(E)-2-(1H-benzimidazol-2-yl)-3-thiophen-3-ylprop-2-enenitrile

• 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: (E)-2-(1H-benzimidazol-2-yl)-3-thiophen-3-ylprop-2-enenitrile
• 化学式: C₁₄H₉N₃S
• 分子量: 251.312
• InChiKey: WZXXDFREJIPPRV-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-噻吩甲醛 、 2-氰甲基苯并咪唑 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.5h， 以51%的产率得到(E)-2-(1H-benzimidazol-2-yl)-3-thiophen-3-ylprop-2-enenitrile
  参考文献：
  名称：

  Structure–activity relationships of novel heteroaryl-acrylonitriles as cytotoxic and antibacterial agents

  摘要：

  Eighteen new 2,6-disubstituted acrylonitriles and two new (benzimidazol-1-yl)-acetamide derivatives were prepared and screened for antibacterial and cytotoxic activities on 12 human cancer cell lines. Based on the lead structure 2-(benzimidazol-2-yl)-3-(5-nitrothiophen-2-yl) acrylonitrile it was found that placement of methyl groups at the 5,6 positions of the benzimidazole ring lead to a 3-fold increase in overall cytotoxic activity. Replacing the nitrothiophene for pyridine reduced cytotoxic activity as did replacing the nitro group for a methoxy group. Cytotoxic activity was only slightly reduced when the benzimidazole ring was replaced by a imidazo[4,5-b]pyridine or a benzthiazole ring but replacement by benzoxazole led to a substantial decrease in activity. Moving the acrylonitrile group from position 2 to position 1 of the benzimidazole ring also resulted in moderately active compounds. (Benzimidazol-1-yl)acetamides showed only modest activity. The structure-activity relationships found in the cytotoxicity studies are mirrored in the results of the antibacterial experiments. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.11.017

文献信息

• Structure–activity relationships of novel heteroaryl-acrylonitriles as cytotoxic and antibacterial agents
  作者：Franciszek Sączewski、Agnieszka Stencel、Andrzej M. Bieńczak、Karolina A. Langowska、Martin Michaelis、Władysław Werel、Rafał Hałasa、Przemyslaw Reszka、Patrick J. Bednarski

  DOI：10.1016/j.ejmech.2007.11.017

  日期：2008.9

  Eighteen new 2,6-disubstituted acrylonitriles and two new (benzimidazol-1-yl)-acetamide derivatives were prepared and screened for antibacterial and cytotoxic activities on 12 human cancer cell lines. Based on the lead structure 2-(benzimidazol-2-yl)-3-(5-nitrothiophen-2-yl) acrylonitrile it was found that placement of methyl groups at the 5,6 positions of the benzimidazole ring lead to a 3-fold increase in overall cytotoxic activity. Replacing the nitrothiophene for pyridine reduced cytotoxic activity as did replacing the nitro group for a methoxy group. Cytotoxic activity was only slightly reduced when the benzimidazole ring was replaced by a imidazo[4,5-b]pyridine or a benzthiazole ring but replacement by benzoxazole led to a substantial decrease in activity. Moving the acrylonitrile group from position 2 to position 1 of the benzimidazole ring also resulted in moderately active compounds. (Benzimidazol-1-yl)acetamides showed only modest activity. The structure-activity relationships found in the cytotoxicity studies are mirrored in the results of the antibacterial experiments. (C) 2007 Elsevier Masson SAS. All rights reserved.