5,6-dichloro-3-(3,5-dimethylbenzenesulfonyl)indole-2-carboxylic acid amide

• 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: 5,6-dichloro-3-(3,5-dimethylbenzenesulfonyl)indole-2-carboxylic acid amide
• 英文别名: 5,6-dichloro-3-(3,5-dimethylphenyl)sulfonyl-1H-indole-2-carboxamide
• 化学式: C₁₇H₁₄Cl₂N₂O₃S
• 分子量: 397.282
• InChiKey: QIGZWKYITXFOJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 5,6-dichloro-3-[(3,5-dimethylphenyl)sulfonyl]-1H-indole-2-carboxylate 在 ammonium hydroxide 、 氯化铵 作用下， 以43%的产率得到5,6-dichloro-3-(3,5-dimethylbenzenesulfonyl)indole-2-carboxylic acid amide
  参考文献：
  名称：

  Indolyl Aryl Sulfones as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors:  Role of Two Halogen Atoms at the Indole Ring in Developing New Analogues with Improved Antiviral Activity

  摘要：

  Indolyl aryl sulfones bearing the 4,5-difluoro (10) or 5-chloro-4-fluoro (16) substitution pattern at the indole ring were potent inhibitors of HIV-1 WT and the NNRTI-resistant strains Y181C and K103N-Y181C. These compounds were highly effective against the 112 and the AB1 strains in lymphocytes and inhibited at nanomolar concentration the multiplication of the IIIBBa-L strain in macrophages. Compound 16 was exceptionally potent against RT WT and RTs carrying the K103N, Y181I, and L100I mutations.

  DOI：

  10.1021/jm070488f

文献信息

• Phenylindoles for the treatment of HIV
  申请人：——

  公开号：US20020193415A1

  公开（公告）日：2002-12-19

  The invention as disclosed herein is a method and composition for the treatment of HIV in humans and other host animals, that includes the administration of an effective HIV treatment amount of a phenylindole as described herein or a pharmaceutically acceptable salt or prodrug thereof, optionally in a pharmaceutically acceptable carrier. The compounds of this invention either possess antiviral (i.e., anti-HIV) activity, or are metabolized to a compound that exhibits such activity.

  本发明公开了一种用于治疗人类和其他宿主动物体内的HIV的方法和组合物，包括根据本文所述的给予有效的HIV治疗量的苯基吲哚或其药学上可接受的盐或前药，可选地在药学上可接受的载体中。本发明的化合物具有抗病毒（即抗HIV）活性，或者经代谢后形成具有该活性的化合物。
• PHENYLINDOLES FOR THE TREATMENT OF HIV
  申请人：Idenix (Cayman) Limited

  公开号：EP1390029B1

  公开（公告）日：2009-12-16
• US6710068B2
  申请人：——

  公开号：US6710068B2

  公开（公告）日：2004-03-23
• Indolyl Aryl Sulfones as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors:  Role of Two Halogen Atoms at the Indole Ring in Developing New Analogues with Improved Antiviral Activity
  作者：Giuseppe La Regina、Antonio Coluccia、Francesco Piscitelli、Alberto Bergamini、Anna Sinistro、Antonella Cavazza、Giovanni Maga、Alberta Samuele、Samantha Zanoli、Ettore Novellino、Marino Artico、Romano Silvestri

  DOI：10.1021/jm070488f

  日期：2007.10.1

  Indolyl aryl sulfones bearing the 4,5-difluoro (10) or 5-chloro-4-fluoro (16) substitution pattern at the indole ring were potent inhibitors of HIV-1 WT and the NNRTI-resistant strains Y181C and K103N-Y181C. These compounds were highly effective against the 112 and the AB1 strains in lymphocytes and inhibited at nanomolar concentration the multiplication of the IIIBBa-L strain in macrophages. Compound 16 was exceptionally potent against RT WT and RTs carrying the K103N, Y181I, and L100I mutations.