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Literature summary for 2.7.11.2 extracted from

  • Meng, T.; Zhang, D.; Xie, Z.; Yu, T.; Wu, S.; Wyder, L.; Regenass, U.; Hilpert, K.; Huang, M.; Geng, M.; Shen, J.
    Discovery and optimization of 4,5-diarylisoxazoles as potent dual inhibitors of pyruvate dehydrogenase kinase and heat shock protein 90 (2014), J. Med. Chem., 57, 9832-9843.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(4-benzylpiperidin-1-yl)[5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-1,2-oxazol-3-yl]methanone
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(2-methoxyphenyl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(3,4-dichlorophenyl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(3-methoxyphenyl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(4-methoxyphenyl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(pyridin-2-yl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(pyrimidin-2-yl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(2-methoxyphenyl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(3,4-dichlorophenyl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(3-methoxyphenyl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(4-methoxyphenyl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(pyridin-2-yl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(pyrimidin-2-yl)piperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
(E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-phenylpiperazin-1-yl)prop-2-en-1-one
-
Homo sapiens
4-[[5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-1,2-oxazole-3-carbonyl]amino]-N-ethylpiperidine-1-carboxamide
-
Homo sapiens
5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-N-(pyridin-4-yl)-1,2-oxazole-3-carboxamide
-
Homo sapiens
5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-N-[1-(2-methylpropyl)piperidin-4-yl]-1,2-oxazole-3-carboxamide
-
Homo sapiens
5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-N-[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]-1,2-oxazole-3-carboxamide
-
Homo sapiens
5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-N-[1-[(pyridin-4-yl)methyl]piperidin-4-yl]-1,2-oxazole-3-carboxamide
-
Homo sapiens
5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
-
Homo sapiens
5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-[4-[(morpholin-4-yl)methyl]phenyl]-1,2-oxazole-3-carboxamide
-
Homo sapiens
5-(5-chloro-2,4-dihydroxyphenyl)-N-[(2,4-dichlorophenyl)methyl]-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
-
Homo sapiens
5-(5-chloro-2,4-dihydroxyphenyl)-N-[1-(cyclopropylmethyl)piperidin-4-yl]-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
-
Homo sapiens
5-(5-chloro-2,4-dihydroxyphenyl)-N-[1-[(2,4-dichlorophenyl)methyl]piperidin-4-yl]-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
-
Homo sapiens
5-(5-chloro-2,4-dihydroxyphenyl)-N-[4-(dimethylamino)phenyl]-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
-
Homo sapiens
AUY922
-
Homo sapiens
AZD7545
-
Homo sapiens
Dichloroacetate
-
Homo sapiens
M77976
-
Homo sapiens
methyl 4-[[5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-1,2-oxazole-3-carbonyl]amino]piperidine-1-sulfinate
-
Homo sapiens
N-(1-acetylpiperidin-4-yl)-5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
-
Homo sapiens
N-(1-benzylpiperidin-4-yl)-5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
-
Homo sapiens
Nov3r
-
Homo sapiens
radicicol
-
Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
ATP + [pyruvate dehydrogenase A1 (acetyl-transferring)] Homo sapiens
-
ADP + [pyruvate dehydrogenase A1 (acetyl-transferring)] phosphate
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens Q15118
-
-

Purification (Commentary)

Purification (Comment) Organism
nickel column chromatography Homo sapiens

Source Tissue

Source Tissue Comment Organism Textmining
A-549 cell
-
Homo sapiens
-
H-460 cell
-
Homo sapiens
-
HCT-116 cell
-
Homo sapiens
-
MDA-MB-231 cell
-
Homo sapiens
-
NCI-H1299 cell
-
Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
ATP + [pyruvate dehydrogenase A1 (acetyl-transferring)]
-
Homo sapiens ADP + [pyruvate dehydrogenase A1 (acetyl-transferring)] phosphate
-
?

Synonyms

Synonyms Comment Organism
PDHK1
-
Homo sapiens
pyruvate dehydrogenase kinase
-
Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000017
-
pH and temperature not specified in the publication Homo sapiens 5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-N-[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]-1,2-oxazole-3-carboxamide
0.000025
-
pH and temperature not specified in the publication Homo sapiens N-(1-benzylpiperidin-4-yl)-5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
0.000028
-
pH and temperature not specified in the publication Homo sapiens 5-(5-chloro-2,4-dihydroxyphenyl)-N-[1-(cyclopropylmethyl)piperidin-4-yl]-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
0.000059
-
pH and temperature not specified in the publication Homo sapiens 5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-N-[1-[(pyridin-4-yl)methyl]piperidin-4-yl]-1,2-oxazole-3-carboxamide
0.000068
-
pH and temperature not specified in the publication Homo sapiens 5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-N-[1-(2-methylpropyl)piperidin-4-yl]-1,2-oxazole-3-carboxamide
0.00013
-
pH and temperature not specified in the publication Homo sapiens methyl 4-[[5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-1,2-oxazole-3-carbonyl]amino]piperidine-1-sulfinate
0.00015
-
pH and temperature not specified in the publication Homo sapiens 4-[[5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-1,2-oxazole-3-carbonyl]amino]-N-ethylpiperidine-1-carboxamide
0.00016
-
pH and temperature not specified in the publication Homo sapiens 5-(5-chloro-2,4-dihydroxyphenyl)-N-[1-[(2,4-dichlorophenyl)methyl]piperidin-4-yl]-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
0.00021
-
pH and temperature not specified in the publication Homo sapiens N-(1-acetylpiperidin-4-yl)-5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
0.00038
-
pH and temperature not specified in the publication Homo sapiens 5-(5-chloro-2,4-dihydroxyphenyl)-N-[4-(dimethylamino)phenyl]-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
0.000491
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(3-methoxyphenyl)piperazin-1-yl)prop-2-en-1-one
0.000521
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(pyrimidin-2-yl)piperazin-1-yl)prop-2-en-1-one
0.000557
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(4-methoxyphenyl)piperazin-1-yl)prop-2-en-1-one
0.00058
-
pH and temperature not specified in the publication Homo sapiens 5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-N-(pyridin-4-yl)-1,2-oxazole-3-carboxamide
0.000604
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(2-methoxyphenyl)piperazin-1-yl)prop-2-en-1-one
0.00061
-
pH and temperature not specified in the publication Homo sapiens 5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
0.00061
-
pH and temperature not specified in the publication Homo sapiens 5-(5-chloro-2,4-dihydroxyphenyl)-N-[(2,4-dichlorophenyl)methyl]-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
0.000776
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(3-methoxyphenyl)piperazin-1-yl)prop-2-en-1-one
0.000845
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(2-methoxyphenyl)piperazin-1-yl)prop-2-en-1-one
0.000878
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(pyridin-2-yl)piperazin-1-yl)prop-2-en-1-one
0.00095
-
pH and temperature not specified in the publication Homo sapiens 5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-[4-[(morpholin-4-yl)methyl]phenyl]-1,2-oxazole-3-carboxamide
0.000952
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(4-methoxyphenyl)piperazin-1-yl)prop-2-en-1-one
0.00105
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(pyridin-2-yl)piperazin-1-yl)prop-2-en-1-one
0.00107
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(pyrimidin-2-yl)piperazin-1-yl)prop-2-en-1-one
0.001417
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(3,4-dichlorophenyl)piperazin-1-yl)prop-2-en-1-one
0.001916
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-phenylpiperazin-1-yl)prop-2-en-1-one
0.002369
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)prop-2-en-1-one
0.002949
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-isoxazol-3-yl)-1-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)prop-2-en-1-one
0.004306
-
pH and temperature not specified in the publication Homo sapiens (E)-3-(5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-isoxazol-3-yl)-1-(4-(3,4-dichlorophenyl)piperazin-1-yl)prop-2-en-1-one
0.01
-
IC50 above 0.01 mM, pH and temperature not specified in the publication Homo sapiens (4-benzylpiperidin-1-yl)[5-(5-chloro-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-1,2-oxazol-3-yl]methanone
0.0113
-
pH and temperature not specified in the publication Homo sapiens AUY922