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Literature summary extracted from

  • Wang, H.; Yu, N.; Song, H.; Chen, D.; Zou, Y.; Deng, W.; Lye, P.L.; Chang, J.; Ng, M.; Sun, E.T.; Sangthongpitag, K.; Wang, X.; Wu, X.; Khng, H.H.; Fang, L.; Goh, S.K.; Ong, W.C.; Bonday, Z.; Stuenkel, W.; Poulsen, A.; Entzeroth, M.
    N-Hydroxy-1,2-disubstituted-1H-benzimidazol-5-yl acrylamides as novel histone deacetylase inhibitors: Design, synthesis, SAR studies, and in vivo antitumor activity (2009), Bioorg. Med. Chem. Lett., 19, 1403-1408.
    View publication on PubMed

Application

EC Number Application Comment Organism
3.5.1.98 medicine a representative compound, (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1-(2-pyrrolidin-1-ylethyl)-1H-benzimidazol-5-yl]prop-2-enamide, SB639, has demonstrated antitumor activity in a colon cancer xenograft model Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.5.1.98 (2E)-3-[1,2-bis(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-3-[1-benzyl-2-(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-3-[1-benzyl-2-(2-phenylethyl)-1H-benzimidazol-6-yl]-N-hydroxyprop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-3-[1-ethyl-2-(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-3-[1-[2-(diethylamino)ethyl]-2-(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-3-[1-[3-(dimethylamino)-2,2-dimethylpropyl]-2-(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-3-[1-[3-(dimethylamino)propyl]-2-(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-3-[1-[4-(dimethylamino)butyl]-2-(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-3-[2-cyclohexyl-1-(3-hydroxypropyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-3-[2-[(benzyloxy)methyl]-1-(3-hydroxypropyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-(2-aminophenyl)-3-[2-(2-phenylethyl)-1-(pyridin-2-ylmethyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[1-(2-morpholin-4-ylethyl)-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-2-(1-methylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-2-(2-methylpropyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-2-(2-phenylpropyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-2-octyl-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-2-thiophen-3-yl-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[1-(3-methoxypropyl)-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[1-(3-morpholin-4-ylpropyl)-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[1-methyl-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[1-[3-(1H-imidazol-1-yl)propyl]-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[1-[3-(2-oxopyrrolidin-1-yl)propyl]-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1-(2-piperidin-1-ylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1-(2-pyrrolidin-1-ylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1-(3,4,5-trimethoxybenzyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1-(3-pyrrolidin-1-ylpropyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1-(pyridin-2-ylmethyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1-propyl-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
-
 Homo sapiens
3.5.1.98 3-[5-[(1E)-3-(hydroxyamino)-3-oxoprop-1-en-1-yl]-2-(2-phenylethyl)-1H-benzimidazol-1-yl]propanoic acid
-
 Homo sapiens
3.5.1.98 belinostat PXD101 Homo sapiens
3.5.1.98 entinostat MS-275 Homo sapiens
3.5.1.98 N-hydroxy-1-(3-hydroxypropyl)-2-(2-phenylethyl)-1H-benzimidazole-5-carboxamide
-
 Homo sapiens
3.5.1.98 N-hydroxy-2-[1-methyl-2-(2-phenylethyl)-1H-benzimidazol-5-yl]cyclopropanecarboxamide
-
 Homo sapiens
3.5.1.98 N-hydroxy-3-[1-(3-hydroxypropyl)-2-(2-methylpropyl)-1H-benzimidazol-5-yl]propanamide
-
 Homo sapiens
3.5.1.98 N-hydroxy-3-[2-(2-phenylethyl)-1-(3,4,5-trimethoxybenzyl)-1H-benzimidazol-5-yl]propanamide
-
 Homo sapiens
3.5.1.98 romidepsin FK228 Homo sapiens
3.5.1.98 vorinostat SAHA Homo sapiens

Organism

EC Number Organism UniProt Comment Textmining
3.5.1.98 Homo sapiens
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.5.1.98 A-2780 cell
-
 Homo sapiens
-
3.5.1.98 HCT-116 cell
-
 Homo sapiens
-
3.5.1.98 PC-3 cell
-
 Homo sapiens
-

