N-(6-nitro-1H-benzimidazol-2-yl)-1-benzofuran-2-carboxamide | 1422390-98-4

• 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-(6-nitro-1H-benzimidazol-2-yl)-1-benzofuran-2-carboxamide
• CAS: 1422390-98-4
• 化学式: C₁₆H₁₀N₄O₄
• 分子量: 322.28
• InChiKey: QAICUDUALKIEIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基-6-硝基苯并咪唑 、 1-苯并呋喃-2-羰酰氯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以68%的产率得到N-(6-nitro-1H-benzimidazol-2-yl)-1-benzofuran-2-carboxamide
  参考文献：
  名称：

  Antiproliferative potency of novel benzofuran-2-carboxamides on tumour cell lines: Cell death mechanisms and determination of crystal structure

  摘要：

  In this manuscript the synthesis and biological activity of novel heterocyclic derivatives of benzofuran-2-carboxamides 3a-j and 6a-f is presented. Biological evaluation in vitro revealed that only few compounds exerted concentration-depended antiproliferative effects on tumour cell lines at micromolar concentrations. In particular, 2-imidazolynyl substituted compound 6f showed selectivity on SK-BR-3 cell line while 2-N-acetamidopyridyl substituted 3h and 2-imidazolynyl substituted amide 3i showed selective concentration-dependent antiproliferative effects on SW620 cell line. Compounds 3h and 61 induced apoptosis while compound 3i acted through a cell death mechanism other than apoptosis. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.009

文献信息

• Antiproliferative potency of novel benzofuran-2-carboxamides on tumour cell lines: Cell death mechanisms and determination of crystal structure
  作者：Marijana Hranjec、Irena Sović、Ivana Ratkaj、Gordana Pavlović、Nataša Ilić、Linda Valjalo、Krešimir Pavelić、Sandra Kraljević Pavelić、Grace Karminski-Zamola

  DOI：10.1016/j.ejmech.2012.11.009

  日期：2013.1

  In this manuscript the synthesis and biological activity of novel heterocyclic derivatives of benzofuran-2-carboxamides 3a-j and 6a-f is presented. Biological evaluation in vitro revealed that only few compounds exerted concentration-depended antiproliferative effects on tumour cell lines at micromolar concentrations. In particular, 2-imidazolynyl substituted compound 6f showed selectivity on SK-BR-3 cell line while 2-N-acetamidopyridyl substituted 3h and 2-imidazolynyl substituted amide 3i showed selective concentration-dependent antiproliferative effects on SW620 cell line. Compounds 3h and 61 induced apoptosis while compound 3i acted through a cell death mechanism other than apoptosis. (C) 2012 Elsevier Masson SAS. All rights reserved.