5,5-dioxo-N-(2-pyrazol-1-ylphenyl)dibenzothiophene-4-carboxamide | 883120-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 5,5-dioxo-N-(2-pyrazol-1-ylphenyl)dibenzothiophene-4-carboxamide
• CAS: 883120-77-2
• 化学式: C₂₂H₁₅N₃O₃S
• 分子量: 401.445
• InChiKey: GOSMUWDRAYKZLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-pyrazol-1-ylphenyl)dibenzothiophene-4-carboxamide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 5-oxo-N-(2-pyrazol-1-ylphenyl)dibenzothiophene-4-carboxamide 、 5,5-dioxo-N-(2-pyrazol-1-ylphenyl)dibenzothiophene-4-carboxamide
  参考文献：
  名称：

  Discovery of N-aryl-9-oxo-9H-fluorene-1-carboxamides as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 2. Structure–activity relationships of the 9-oxo-9H-fluorene ring

  摘要：

  As a continuation of our studies of apoptosis inducing 9-oxo-9H-fluorene-1-carboxamides as potential anticancer agents, we explored modi. cation of the 9-oxo-9H-fluorene ring. SAR studies showed that most changes to the 9-oxo-9H-fluorene ring were not well tolerated, except the 9H-fluorene (2b) and dibenzothiophene (2d) analogs, which were about twofold less active than the 9-oxo-9H-fluorene analog 2a. Significantly, introduction of substitutions at the 7-position of the 9-oxo-9H-fluorene ring led to compounds 5a-5c with improved activity. Compound 5a was found to have EC50 values of 0.15-0.29 mu M against T47D, HCT116, and SNU398 cells, about fivefold more potent than the original lead 2a. As opposed to the original lead compound 2a, compounds 5a-5b were active in a tubulin inhibition assay, indicating a change of mechanism of action. The potent azido analog 5c could be utilized for target identification. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.11.025