N-hydroxy-3-[3-(1-methylbenzimidazol-2-yl)phenyl]prop-2-enamide | 758693-28-6

• 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: N-hydroxy-3-[3-(1-methylbenzimidazol-2-yl)phenyl]prop-2-enamide
• CAS: 758693-28-6
• 化学式: C₁₇H₁₅N₃O₂
• 分子量: 293.325
• InChiKey: RWDIFWLNAIKKCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 camphorsulfonic acid 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 N-hydroxy-3-[3-(1-methylbenzimidazol-2-yl)phenyl]prop-2-enamide
  参考文献：
  名称：

  Benzimidazole and imidazole inhibitors of histone deacetylases: Synthesis and biological activity

  摘要：

  A series of N-hydroxy-3-[3-(1-substituted-1H-benzoimidazol-2-yl)-phenyl]-acrylamides (5a-5ab) and N-hydroxy-3-[ 3-( 1,4,5-trisubstituted-1H-imidazol-2-yl)-phenyl]-acrylamides (12a-s) were designed, synthesized, and found to be nanomolar inhibitors of human histone deacetylases. Multiple compounds bearing an N1-piperidine demonstrate EC(50)s of 20-100 nM in human A549, HL60, and PC3 cells, in vitro and in vivo hyperacetylation of histones H3 and H4, and induction of p21(waf). Compound 5x displays efficacy in human tumor xenograft models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.092

文献信息

• Histone deacetylase inhibitors
  申请人：Syrrx, Inc.

  公开号：US20040266769A1

  公开（公告）日：2004-12-30

  Compounds that may be used to inhibit histone deacetylase having the formula Z-Q-L-M or Z-L-M wherein M is a substituent capable of complexing with a deacetylase catalytic site and/or a metal ion; L is a substituent providing between 0-10 atoms separation between the M substituent and the remainder of the compound; and Z and Q are as defined herein.

  可能用于抑制组蛋白去乙酰化酶的化合物具有以下公式：Z-Q-L-M或Z-L-M，其中M是一个能够与去乙酰化酶催化位点和/或金属离子形成配合物的取代基；L是一个提供M取代基和化合物其余部分之间介于0-10个原子的取代基；Z和Q的定义如下。
• HISTONE DEACETYLASE INHIBITORS
  申请人：Takeda San Diego, Inc.

  公开号：EP1608628A2

  公开（公告）日：2005-12-28
• US7169801B2
  申请人：——

  公开号：US7169801B2

  公开（公告）日：2007-01-30
• [EN] HISTONE DEACETYLASE INHIBITORS<br/>[FR] INHIBITEURS D'HISTONE DEACETYLASE
  申请人：SYRRX INC

  公开号：WO2004082638A2

  公开（公告）日：2004-09-30

  Compounds that may be used to inhibit histone deacetylase having the formula (I) or formula (II) wherein M is a substituent capable of complexing with a deacetylase catalytic site and/or a metal ion; L is a substituent providing between 0-10 atoms separation between the M substituent and the remainder of the compound; and Z and Q are as defined herein.