2-苯基硫代甲基-1H-吲哚 | 143232-23-9

• 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: 2-苯基硫代甲基-1H-吲哚
• 英文名称: 2-phenylthiomethyl-1H-indole
• 英文别名: 2-Phenylthiomethylindole；(Phenylthiomethyl)indol；2-(phenylsulfanylmethyl)-1H-indole
• CAS: 143232-23-9
• 化学式: C₁₅H₁₃NS
• 分子量: 239.341
• InChiKey: OZCXZQSCHLRTPE-UHFFFAOYSA-N

物化性质

• 熔点：
  88 °C
• 沸点：
  435.7±28.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-苯基硫代甲基-1H-吲哚 在 sodium hydride 、 magnesium monoperoxyphthalate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 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
• 作为产物：
  描述：

  吲哚-2-羧酸甲酯 在 lithium aluminium tetrahydride 、 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-苯基硫代甲基-1H-吲哚
  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

• Sulfur-Assisted and 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Catalyzed Cyclization of 2-Alkynylanilines for the Metal-Free Synthesis of Indole Derivatives
  作者：Hongwei Zhou、Da Zhu、Yanpeng Xing、Huafeng Huang

  DOI：10.1002/adsc.201000280

  日期：2010.9.10

  sulfur‐assisted and 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU)‐catalyzed cyclization of 2‐alkynylanilines for the metal‐free synthesis of indole derivatives is reported. As a result of the metal‐free process, the ready availability of the starting materials and the simple and convenient operation, the type of reaction presented here has potential utility in organic synthesis. A 10‐gram scale preparation may

  据报道，在无金属合成吲哚衍生物的条件下，有硫辅助的1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）催化的2-炔基苯胺的环化反应。由于采用了无金属工艺，易于获得的起始原料以及简单便捷的操作，因此此处介绍的反应类型在有机合成中具有潜在的实用性。10克规模的制剂可能证明其可用于环境友好的吲哚衍生物合成中。
• 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。
• Aryl and heteroaryl ethers as agents for the treatment of hypersensitive aliments
  申请人：USV PHARMACEUTICAL CORPORATION

  公开号：EP0200101A2

  公开（公告）日：1986-12-10

  The present invention is concerned with the therapeutic composition comprising as an active ingredient a compound of the formula: and salts thereof; wherein Ar and Ar, are independently phenyl, naphthyl or a nitrogen, oxygen, or sulfur heterocyclic ring; R,, R2 and R3 are independently H, lower alkyl, lower alkoxy, hydroxy, halo, trihalomethyl, hydroxy-lower alkyl, alkyl carboxy, carboxy, formyl, lower alkyl carbonyl, aryl, aryloxy, benzyloxy, lower alkylamino, diloweralkylamino, cyano, lower alkanoyloxy, carbamoyl, lower alkoxy-lower alkoxy, lower carbalkoxy-lower alkoxy, nitro, amino, tetrahydropyranylmethyl, tetrazole, tetrazole lower alkyl, formyl amino or lower alkanoylamino; R, is independently H, lower alkyl, lower alkoxy, hydroxy, halo, trihalomethyl, hydroxy-lower alkyl, alkyl carboxy, carboxy, formyl, lower alkyl carbonyl, aryl, aryloxy, benzyloxy, lower alkylamino, diloweralkylamino, cyano, lower alkanoyloxy, carbamoyl, lower alkoxy-lower alkoxy, lower carbalkoxy-lower alkoxy, nitro, amino, tetrahydropyranylmethyl, or tetrazole, or tetrazole lower alkyl or Rs; Rs is lower alkoxy, phenyl, OH, CO2R6cyclic or heterocyclic structures.

  本发明涉及治疗组合物，该组合物包含作为活性成分的式化合物： 及其盐类；其中 Ar和Ar，独立地是苯基、萘基或氮、氧或硫杂环； R、R2 和 R3 独立地为 H、低级烷基、低级烷氧基、羟基、卤代、三卤甲基、羟基-低级烷基、烷基羧基、羧基、甲酰基、低级烷基羰基、芳基、芳氧基、苄氧基、低级烷基氨基、稀低级烷基氨基、氰基、烷基羰基、芳基羰基、芳氧基、苄氧基、低级烷基酰胺、稀低级烷基酰胺、低级烷基羰基下烷基羰基、芳基、芳氧基、苄氧基、下烷基氨基、稀烷基氨基、氰基、下烷酰氧基、氨基甲酰基、下烷氧基-下烷氧基、下碳烷氧基-下烷氧基、硝基、氨基、四氢吡喃甲基、四唑、四唑下烷基、甲酰氨基或下烷基氨基； R，独立地为 H、低级烷基、低级烷氧基、羟基、卤代、三卤甲基、羟基-低级烷基、烷基羧基、羧基、甲酰基、低级烷基羰基、芳基、芳氧基、苄氧基、低级烷基氨基低级烷基羰基、芳基、芳氧基、苄氧基、低级烷基氨基、稀低级烷基氨基、氰基、低级烷酰氧基、氨基甲酰基、低级烷氧基-低级烷氧基、低级碳烷氧基-低级烷氧基、硝基、氨基、四氢吡喃甲基、或四唑、或四唑低级烷基或 Rs； Rs 是低级烷氧基、苯基、OH、CO2R6 环结构或杂环结构。