N-(3-aminophenyl)-5-chloro-3-((3,5-dimethylphenyl)sulfonyl)-1H-indole-2-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: N-(3-aminophenyl)-5-chloro-3-((3,5-dimethylphenyl)sulfonyl)-1H-indole-2-carboxamide
• 英文别名: N-(3-aminophenyl)-5-chloro-3-(3,5-dimethylphenyl)sulfonyl-1H-indole-2-carboxamide
• 化学式: C₂₃H₂₀ClN₃O₃S
• 分子量: 453.949
• InChiKey: OUUGHQCLGQFHKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  间苯二胺 、 5-氯-3-((3,5-二甲基苯基)磺酰基)-1H-吲哚-2-羧酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以52%的产率得到N-(3-aminophenyl)-5-chloro-3-((3,5-dimethylphenyl)sulfonyl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  Indolylarylsulfones Carrying a Heterocyclic Tail as Very Potent and Broad Spectrum HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  We synthesized new indolylarylsulfone (IAS) derivatives carrying a heterocyclic tail at the indole-2-carboxamide nitrogen as potential anti-HIV/AIDS agents. Several new IASs yielded EC50 values <1.0 nM against HIV-1 WT and mutant strains in MT-4 cells. The (R)-11 enantiomer proved to be exceptionally potent against the whole viral panel; in the reverse transcriptase (RT) screening assay, it was remarkably superior to NVP and EFV and comparable to ETV. The binding poses were consistent with the one previously described for the IAS non-nucleoside reverse transcriptase inhibitors. Docking studies showed that the methyl group of (R)-11 points toward the cleft created by the K103N mutation, different from the corresponding group of (S)-11. By calculating the solvent-accessible surface, we observed that the exposed area of RT in complex with (S)-11 was larger than the area of the (R)-11 complex. Compounds 6 and 16 and enantiomer (R)-11 represent novel robust lead compounds of the IAS class.

  DOI：

  10.1021/jm5011622