2-(benzimidazol-1-yl)-N-[hydroxy-(5-nitrofuran-2-yl)methyl]acetamide | 1078734-61-8

• 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-(benzimidazol-1-yl)-N-[hydroxy-(5-nitrofuran-2-yl)methyl]acetamide
• CAS: 1078734-61-8
• 化学式: C₁₄H₁₂N₄O₅
• 分子量: 316.273
• InChiKey: KFKIIAOVJGRNFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-硝基糠醛 、 (9ci)-1H-苯并咪唑-1-乙酰胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以22%的产率得到2-(benzimidazol-1-yl)-N-[hydroxy-(5-nitrofuran-2-yl)methyl]acetamide
  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.