Synonyms

EC Number Synonyms Comment Organism
3.5.1.98 HDAC1
-
 Homo sapiens
3.5.1.98 histone deacetylase
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.5.1.98 0.000026
-
-
 Homo sapiens (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1-(2-piperidin-1-ylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.000035
-
-
 Homo sapiens (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1-(2-pyrrolidin-1-ylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.000041
-
-
 Homo sapiens (2E)-3-[1-[3-(dimethylamino)-2,2-dimethylpropyl]-2-(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
3.5.1.98 0.000047
-
-
 Homo sapiens (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1-(3,4,5-trimethoxybenzyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.000052
-
-
 Homo sapiens (2E)-3-[1-[2-(diethylamino)ethyl]-2-(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
3.5.1.98 0.00008
-
-
 Homo sapiens (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-2-(2-phenylpropyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.0001
-
-
 Homo sapiens (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-2-(2-methylpropyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.00016
-
-
 Homo sapiens (2E)-3-[1-[4-(dimethylamino)butyl]-2-(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
3.5.1.98 0.00016
-
-
 Homo sapiens (2E)-N-hydroxy-3-[1-[3-(1H-imidazol-1-yl)propyl]-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.00017
-
-
 Homo sapiens (2E)-3-[2-[(benzyloxy)methyl]-1-(3-hydroxypropyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
3.5.1.98 0.00017
-
-
 Homo sapiens (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.00017
-
-
 Homo sapiens (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1-propyl-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.00017
-
-
 Homo sapiens (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.00017
-
-
 Homo sapiens N-hydroxy-3-[2-(2-phenylethyl)-1-(3,4,5-trimethoxybenzyl)-1H-benzimidazol-5-yl]propanamide
3.5.1.98 0.00019
-
-
 Homo sapiens (2E)-3-[1-[3-(dimethylamino)propyl]-2-(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
3.5.1.98 0.0002
-
-
 Homo sapiens (2E)-N-hydroxy-3-[1-[3-(2-oxopyrrolidin-1-yl)propyl]-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.00021
-
-
 Homo sapiens (2E)-N-hydroxy-3-[1-(3-methoxypropyl)-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.00022
-
-
 Homo sapiens (2E)-3-[1-ethyl-2-(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
3.5.1.98 0.00025
-
-
 Homo sapiens (2E)-N-hydroxy-3-[1-(3-morpholin-4-ylpropyl)-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.00025
-
-
 Homo sapiens (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1-(pyridin-2-ylmethyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.00026
-
-
 Homo sapiens (2E)-N-hydroxy-3-[1-methyl-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.00027
-
-
 Homo sapiens (2E)-N-hydroxy-3-[1-(2-morpholin-4-ylethyl)-2-(2-phenylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.00031
-
-
 Homo sapiens (2E)-N-hydroxy-3-[2-(2-phenylethyl)-1-(3-pyrrolidin-1-ylpropyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.00041
-
-
 Homo sapiens (2E)-3-[1-benzyl-2-(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
3.5.1.98 0.00053
-
-
 Homo sapiens (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-2-octyl-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.00088
-
-
 Homo sapiens (2E)-3-[1,2-bis(2-phenylethyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
3.5.1.98 0.0011
-
-
 Homo sapiens (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.0012
-
-
 Homo sapiens (2E)-3-[1-benzyl-2-(2-phenylethyl)-1H-benzimidazol-6-yl]-N-hydroxyprop-2-enamide
3.5.1.98 0.0013
-
-
 Homo sapiens N-hydroxy-2-[1-methyl-2-(2-phenylethyl)-1H-benzimidazol-5-yl]cyclopropanecarboxamide
3.5.1.98 0.0017
-
-
 Homo sapiens (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-2-(1-methylethyl)-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.0019
-
-
 Homo sapiens (2E)-N-hydroxy-3-[1-(3-hydroxypropyl)-2-thiophen-3-yl-1H-benzimidazol-5-yl]prop-2-enamide
3.5.1.98 0.0023
-
-
 Homo sapiens 3-[5-[(1E)-3-(hydroxyamino)-3-oxoprop-1-en-1-yl]-2-(2-phenylethyl)-1H-benzimidazol-1-yl]propanoic acid
3.5.1.98 0.0032
-
-
 Homo sapiens (2E)-3-[2-cyclohexyl-1-(3-hydroxypropyl)-1H-benzimidazol-5-yl]-N-hydroxyprop-2-enamide
3.5.1.98 0.0033
-
-
 Homo sapiens N-hydroxy-1-(3-hydroxypropyl)-2-(2-phenylethyl)-1H-benzimidazole-5-carboxamide
3.5.1.98 0.01
-
 larger than 0.010 Homo sapiens N-hydroxy-3-[1-(3-hydroxypropyl)-2-(2-methylpropyl)-1H-benzimidazol-5-yl]propanamide
3.5.1.98 0.1
-
 larger than 0.10 Homo sapiens (2E)-N-(2-aminophenyl)-3-[2-(2-phenylethyl)-1-(pyridin-2-ylmethyl)-1H-benzimidazol-5-yl]prop-2-enamide