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Literature summary for 3.1.26.13 extracted from

  • Corona, A.; Desantis, J.; Massari, S.; Distinto, S.; Masaoka, T.; Sabatini, S.; Esposito, F.; Manfroni, G.; Maccioni, E.; Cecchetti, V.; Pannecouque, C.; Le Grice, S.; Tramontano, E.; Tabarrini, O.
    Studies on cycloheptathiophene-3-carboxamide derivatives as allosteric HIV-1 ribonuclease H inhibitors (2016), ChemMedChem, 11, 1709-1720 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 3.1.26.13

Cloned(Commentary)

Cloned (Comment) Organism
recombinant expression of His-tagged enzyme in Escherichia coli strain M15 Human immunodeficiency virus type 1 group M subtype B

Inhibitors

Inhibitors Comment Organism Structure
2,6-dimethoxy-N-(3-(pyridin-2-ylcarbamoyl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-2-yl)nicotinamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(2,4-dichlorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(2-(2-fluorophenyl)acetamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(2-aminobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(2-bromobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(2-chloro-4-fluorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(2-chlorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(2-cyclohexylacetamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(2-fluorobenzamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(2-fluorobenzamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid
-
 Human immunodeficiency virus type 1 group M subtype B
2-(2-fluorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(2-methoxybenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(2-methylbenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(2-nitrobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(3,4-dihydroxybenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(3,4-dihydroxyphenyl)-3,5,6,7,8,9-hexahydro-4H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-one
-
 Human immunodeficiency virus type 1 group M subtype B
2-(3,4-dimethoxybenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(3-fluorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(3-phenylpropanamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(4-aminobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(4-chlorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(4-fluorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-(4-nitrobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-acetamido-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-amino-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-benzamido-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-hydroxy-6-methoxy-N-(3-(pyridin-2-ylcarbamoyl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-2-yl)nicotinamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-[(cyclohexanecarbonyl)amino]-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-[3-(4-chlorophenyl)propanamido]-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
2-[3-(4-fluorophenyl)propanamido]-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
5,6-dimethyl-2-(4-nitrophenyl)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Human immunodeficiency virus type 1 group M subtype B
ethyl 2-(2-fluorobenzamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate
-
 Human immunodeficiency virus type 1 group M subtype B
ethyl 2-(4-chlorobenzamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate
-
 Human immunodeficiency virus type 1 group M subtype B
additional information inhibitor library screening, identification and synthesis of cycloheptathiophene-3-carboxamide derivatives as allosteric HIV-1 ribonuclease H inhibitors, binding mode of compounds 2-(3,4-dihydroxyphenyl)-3,5,6,7,8,9-hexahydro-4H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-one, 2-(3,4-dimethoxybenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide, and 2-(3,4-dihydroxybenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide, overview Human immunodeficiency virus type 1 group M subtype B
N-(3-((2-fluorophenyl)carbamoyl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-2-yl)picolinamide
-
 Human immunodeficiency virus type 1 group M subtype B
N-(pyridin-2-yl)-2-(thiophene-2-carboxamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
N-(pyridin-2-yl)-2-[2-(quinolin-6-yl)acetamido]-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
-
 Human immunodeficiency virus type 1 group M subtype B
NSC727447
-
 Human immunodeficiency virus type 1 group M subtype B

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ required Human immunodeficiency virus type 1 group M subtype B

Organism

Organism UniProt Comment Textmining
Human immunodeficiency virus type 1 group M subtype B P03366 HIV-1
-
Human immunodeficiency virus type 1 group M subtype B BH10 P03366 HIV-1
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged enzyme from Escherichia coli strain M15 by nickel and heparin affinity chromatography Human immunodeficiency virus type 1 group M subtype B

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information hybrid RNA/DNA 5'-GAUCUGAGCCUGGGAGCU-fluorescin-3' and 5'-dabsyl-AGCTCCCAGGCTCAGATC-3' are used for RNase H activity assays Human immunodeficiency virus type 1 group M subtype B ?
-
 ?
additional information hybrid RNA/DNA 5'-GAUCUGAGCCUGGGAGCU-fluorescin-3' and 5'-dabsyl-AGCTCCCAGGCTCAGATC-3' are used for RNase H activity assays Human immunodeficiency virus type 1 group M subtype B BH10 ?
-
 ?

Synonyms

Synonyms Comment Organism
HIV RT-associated RNase H
-
 Human immunodeficiency virus type 1 group M subtype B
HIV-1 ribonuclease H
-
 Human immunodeficiency virus type 1 group M subtype B
reverse transcriptase-associated ribonuclease H
-
 Human immunodeficiency virus type 1 group M subtype B
reverse transcriptase-associated RNase H
-
 Human immunodeficiency virus type 1 group M subtype B

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Human immunodeficiency virus type 1 group M subtype B

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.8
-
 assay at Human immunodeficiency virus type 1 group M subtype B

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00084
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(3,4-dihydroxybenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.001507
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-hydroxy-6-methoxy-N-(3-(pyridin-2-ylcarbamoyl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-2-yl)nicotinamide
0.004
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B NSC727447
0.00401
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(3,4-dimethoxybenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.00457
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(2-bromobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.00472
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(4-fluorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0075
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(2-chloro-4-fluorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0099
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(2-(2-fluorophenyl)acetamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0099
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-[3-(4-chlorophenyl)propanamido]-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.01036
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B N-(pyridin-2-yl)-2-(thiophene-2-carboxamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.01224
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(2,4-dichlorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0137
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B N-(3-((2-fluorophenyl)carbamoyl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-2-yl)picolinamide
0.01373
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(2-fluorobenzamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.01425
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(2-methoxybenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0145
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-[3-(4-fluorophenyl)propanamido]-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0146
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(3-phenylpropanamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0148
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-benzamido-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.01488
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(2-aminobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.01644
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B N-(pyridin-2-yl)-2-[2-(quinolin-6-yl)acetamido]-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0166
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-[(cyclohexanecarbonyl)amino]-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.01778
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(4-chlorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0183
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(2-methylbenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0201
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-amino-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.02047
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(3-fluorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.02047
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(4-nitrobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.02143
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(4-aminobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0215
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2,6-dimethoxy-N-(3-(pyridin-2-ylcarbamoyl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-2-yl)nicotinamide
0.02189
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(2-fluorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0239
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(2-chlorobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0252
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B ethyl 2-(2-fluorobenzamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate
0.05348
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(2-nitrobenzamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.0671
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(2-cyclohexylacetamido)-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide
0.07258
-
 pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B ethyl 2-(4-chlorobenzamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate
0.1
-
 above, pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-(2-fluorobenzamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid
0.1
-
 above, pH 7.8, 37°C Human immunodeficiency virus type 1 group M subtype B 2-acetamido-N-(pyridin-2-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide