5-chloro-3-((3,5-dimethylphenyl)sulfonyl)-N-(quinolin-4-ylmethyl)-1H-indole-2-carboxamide | 1384118-27-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-chloro-3-((3,5-dimethylphenyl)sulfonyl)-N-(quinolin-4-ylmethyl)-1H-indole-2-carboxamide
• 英文别名: 5-chloro-3-(3,5-dimethylphenyl)sulfonyl-N-(4-quinolylmethyl)-1H-indole-2-carboxamide；5-chloro-3-(3,5-dimethylphenyl)sulfonyl-N-(quinolin-4-ylmethyl)-1H-indole-2-carboxamide
• CAS: 1384118-27-7
• 化学式: C₂₇H₂₂ClN₃O₃S
• 分子量: 504.009
• InChiKey: PNNRHGBAXQYSIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  35
• 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：
  100
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氨基甲基喹啉盐酸盐 、 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35%的产率得到5-chloro-3-((3,5-dimethylphenyl)sulfonyl)-N-(quinolin-4-ylmethyl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  New Nitrogen Containing Substituents at the Indole-2-carboxamide Yield High Potent and Broad Spectrum Indolylarylsulfone HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors

  摘要：

  New indolylarylsulfone (IAS) derivatives bearing nitrogen containing substituents at the indole-2-carboxamide inhibited the HIV-1 WT in MT-4 cells at low nanomolar concentrations. In particular, compound 9 was uniformly effective against the mutant Y181C, Y188L, and K103N HIV-1 strains; it was highly active against the multidrug resistant mutant IRLL98 HIV-1 strain bearing the K101Q, Y181C, and G190A mutations conferring resistance to NVP, DLV, and EFV and several HIV-1 clades A in PBMC.

  DOI：

  10.1021/jm300477h

文献信息

• New Nitrogen Containing Substituents at the Indole-2-carboxamide Yield High Potent and Broad Spectrum Indolylarylsulfone HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors
  作者：Giuseppe La Regina、Antonio Coluccia、Andrea Brancale、Francesco Piscitelli、Valeria Famiglini、Sandro Cosconati、Giovanni Maga、Alberta Samuele、Emmanuel Gonzalez、Bonaventura Clotet、Dominique Schols、José A. Esté、Ettore Novellino、Romano Silvestri

  DOI：10.1021/jm300477h

  日期：2012.7.26

  New indolylarylsulfone (IAS) derivatives bearing nitrogen containing substituents at the indole-2-carboxamide inhibited the HIV-1 WT in MT-4 cells at low nanomolar concentrations. In particular, compound 9 was uniformly effective against the mutant Y181C, Y188L, and K103N HIV-1 strains; it was highly active against the multidrug resistant mutant IRLL98 HIV-1 strain bearing the K101Q, Y181C, and G190A mutations conferring resistance to NVP, DLV, and EFV and several HIV-1 clades A in PBMC.