2-Phenylsulfinylmethyl-3-phenylthioindole | 143246-73-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-Phenylsulfinylmethyl-3-phenylthioindole
• 英文别名: 1H-Indole, 2-[(phenylsulfinyl)methyl]-3-(phenylthio)-；2-(benzenesulfinylmethyl)-3-phenylsulfanyl-1H-indole
• CAS: 143246-73-5
• 化学式: C₂₁H₁₇NOS₂
• 分子量: 363.504
• InChiKey: WEJMICDBYIOXOH-UHFFFAOYSA-N

物化性质

• 沸点：
  609.1±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  77.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Phenylsulfinylmethyl-3-phenylthioindole 在 magnesium monoperoxyphthalate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 3-(benzenesulfinyl)-2-(benzenesulfinylmethyl)-1H-indole
  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
• 作为产物：
  描述：

  吲哚-2-羧酸甲酯 在 lithium aluminium tetrahydride 、 三丁基膦 、 sodium hydride 、 magnesium monoperoxyphthalate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 2-Phenylsulfinylmethyl-3-phenylthioindole
  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

• Inhibitors of HIV reverse transcriptase
  申请人：Merck & Co., Inc.

  公开号：US05527819A1

  公开（公告）日：1996-06-18

  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.

  新型吲哚化合物抑制HIV逆转录酶，在预防或治疗HIV感染以及治疗艾滋病方面具有用途，无论是作为化合物、药学上可接受的盐、药物组成成分，还是与其他抗病毒药物、抗感染药物、免疫调节剂、抗生素或疫苗结合使用。还描述了治疗艾滋病和预防或治疗HIV感染的方法。
• HIV reverse transcriptase
  申请人：Merck & Co., Inc.

  公开号：US05124327A1

  公开（公告）日：1992-06-23

  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 or 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.

  新型吲哚化合物抑制HIV逆转录酶，在预防或治疗HIV感染以及治疗艾滋病方面具有用途，无论是作为化合物还是药物组成成分，无论是否与其他抗病毒药物、抗感染药物、免疫调节剂、抗生素或疫苗结合使用。还描述了治疗艾滋病的方法以及预防或治疗HIV感染的方法。
• Indoles as inhibitors of HIV reverse transcriptase
  申请人：MERCK & CO. INC.

  公开号：EP0530907A1

  公开（公告）日：1993-03-10

  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.

  新型吲哚类化合物可以抑制HIV逆转录酶，并且可用于预防或治疗HIV感染以及治疗艾滋病，无论是作为化合物、药学上可接受的盐、药物组成成分，还是与其他抗病毒药物、抗感染药物、免疫调节剂、抗生素或疫苗组合使用。还描述了治疗艾滋病和预防或治疗HIV感染的方法。
• INHIBITORS OF HIV REVERSE TRANSCRIPTASE
  申请人：MERCK & CO. INC.

  公开号：EP0686148A1

  公开（公告）日：1995-12-13
• EP0686148A4
  申请人：——

  公开号：EP0686148A4

  公开（公告）日：1996-02-07