6-氯-1-(苯基磺酰基)-1H-吲哚-3-羧酰胺 | 148472-83-7

• 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
• 中文名称: 6-氯-1-(苯基磺酰基)-1H-吲哚-3-羧酰胺
• 英文名称: 5-chloro-3-(phenyl)sulfonyl-1H-indole-2-carboxamide
• 英文别名: 5-chloro-3-(phenylsulfonyl)indole-2-carboxamide；5-chloro-3-phenylsulfonylindole-2-carboxamide；RS1202；CSIC；5-chloro-3-(phenylsulfonyl)-1H-indole-2-carboxamide；3-Benzenesulfonyl-5-chloroindole-2-carboxamide；3-(benzenesulfonyl)-5-chloro-1H-indole-2-carboxamide
• CAS: 148472-83-7
• 化学式: C₁₅H₁₁ClN₂O₃S
• 分子量: 334.783
• InChiKey: KHJNUJLYIHQWQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-氯-1-(苯基磺酰基)-1H-吲哚-3-羧酰胺 生成 5-chloro-3-(phenylsulfonyl)-1H-indole-2-carbothioamide
  参考文献：
  名称：

  Inhibitors of HIV reverse transcriptase

  摘要：

  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。

  公开号：

  US05527819A1
• 作为产物：
  描述：

  5-氯-3-苯基硫基-1H-吲哚-2-甲酰胺 在 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 6.0h， 以84%的产率得到6-氯-1-(苯基磺酰基)-1H-吲哚-3-羧酰胺
  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

• Self-emulsifying drug delivery system
  申请人：G.D. Searle & Co.

  公开号：US20040048934A1

  公开（公告）日：2004-03-11

  Oral pharmaceutical formulation which improves the bioavailability of pharmaceuticals which are substantially water and oil insoluble is disclosed. In addition to the pharmaceutical, the formulation includes an emulsifier, an oil and an solubilizer. Alternatively, the formulation includes an aqueous solution of solubilizer.

  本发明揭示了一种口服制剂，可提高主要为水和油不溶性的药物的生物利用度。除了药物外，该制剂还包括乳化剂、油和溶剂。或者，该制剂包括溶剂水溶液。
• [EN] SUBSTITUTED INDOLES AND THEIR USE AS NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS<br/>[FR] INDOLES SUBSTITUÉS ET LEUR UTILISATION EN TANT QU'INHIBITEURS NON-NUCLÉOSIDIQUES DE LA TRANSCRIPTASE INVERSE
  申请人：UNIV STELLENBOSCH

  公开号：WO2015044928A1

  公开（公告）日：2015-04-02

  Compounds of Formula I or pharmaceutically acceptable salts thereof are claimed, wherein R1 is an ester, amide or a heterocycle; R2 is C or N; R3 is a methoxy or ethoxy group, an alkyl group or a heterocyclic group; R4 is a substituted or unsubstituted phenyl or heteroaromatic group; and R5 is a halide or a nitrile. The use of these compounds as non-nucleoside reverse transcriptase inhibitors (NNRTIs) for inhibiting or treating HIV infection or AIDS is also described.

  本发明涉及化合物I的配方或其药学上可接受的盐，其中R1是酯、酰胺或杂环；R2是C或N；R3是甲氧基或乙氧基基团、烷基或杂环基团；R4是取代或未取代的苯基或杂环芳基；R5是卤素或腈基。本发明还描述了这些化合物作为非核苷类逆转录酶抑制剂（NNRTIs）用于抑制或治疗HIV感染或艾滋病的用途。
• 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。
• [EN] SUBSTITUTED BENZIMIDAZOLES AS NON-NUCLEOSIDE INHIBITORS OF REVERSE TRANSCRIPTASE<br/>[FR] BENZIMIDAZOLES SUBSTITUES EN TANT QU'INHIBITEURS NON NUCLEOSIDIQUES DE LA TRANSCRIPTASE INVERSE
  申请人：US HEALTH

  公开号：WO2001014343A1

  公开（公告）日：2001-03-01

  Benzimidazole derivatives substituted in position 2 by a 2,6 difluorophenyl and/or in position 1 by a 2,6-difluorobenzyl group are HIV-1 reverse transcriptase inhibitors useful in treatment of HIV infections.

  2-位置被2,6-二氟苯基和/或1-位置被2,6-二氟苄基取代的苯并咪唑衍生物是HIV-1反转录酶抑制剂，可用于治疗HIV感染。
• Substituted benzimidazoles as non-nucleoside inhibitors of reverse transcriptase
  申请人：——

  公开号：US20030191160A1

  公开（公告）日：2003-10-09

  The present invention provides compositions and methods for the treatment of HIV infection. In particular, the present invention provides non-nucleoside inhibitors of reverse transcriptase (RT), as well as methods to treat HIV infection using these non-nucleoside inhibitors of RT. In preferred embodiments, the present invention provides a novel class of substituted benzimidazoles, effective in the inhibition of human immunodeficiency virus (HIV) RT.

  本发明提供了治疗HIV感染的组合物和方法。特别是，本发明提供了反转录酶（RT）非核苷类抑制剂，以及使用这些非核苷类RT抑制剂治疗HIV感染的方法。在优选实施例中，本发明提供了一类新型的取代苯并咪唑，能够有效抑制人类免疫缺陷病毒（HIV）RT。