benzyl 2-(aminocarbonyl)-5-chloro-1H-indol-3-yl-(phenyl)phosphinate | 1261065-12-6

• 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: benzyl 2-(aminocarbonyl)-5-chloro-1H-indol-3-yl-(phenyl)phosphinate
• 英文别名: 5-chloro-3-[phenyl(phenylmethoxy)phosphoryl]-1H-indole-2-carboxamide
• CAS: 1261065-12-6
• 化学式: C₂₂H₁₈ClN₂O₃P
• 分子量: 424.823
• InChiKey: IOFWZRKZJUBZKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 2-(aminocarbonyl)-5-chloro-1H-indol-3-yl-(phenyl)phosphinate 在 三甲基溴硅烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 以57%的产率得到[2-(aminocarbonyl)-5-chloro-1H-indol-3-yl]phenylphosphinic acid
  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
• 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 benzyl 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

• 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