5-chloro-3-(diphenylphosphinyl)-1H-indole-2-carboxamide

• 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-(diphenylphosphinyl)-1H-indole-2-carboxamide
• 英文别名: 5-chloro-3-diphenylphosphoryl-1H-indole-2-carboxamide
• 化学式: C₂₁H₁₆ClN₂O₂P
• 分子量: 394.797
• InChiKey: ATWQGXCSWDKEMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl 5-chloro-1-phenylsulfonyl-1H-indole-2-carboxylate 在 正丁基锂 、 氨 、 溴 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-chloro-3-(diphenylphosphinyl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Aryl-phospho-indole as Novel HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  A novel series of 3-aryl-phospho-indole (API) non-nucleoside reverse transcriptase inhibitors of HIV-1 was developed Chemical variation in the phosphorus linker led to the discovery of 3-phenyl-methyl-phosphinate-2-carboxamide 14, which possessed excellent potency against wild-type HIV-1 as well as viruses bearing K103N and Y181C single mutants in the reverse transcriptase gene Chiral separation of the enantiomers showed that only R enantiomer retained the activity The pharmacokinetic, solubility, and metabolic properties of 14 were assessed

  DOI：

  10.1021/jm101142k

文献信息

• PHOSPHO-INDOLES AS HIV INHIBITORS
  申请人：Storer Richard

  公开号：US20090163444A1

  公开（公告）日：2009-06-25

  3-phosphoindole compounds for the treatment of retroviral infections, and particularly for HIV, are described. Also included are compositions comprising the 3-phosphoindole derivatives alone or in combination with one or more other anti-retroviral agents, processes for their preparation, and methods of manufacturing a medicament incorporating these compounds.

  本文介绍了用于治疗逆转录病毒感染，尤其是HIV的3-磷酸吲哚化合物。还包括仅由3-磷酸吲哚衍生物或与一种或多种其他抗逆转录病毒药物组合而成的组合物，其制备过程以及制造包含这些化合物的药物的方法。
• Phosphoindoles as HIV inhibitors
  申请人：IDENIX Pharmaceuticals, Inc.

  公开号：EP1961757A1

  公开（公告）日：2008-08-27

  3-phosphoindole compounds for the treatment of retroviral infections, and particularly for HIV, are described. Also included are compositions comprising the 3-phosphoindole derivatives alone or in combination with one or more other anti-retroviral agents, processes for their preparation, and methods of manufacturing a medicament incorporating these compounds.

  本文描述了用于治疗逆转录病毒感染，特别是艾滋病毒的 3-膦酰吲哚化合物。此外，还包括由 3-膦酰吲哚衍生物单独或与一种或多种其他抗逆转录病毒药物组合而成的组合物、其制备工艺以及制造含有这些化合物的药物的方法。
• Phospho-indoles as HIV inhibitors
  申请人：IDENIX Pharmaceuticals, Inc.

  公开号：EP2256124A1

  公开（公告）日：2010-12-01

  3-Phosphoindonle compounds for the treatment of retroviral infections, and particularly for HIV, are described. Also included are compositions comprising the 3-phosphoindole derivatives alone or in combination with one or more other anti-retroviral agents, processes for their preparation, and methods of manufacturing a medicament incorporating these compounds.

  本文描述了用于治疗逆转录病毒感染，特别是艾滋病毒的 3-磷吲哚化合物。此外，还包括由 3-磷吲哚衍生物单独或与一种或多种其他抗逆转录病毒药物组合而成的组合物、其制备工艺以及生产含有这些化合物的药物的方法。
• US7534809B2
  申请人：——

  公开号：US7534809B2

  公开（公告）日：2009-05-19
• US8044091B2
  申请人：——

  公开号：US8044091B2

  公开（公告）日：2011-10-25