2-(2,4-dichloro-phenyl)-7-methoxy-1H-benzoimidazole-4-carboxylic acid methyl ester | 733754-25-1

• 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-(2,4-dichloro-phenyl)-7-methoxy-1H-benzoimidazole-4-carboxylic acid methyl ester
• 英文别名: methyl 2-(2,4-dichlorophenyl)-7-methoxy-1H-benzimidazole-4-carboxylate
• CAS: 733754-25-1
• 化学式: C₁₆H₁₂Cl₂N₂O₃
• 分子量: 351.189
• InChiKey: DVUQFRYJTPTUNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,4-dichloro-phenyl)-7-methoxy-1H-benzoimidazole-4-carboxylic acid methyl ester 在 aluminum (III) chloride 、 盐酸 作用下， 以 甲苯 、 水 为溶剂， 反应 8.5h， 以92%的产率得到2-(2,4-dichloro-phenyl)-7-hydroxy-1H-benzimidazole-4-carboxylic acid
  参考文献：
  名称：

  [EN] GLYCOGEN SYNTHASE KINASE 3BETA INHIBITOR, COMPOSITION AND PROCESS FOR THE PREPARATION THEREOF
  [FR] INHIBITEUR DE GLYCOGENE SYNTHASE KINASE 3 DOLLAR G(B), COMPOSITION ET PROCEDE DE PREPARATION ASSOCIE

  摘要：

  具有羟基苯并咪唑羧酰胺的新化合物对抑制糖原合成酶激酶3β（GSK-3β）具有用处。

  公开号：

  WO2004065370A1
• 作为产物：
  描述：

  2,4-二氯苯腈 在 盐酸 、 对甲苯磺酸 作用下， 生成 2-(2,4-dichloro-phenyl)-7-methoxy-1H-benzoimidazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Structure–activity relationship of the 7-hydroxy benzimidazole analogs as glycogen synthase kinase 3β inhibitor

  摘要：

  Design, synthesis and the GSK3 beta inhibitory activities of the 7-hydroxy benzimidazole analogs are described. The solid-phase synthetic route was also developed for preparation of the analogs consisting of the novel ATP competitive scaffold. In addition, the structure-activity relationship of the 7-hydroxy benzimidazole analogs and their biological activities are reported. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.065

文献信息

• Glycogen synthase kinase 3beta inhibitor, composition and process for the preparation thereof
  申请人：Cho Myung Joong

  公开号：US20060079521A1

  公开（公告）日：2006-04-13

  Novel compounds having hydroxybenzoimidazole carboxylic amide are useful for inhibiting glycogen synthase kinase 3β (GSK-3β).

  含有羟基苯并咪唑羧酰胺的新化合物可用于抑制糖原合酶激酶3β (GSK-3β)。
• Glycogen synthase kinase 3β inhibitor, composition and process for the preparation thereof
  申请人：Crystalgenomics, Inc.

  公开号：US07179832B2

  公开（公告）日：2007-02-20

  Novel compounds having hydroxybenzoimidazole carboxylic amide are useful for inhibiting glycogen synthase kinase 3β(GSK-3β).

  含有羟基苯并咪唑羧酰胺的新化合物可用于抑制糖原合成酶激酶3β（GSK-3β）。
• Design and synthesis of 7-hydroxy-1H-benzoimidazole derivatives as novel inhibitors of glycogen synthase kinase-3β
  作者：Dongkyu Shin、Seung-Chul Lee、Yong-Seok Heo、Woon-Young Lee、Yong-Soon Cho、Yong Eun Kim、Young-Lan Hyun、Joong Myung Cho、Yoon Sup Lee、Seonggu Ro

  DOI：10.1016/j.bmcl.2007.07.056

  日期：2007.10

  A hydroxy functional group was introduced as the hydrogen bond donor and acceptor at the hinge region of protein kinase in order to develop novel ATP-competitive inhibitors. Several derivatives of 7-hydroxyl-1H-benzoimidazole were designed as inhibitors of glycogen synthase kinase-3 beta with the help of ab initio calculations and a docking study. Enzymatic assay and an X-ray complex study showed that these designed compounds were highly potent ATP-competitive inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.
• GLYCOGEN SYNTHASE KINASE 3BETA INHIBITOR, COMPOSITION AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Crystalgenomics, Inc.

  公开号：EP1590333A1

  公开（公告）日：2005-11-02
• EP1590333A4
  申请人：——

  公开号：EP1590333A4

  公开（公告）日：2008-04-30