3-phenylthioindole-2-carboxamide | 148900-64-5

• 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: 3-phenylthioindole-2-carboxamide
• 英文别名: 1H-Indole-2-carboxamide, 3-(phenylthio)-；3-phenylsulfanyl-1H-indole-2-carboxamide
• CAS: 148900-64-5
• 化学式: C₁₅H₁₂N₂OS
• 分子量: 268.339
• InChiKey: FSWPMLRYVQIPLP-UHFFFAOYSA-N

物化性质

• 熔点：
  197 °C
• 沸点：
  530.8±35.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 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：
  84.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenylthioindole-2-carboxamide 以 四氢呋喃 为溶剂， 生成 2-Aminomethyl-3-phenylthioindole
  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：

  吲哚-2-羧酸乙酯 在 ammonium hydroxide 、 三氟化硼乙醚 、 氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-phenylthioindole-2-carboxamide
  参考文献：
  名称：

  Novel Indolyl Aryl Sulfones Active against HIV-1 Carrying NNRTI Resistance Mutations:  Synthesis and SAR Studies

  摘要：

  The potent anti-HIV-1 activities of L-737,126 (2) and PAS sulfones prompted us to design and test against HIV-1 in acutely infected MT-4 cells a number of novel 1- and 3-benzenesulfonylindoles. Indoles belonging to the 1-benzenesulfonyl series were found poorly or totally inactive. On the contrary, some of the 3-benzenesulfonyl derivatives turned out to be as potent as 2, being endowed with potencies in the low nanomolar concentration range. In particular, (2-methylphenyl)sulfonyl (72) and (3-methylphenyl)sulfonyl (73) derivatives showed EC50 values of 1 nM. Introduction of two methyl groups at positions 3 and 5 of the phenyl ring of 2 furnished derivatives (80 and 83) which showed very potent and selective anti-HIV-1 activity not only against the wt strain, but also against mutants carrying NNRTI-resistant mutations at positions 103 and 181 of the reverse transcriptase gene.

  DOI：

  10.1021/jm0211063

文献信息

• 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。
• 3-ARYLTHIOINDOLE-2-CARBOXAMIDE DERIVATIVES AND ANALOGS THEREOF AS INHIBITORS OF CASEIN KINASE I
  申请人：METZ Arthur William

  公开号：US20070142454A1

  公开（公告）日：2007-06-21

  The present invention relates to methods for treating a patient suffering from a disease or disorder of the central nervous system associated with the disturbance of the human circadian clock that are ameliorated by inhibition of casein kinase Iε activity such as, for example, mood disorders including major depressive disorder, bipolar I disorder and bipolar II disorder, and sleep disorders including circadian rhythm sleep disorders such as, for example, shift work sleep disorder, jet lag syndrome, advanced sleep phase syndrome and delayed sleep phase syndrome, comprising administering to said patient a therapeutically effective amount of a compound of formula I. its stereoisomer, enantiomer, racemate, tautomer or pharmaceutically acceptable salt thereof,

  本发明涉及一种治疗中枢神经系统疾病或障碍的方法，该疾病或障碍与人类昼夜节律紊乱有关，该方法通过抑制酪蛋白激酶Iε活性来改善，例如情绪障碍，包括重度抑郁障碍、双相I型障碍和双相II型障碍，以及睡眠障碍，包括昼夜节律睡眠障碍，例如轮班工作睡眠障碍、时差综合症、睡眠相位提前综合症和睡眠相位延后综合症，包括向该患者施用公式I化合物的治疗有效量，其立体异构体、对映异构体、外消旋体、互变异构体或其药学上可接受的盐。
• 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
• US5527819A
  申请人：——

  公开号：US5527819A

  公开（公告）日：1996-06-18