5-Chloro-3-phenylsulfanyl-1H-indole-2-carboxylic acid methylamide

• 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-phenylsulfanyl-1H-indole-2-carboxylic acid methylamide
• 英文别名: 5-chloro-N-methyl-3-phenylsulfanyl-1H-indole-2-carboxamide
• 化学式: C₁₆H₁₃ClN₂OS
• 分子量: 316.811
• InChiKey: BEAHKSVMGOSPPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯吲哚-2-羧酸 在 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5-Chloro-3-phenylsulfanyl-1H-indole-2-carboxylic acid methylamide
  参考文献：
  名称：

  5-Chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase

  摘要：

  A series of highly potent, structurally novel, non-nucleoside RT inhibitors has been described. Low nanomolar concentrations of 5-chloro-3-(phenylsulfonyl)-indole-2-carboxamide (1) inhibit the HIV-1 RT enzyme in vitro and HTLVIIIb viral spread in MT-4 human T-lymphoid cells. Good oral bioavailability was observed in rhesus monkeys upon oral dosing of 1 as a suspension in methocel. When compared to other non-nucleoside inhibitors (e.g. 15-18), 1 possesses improved inhibitory potency with respect to the wild-type RT, as well as the K103N and Y181C mutant enzymes. Additional studies within this class of inhibitors are in progress.

  DOI：

  10.1021/jm00061a022

文献信息

• [EN] INDOLES AS INHIBITORS OF HIV REVERSE TRANSCRIPTASE
  申请人：MERCK & CO., INC.

  公开号：WO1993005020A1

  公开（公告）日：1993-03-18

  (EN) Novel indole compounds inhibit HIV reverse transcriptase, and are useful in the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, anti-infectives, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.(FR) De nouveaux composés indoles inhibent la transcriptase inverse du VIH et sont utiles dans la prévention ou le traitement d'infections par le VIH et le traitement du SIDA, soit en tant que composés, soit en tant que sels pharmaceutiquement acceptables, soit en tant qu'ingrédients de composition pharmaceutique, en combinaison ou non avec d'autres anti-viraux, anti-infectieux, immunomodulateurs, antibiotiques ou vaccins. Des méthodes de traitement du SIDA et des méthodes de prévention ou de traitement de l'infection par VIH sont également décrites.
• 5-Chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase
  作者：Theresa M. Williams、Terrence M. Ciccarone、Suzanne C. MacTough、Clarence S. Rooney、Suresh K. Balani、Jon H. Condra、Emilio A. Emini、Mark E. Goldman、William J. Greenlee

  DOI：10.1021/jm00061a022

  日期：1993.4

  A series of highly potent, structurally novel, non-nucleoside RT inhibitors has been described. Low nanomolar concentrations of 5-chloro-3-(phenylsulfonyl)-indole-2-carboxamide (1) inhibit the HIV-1 RT enzyme in vitro and HTLVIIIb viral spread in MT-4 human T-lymphoid cells. Good oral bioavailability was observed in rhesus monkeys upon oral dosing of 1 as a suspension in methocel. When compared to other non-nucleoside inhibitors (e.g. 15-18), 1 possesses improved inhibitory potency with respect to the wild-type RT, as well as the K103N and Y181C mutant enzymes. Additional studies within this class of inhibitors are in progress.