3-(4-chlorobenzamido)-N-(4-chlorobenzyl)-4,9-dioxo-2,3,4,9-tetrahydronaphtho[2,3-b]thiophene-3-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-chlorobenzamido)-N-(4-chlorobenzyl)-4,9-dioxo-2,3,4,9-tetrahydronaphtho[2,3-b]thiophene-3-carboxamide
• 英文别名: 3-[(4-chlorobenzoyl)amino]-N-[(4-chlorophenyl)methyl]-4,9-dioxo-2H-benzo[f][1]benzothiole-3-carboxamide
• 化学式: C₂₇H₁₈Cl₂N₂O₄S
• 分子量: 537.423
• InChiKey: FJKLNTLROKNEJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对氯苄胺 在 盐酸 、 aluminum oxide 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 3-(4-chlorobenzamido)-N-(4-chlorobenzyl)-4,9-dioxo-2,3,4,9-tetrahydronaphtho[2,3-b]thiophene-3-carboxamide
  参考文献：
  名称：

  Dihydrithieno[2,3-b]naphto-4,9-dione analogues as anticancer agents: Synthesis and in cell pharmacological studies

  摘要：

  The synthesis of a series of highly functionalized DNTQ-based derivatives is described. In vitro, most of the compounds exerted a cytotoxic effect against several tumour cell lines comparable to or greater than that of doxorubicin. Here we demonstrate that compound 14, the less cardiotoxic compound of this series, induced cell differentiation and was distributed mainly in the cytoplasm in the human glioblastoma LN229 cell line. Moreover, compound 14 reduced both cellular glucose uptake and serine/threonine kinase ART expression, and triggered cell apoptosis. These findings suggest that highly functionalized DTNQ-based derivatives are promising pharmacological tools for the study of human solid tumours. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.044