N-[2-(1H-pyrrol-1-yl)ethyl]-3-[(3,5-dimethylphenyl)sulfonyl]-5-nitro-1H-indole-2-carboxamide | 1278586-69-8

• 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: N-[2-(1H-pyrrol-1-yl)ethyl]-3-[(3,5-dimethylphenyl)sulfonyl]-5-nitro-1H-indole-2-carboxamide
• 英文别名: 5-Nitro-3-[(3,5-dimethylphenyl)sulfonyl]-N-(pyrrol-1-ylethyl)-1H-indole-2-carboxamide；3-(3,5-dimethylphenyl)sulfonyl-5-nitro-N-(2-pyrrol-1-ylethyl)-1H-indole-2-carboxamide
• CAS: 1278586-69-8
• 化学式: C₂₃H₂₂N₄O₅S
• 分子量: 466.517
• InChiKey: PQYRXENYFNNRKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(1H-吡咯-1-基)-1-乙胺 、 3-[(3,5-dimethylphenyl)sulfonyl]-5-nitro-1H-indole-2-carboxylic acid 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， 以76%的产率得到N-[2-(1H-pyrrol-1-yl)ethyl]-3-[(3,5-dimethylphenyl)sulfonyl]-5-nitro-1H-indole-2-carboxamide
  参考文献：
  名称：

  Indolylarylsulfones as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors: New Cyclic Substituents at Indole-2-carboxamide

  摘要：

  New indolylarylsulfone derivatives bearing cyclic substituents at indole-2-carboxamide linked through a methylene/ethylene spacer were potent inhibitors of the WT HIV-1 replication in CEM and PBMC cells with inhibitory concentrations in the low nanomolar range. Against the mutant L100I and K103N RT HIV-1 strains in MT-4 cells, compounds 20, 24-26, 36, and 40 showed antiviral potency superior to that of NVP and EFV. Against these mutant strains, derivatives 20, 24-26, and 40 were equipotent to ETV. Molecular docking experiments on this novel series of IAS analogues have also suggested that the H-bond interaction between the nitrogen atom in the carboxamide chain of IAS and Glu138:B is important in the binding of these compounds. These results are in accordance with the experimental data obtained on the WT and on the mutant HIV-1 strains tested.

  DOI：

  10.1021/jm101614j

文献信息

• Indolylarylsulfones as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors: New Cyclic Substituents at Indole-2-carboxamide
  作者：Giuseppe La Regina、Antonio Coluccia、Andrea Brancale、Francesco Piscitelli、Valerio Gatti、Giovanni Maga、Alberta Samuele、Christophe Pannecouque、Dominique Schols、Jan Balzarini、Ettore Novellino、Romano Silvestri

  DOI：10.1021/jm101614j

  日期：2011.3.24

  New indolylarylsulfone derivatives bearing cyclic substituents at indole-2-carboxamide linked through a methylene/ethylene spacer were potent inhibitors of the WT HIV-1 replication in CEM and PBMC cells with inhibitory concentrations in the low nanomolar range. Against the mutant L100I and K103N RT HIV-1 strains in MT-4 cells, compounds 20, 24-26, 36, and 40 showed antiviral potency superior to that of NVP and EFV. Against these mutant strains, derivatives 20, 24-26, and 40 were equipotent to ETV. Molecular docking experiments on this novel series of IAS analogues have also suggested that the H-bond interaction between the nitrogen atom in the carboxamide chain of IAS and Glu138:B is important in the binding of these compounds. These results are in accordance with the experimental data obtained on the WT and on the mutant HIV-1 strains tested.