molecular cloning and characterization of a 2C-methyl-D: -erythritol 2,4-cyclodiphosphate synthase gene from Cephalotaxus harringtonia
Mol. Biol. Rep.
36
1749-1756
2008
Cephalotaxus harringtonia
brenda
Narayanasamy, P.; Eoh, H.; Crick, D.C.
Chemoenzymatic synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol: a substrate for IspE
Tetrahedron Lett.
49
4461-4463
2008
Mycobacterium tuberculosis, Mycobacterium tuberculosis Rv3582c
brenda
Battilana, J.; Costantini, L.; Emanuelli, F.; Sevini, F.; Segala, C.; Moser, S.; Velasco, R.; Versini, G.; Stella Grando, M.
The 1-deoxy-D: -xylulose 5-phosphate synthase gene co-localizes with a major QTL affecting monoterpene content in grapevine
Theor. Appl. Genet.
118
653-669
2009
Vitis vinifera x Vitis vinifera, Vitis vinifera x Vitis riparia
brenda
Geist, J.G.; Lauw, S.; Illarionova, V.; Illarionov, B.; Fischer, M.; Graewert, T.; Rohdich, F.; Eisenreich, W.; Kaiser, J.; Groll, M.; Scheurer, C.; Wittlin, S.; Alonso-Gomez, J.L.; Schweizer, W.B.; Bacher, A.; Diederich, F.
Thiazolopyrimidine inhibitors of 2-methylerythritol 2,4-cyclodiphosphate synthase (IspF) from Mycobacterium tuberculosis and Plasmodium falciparum
ChemMedChem
5
1092-1101
2010
Arabidopsis thaliana (Q9CAK8), Arabidopsis thaliana, Escherichia coli, Mycobacterium tuberculosis (P9WKG5), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (P9WKG5), Plasmodium falciparum (P62369), Plasmodium falciparum, Plasmodium falciparum NF54 (P62369)
brenda
Ramsden, N.L.; Buetow, L.; Dawson, A.; Kemp, L.A.; Ulaganathan, V.; Brenk, R.; Klebe, G.; Hunter, W.N.
A structure-based approach to ligand discovery for 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase: a target for antimicrobial therapy
J. Med. Chem.
52
2531-2542
2009
Escherichia coli (P62617), Escherichia coli
brenda
Liu, W.; Chen, M.; Yang, C.; Yang, Y.; Lan, X.; Liao, Z.
A new 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase gene from Taxus media: Cloning, characterization and functional complementation
J. Med. Plant Res.
3
395-402
2009
Taxus x media (D3G6G3)
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brenda
Narayanasamy, P.; Eoh, H.; Brennan, P.J.; Crick, D.C.
Synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate and kinetic studies of Mycobacterium tuberculosis IspF, a potential drug target
Chem. Biol.
17
117-122
2010
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
brenda
Jung, Y.; Choi, J.; Sun, J.; Nou, I.; Cho, Y.; Kang, K.
Molecular and functional characterization of a Brmecp gene encoding 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase from Brassica rapa
J. Plant Biotechnol.
39
189-195
2012
Brassica rapa
-
brenda
Kumar, H.; Singh, K.; Kumar, S.
2C-Methyl-D-erythritol 2,4-cyclodiphosphate synthase from Stevia rebaudiana Bertoni is a functional gene
Mol. Biol. Rep.
39
10971-10978
2012
Stevia rebaudiana (Q0Q5B3), Stevia rebaudiana
brenda
Zheng, Y.; Chen, M.; Yang, C.; Ming, X.; Liu, X.; Lan, X.; Liao, Z.
Cloning and characterization of MECS and HDS genes from Rauvolfia verticillata
Plant OMICS
4
82-90
2011
Rauvolfia verticillata
-
brenda
Liu, Z.; Jin, Y.; Tao, Y.; Wang, G.
Crystal structure of IspF from Bacillus subtilis and absence of protein complex assembly amongst IspD/IspE/IspF enzymes in the MEP pathway
Biosci. Rep.
38
BSR20171370
2018
Bacillus subtilis (Q06756), Bacillus subtilis 168 (Q06756)
brenda
Mandal, S.; Upadhyay, S.; Singh, V.P.; Kapoor, R.
Enhanced production of steviol glycosides in mycorrhizal plants a concerted effect of arbuscular mycorrhizal symbiosis on transcription of biosynthetic genes
Plant Physiol. Biochem.
89
100-106
2015
Stevia rebaudiana
brenda