2-(4-diethoxymethylphenyl)-1H-benzimidazole-4-carboxamide | 936551-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(4-diethoxymethylphenyl)-1H-benzimidazole-4-carboxamide
• 英文别名: 2-[4-(diethoxymethyl)phenyl]-1H-benzimidazole-4-carboxamide
• CAS: 936551-77-8
• 化学式: C₁₉H₂₁N₃O₃
• 分子量: 339.394
• InChiKey: ZBCLRQGZTNJFFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  90.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-diethoxymethylphenyl)-1H-benzimidazole-4-carboxamide 在 盐酸 、 sodium tetrahydroborate 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 生成 2-(4-Chloromethyl-phenyl)-1H-benzoimidazole-4-carboxylic acid amide
  参考文献：
  名称：

  Potentiation of cytotoxic drug activity in human tumour cell lines, by amine-substituted 2-arylbenzimidazole-4-carboxamide PARP-1 inhibitors

  摘要：

  The synthesis and biological evaluation of a new series of amine-substituted 2-arylbenzimidazole-4-carboxamide inhibitors of the DNA-repair enzyme poly(ADP-ribose) polymerase-1 (PARP-1) is reported. The introduction of an amine substituent at the 2-aryl position is not detrimental to activity, with most inhibitors exhibiting K-i values for PARP-1 inhibition in the low nanomolar range. Two compounds in this series were found to potentiate the cytotoxicity of the DNA-methylating agent temozolomide by 4-5-fold in a human colorectal cancer cell line. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.03.017
• 作为产物：
  描述：

  2-氨基-3-硝基苯甲酰胺 在 palladium on activated charcoal 氢气 、 sodium hydrogensulfite 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 5.0h， 生成 2-(4-diethoxymethylphenyl)-1H-benzimidazole-4-carboxamide
  参考文献：
  名称：

  Potentiation of cytotoxic drug activity in human tumour cell lines, by amine-substituted 2-arylbenzimidazole-4-carboxamide PARP-1 inhibitors

  摘要：

  The synthesis and biological evaluation of a new series of amine-substituted 2-arylbenzimidazole-4-carboxamide inhibitors of the DNA-repair enzyme poly(ADP-ribose) polymerase-1 (PARP-1) is reported. The introduction of an amine substituent at the 2-aryl position is not detrimental to activity, with most inhibitors exhibiting K-i values for PARP-1 inhibition in the low nanomolar range. Two compounds in this series were found to potentiate the cytotoxicity of the DNA-methylating agent temozolomide by 4-5-fold in a human colorectal cancer cell line. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.03.017

文献信息

• SUBSTITUTED 1H-BENZIMIDAZOLE-4-CARBOXAMIDES ARE POTENT PARP INHIBITORS
  申请人：Giranda Vincent L.

  公开号：US20070259937A1

  公开（公告）日：2007-11-08

  The present invention relates to 1H-benzimidazole-4-carboxamides of formula (I), their preparation, and their use as inhibitors of the enzyme poly(ADP-ribose)polymerase for the preparation of drugs.

  本发明涉及式(I)的1H-苯并咪唑-4-甲酰胺、其制备以及作为聚(ADP-核糖)聚合酶的抑制剂以制备药物的用途。
• US7462724B2
  申请人：——

  公开号：US7462724B2

  公开（公告）日：2008-12-09
• US7595406B2
  申请人：——

  公开号：US7595406B2

  公开（公告）日：2009-09-29
• US7999117B2
  申请人：——

  公开号：US7999117B2

  公开（公告）日：2011-08-16
• [EN] SUBSTITUTED 1H-BENZIMIDAZOLE-4-CARBOXAMIDES ARE POTENT PARP INHIBITORS<br/>[FR] 1H-BENZIMIDAZOLE-4-CARBOXAMIDES SUBSTITUES EFFICACES EN TANT QU'INHIBITEURS DE PARP
  申请人：ABBOTT LAB

  公开号：WO2007059230A2

  公开（公告）日：2007-05-24

  [EN] Compounds of Formula (I) inhibit the PARP enzyme and are useful for treating a disease or a disorder associated with PARP. Also disclosed are pharmaceutical compositions comprising compounds of Formula (I), methods of treatment comprising compounds of Formula (I), and methods of inhibiting the PARP enzyme comprising compounds of Formula (I).
  [FR] L'invention concerne des composés répondant à la formule (I) inhibant l'enzyme PARP et utiles dans le traitement d'une pathologie ou d'un trouble associé à PARP. L'invention concerne également des compositions pharmaceutiques comprenant des composés répondant à la formule (I), des procédés de traitement comprenant des composés répondant à la formule (I) et des procédés d'inhibition de l'enzyme PARP comprenant des composés répondant à la formule (I).