methyl 2-(aminocarbonyl)-5-chloro-1H-indol-3-yl-(phenyl)phosphinate | 1261065-13-7

• 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: methyl 2-(aminocarbonyl)-5-chloro-1H-indol-3-yl-(phenyl)phosphinate
• 英文别名: Methyl (R)-(2-carbamoyl-5-chloro-1H-indol-3-yl)phenylphosphinate；5-chloro-3-[methoxy(phenyl)phosphoryl]-1H-indole-2-carboxamide
• CAS: 1261065-13-7
• 化学式: C₁₆H₁₄ClN₂O₃P
• 分子量: 348.726
• InChiKey: NBMJEMWDMSGPCM-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  3

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 、 正己烷 、 二氧化碳 、 二乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 methyl 2-(aminocarbonyl)-5-chloro-1H-indol-3-yl-(phenyl)phosphinate 、 methyl 2-(aminocarbonyl)-5-chloro-1H-indol-3-yl-(phenyl)phosphinate
  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

• US8044091B2
  申请人：——

  公开号：US8044091B2

  公开（公告）日：2011-10-25
• Synthesis and Biological Evaluation of Aryl-phospho-indole as Novel HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors
  作者：François-René Alexandre、Agnès Amador、Stéphanie Bot、Catherine Caillet、Thierry Convard、Jocelyn Jakubik、Chiara Musiu、Barbara Poddesu、Luana Vargiu、Michel Liuzzi、Arlène Roland、Maria Seifer、David Standring、Richard Storer、Cyril B. Dousson

  DOI：10.1021/jm101142k

  日期：2011.1.13

  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