ethyl 5-chloro-1-phenylsulfonyl-1H-indole-2-carboxylate | 158561-88-7

• 物质功能分类: 有机原料 - 杂环化合物
• 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: ethyl 5-chloro-1-phenylsulfonyl-1H-indole-2-carboxylate
• 英文别名: 2-carboethoxy-5-chloro-1-phenylsulfonylindole；ethyl 5-chloro-1-(phenylsulfonyl)-1H-indole-2-carboxylate；ethyl 1-(benzenesulfonyl)-5-chloroindole-2-carboxylate
• CAS: 158561-88-7
• 化学式: C₁₇H₁₄ClNO₄S
• 分子量: 363.821
• InChiKey: VGGHSNNQLCWMCC-UHFFFAOYSA-N

物化性质

• 沸点：
  542.2±53.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 5-chloro-3-[(dimethylamino)phenylphosphinyl]-1H-indole-2-carboxamide
  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：

  5-氯吲哚-2-羧酸乙酯 、 苯磺酰氯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以90%的产率得到ethyl 5-chloro-1-phenylsulfonyl-1H-indole-2-carboxylate
  参考文献：
  名称：

  Phospho-indoles as HIV inhibitors

  摘要：

  描述了用于治疗逆转录病毒感染，特别是HIV的3-磷酸吲哚化合物。还包括仅含有3-磷酸吲哚衍生物或与一个或多个其他抗逆转录病毒药物组合的组合物，它们的制备过程，以及制造包含这些化合物的药物的方法。

  公开号：

  US20060074054A1

文献信息

• Phospho-indoles as HIV inhibitors
  申请人：Storer Richard

  公开号：US20060074054A1

  公开（公告）日：2006-04-06

  3-phosphoindole compounds for the treatment of retroviral infections, and particularly for HIV, are described. Also included are compositions comprising the 3-phosphoindole derivatives alone or in combination with one or more other anti-retroviral agents, processes for their preparation, and methods of manufacturing a medicament incorporating these compounds.

  描述了用于治疗逆转录病毒感染，特别是HIV的3-磷酸吲哚化合物。还包括仅含有3-磷酸吲哚衍生物或与一个或多个其他抗逆转录病毒药物组合的组合物，它们的制备过程，以及制造包含这些化合物的药物的方法。
• Combination therapy
  申请人：——

  公开号：US20040102360A1

  公开（公告）日：2004-05-27

  The present invention relates to methods of treating cancer using a combination of at least two Akt inhibitors or a compound which is an inhibitor of Akt and an inhibitor of a protein kinase, which methods comprise administering to a mammal, either sequentially in any order or simultaneously, amounts of at least two therapeutic agents selected from a group consisting of a compound(s) which are inhibitors of Akt and compound(s) which are inhibitors of protein kinases. The invention also relates to methods of preparing such compositions.

  本发明涉及使用至少两种Akt抑制剂的组合或一种同时是Akt抑制剂和蛋白激酶抑制剂的化合物来治疗癌症的方法，该方法包括向哺乳动物施用来自以下组合中选择的至少两种治疗剂的量，该组合包括Akt抑制剂和蛋白激酶抑制剂。该发明还涉及制备这种组合物的方法。
• 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。
• Tyrosine kinase inhibitors
  申请人：Dinsmore J. Christopher

  公开号：US20050261496A1

  公开（公告）日：2005-11-24

  The present invention relates to compounds that are capable of inhibiting, modulating and/or regulating signal transduction of both receptor-type and non-receptor type tyrosine kinases. The compounds of the instant invention possess a core structure that comprises a sulfonyl indole moiety. The present invention is also related to the pharmaceutically acceptable salts, hydrates and stereoisomers of these compounds.

  本发明涉及一种能够抑制、调节和/或调控受体型和非受体型酪氨酸激酶信号转导的化合物。本发明的化合物具有包含磺酰基吲哚基团的核心结构。本发明还涉及这些化合物的药学上可接受的盐、水合物和立体异构体。
• TYROSINE KINASE INHIBITORS
  申请人：Dinsmore Christopher J.

  公开号：US20100041652A1

  公开（公告）日：2010-02-18

  The present invention relates to compounds that are capable of inhibiting, modulating and/or regulating signal transduction of both receptor-type and non-receptor type tyrosine kinases. The compounds of the instant invention possess a core structure that comprises an indole-sulfonamide moiety. The present invention is also related to the pharmaceutically acceptable salts, hydrates and stereoisomers of these compounds.

  本发明涉及一种能够抑制、调节和/或调控受体型和非受体型酪氨酸激酶信号转导的化合物。本发明的化合物具有包含吲哚-磺酰胺基团的核心结构。本发明还涉及这些化合物的药学上可接受的盐、水合物和立体异构体。