2-(1H-benzo[d]imidazol-2-yl)-3-(5-methylthiophen-2-yl)acrylonitrile | 391659-76-0

• 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-(1H-benzo[d]imidazol-2-yl)-3-(5-methylthiophen-2-yl)acrylonitrile
• 英文别名: 2-(1H-benzimidazol-2-yl)-3-(5-methylthiophen-2-yl)prop-2-enenitrile
• CAS: 391659-76-0
• 化学式: C₁₅H₁₁N₃S
• 分子量: 265.338
• InChiKey: JTYKDXRADVCINF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-甲基-2-噻吩甲醛 、 2-氰甲基苯并咪唑 在 ammonium acetate 、 溶剂黄146 作用下， 反应 2.0h， 生成 2-(1H-benzo[d]imidazol-2-yl)-3-(5-methylthiophen-2-yl)acrylonitrile
  参考文献：
  名称：

  Time-dependent botulinum neurotoxin serotype A metalloprotease inhibitors

  摘要：

  Botulinum neurotoxins (BoNTs) are the most lethal of biological substances, and are categorized as class A biothreat agents by the Centers for Disease Control and Prevention. There are currently no drugs to treat the deadly flaccid paralysis resulting from BoNT intoxication. Among the seven BoNT serotypes, the development of therapeutics to counter BoNT/A is a priority (due to its long half-life in the neuronal cytosol and its ease of production). In this regard, the BoNT/A enzyme light chain (LC) component, a zinc metalloprotease responsible for the intracellular cleavage of synaptosomal-associated protein of 25 kDa, is a desirable target for developing post-BoNT/A intoxication rescue therapeutics. In an earlier study, we reported the high throughput screening of a library containing 70,000 compounds, and uncovered a novel class of benzimidazole acrylonitrile-based BoNT/A LC inhibitors. Herein, we present both structure-activity relationships and a proposed mechanism of action for this novel inhibitor chemotype. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.062

文献信息

• Time-dependent botulinum neurotoxin serotype A metalloprotease inhibitors
  作者：Bing Li、Steven C. Cardinale、Michelle M. Butler、Ramdas Pai、Jonathan E. Nuss、Norton P. Peet、Sina Bavari、Terry L. Bowlin

  DOI：10.1016/j.bmc.2011.10.062

  日期：2011.12

  Botulinum neurotoxins (BoNTs) are the most lethal of biological substances, and are categorized as class A biothreat agents by the Centers for Disease Control and Prevention. There are currently no drugs to treat the deadly flaccid paralysis resulting from BoNT intoxication. Among the seven BoNT serotypes, the development of therapeutics to counter BoNT/A is a priority (due to its long half-life in the neuronal cytosol and its ease of production). In this regard, the BoNT/A enzyme light chain (LC) component, a zinc metalloprotease responsible for the intracellular cleavage of synaptosomal-associated protein of 25 kDa, is a desirable target for developing post-BoNT/A intoxication rescue therapeutics. In an earlier study, we reported the high throughput screening of a library containing 70,000 compounds, and uncovered a novel class of benzimidazole acrylonitrile-based BoNT/A LC inhibitors. Herein, we present both structure-activity relationships and a proposed mechanism of action for this novel inhibitor chemotype. (C) 2011 Elsevier Ltd. All rights reserved.