5-氯-3-苯基硫基-1H-吲哚-2-甲酰胺 | 148473-16-9

• 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: 5-氯-3-苯基硫基-1H-吲哚-2-甲酰胺
• 英文名称: 5-chloro-3-(phenylthio)-1H-indole-2-carboxamide
• 英文别名: 5-Chloro-3-phenylthioindole-2-carboxamide；5-chloro-3-phenylsulfanyl-1H-indole-2-carboxamide
• CAS: 148473-16-9
• 化学式: C₁₅H₁₁ClN₂OS
• 分子量: 302.784
• InChiKey: SEAXPFZOFZLHLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  212-213 °C
• 沸点：
  556.7±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 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：

  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
• 作为产物：
  描述：

  5-chloro-3-phenylthioindole-2-carboxylic acid 在 氨 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到5-氯-3-苯基硫基-1H-吲哚-2-甲酰胺
  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

• Iodine/Manganese Catalyzed Sulfenylation of Indole via Dehydrogenative Oxidative Coupling in Anisole
  作者：Weihe Li、Hao Wang、Shengping Liu、Hua Feng、Enrico Benassi、Bo Qian

  DOI：10.1002/adsc.202000291

  日期：2020.7.16

  This protocol describes an iodine/manganese catalytic system for dehydrogenative oxidative coupling reaction of indoles with thiols in anisole. Particularly, the dual roles of anisole have been first demonstrated as a solvent and as a promoter via the formation of an oxonium ion intermediate to accelerate the generation of products. A series of sulfenylindoles are readily constructed under aerobic

  该方案描述了碘/锰催化体系，用于吲哚中吲哚与硫醇的脱氢氧化偶联反应。特别是，苯甲醚的双重作用已首先通过形成氧离子中间体以加速产物的产生而证明其作为溶剂和促进剂。在需氧温和的反应条件下很容易构建一系列的亚磺酰基吲哚。此外，制备抗癌和抗艾滋病药物的成就证明了这种方法的实用性。机制研究揭示了可能的替代途径，并且单电子转移过程也参与了这一转变。
• 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。
• 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。
• DBU-Catalyzed Aerobic CDC Reaction of Thiophenols
  作者：Xuemin Jia、Xiao Ma、Wei Feng、Ji-Quan Zhang、Yonglong Zhao、Bing Guo、Lei Tang、Yuan-Yong Yang

  DOI：10.1021/acs.joc.2c02207

  日期：2022.12.16

  A convenient method was developed for the preparation of thiolated compounds via a DBU-catalyzed aerobic cross-dehydrogenative coupling (CDC) reaction. The established protocol is environmentally friendly and operationally simple. Substrates like (hetero)aryl acetates, (hetero)aryl ketones, and indoles could be transformed into the corresponding thiolated products in moderate to high yields and further

  通过DBU 催化的有氧交叉脱氢偶联 (CDC) 反应，开发了一种制备硫醇化化合物的简便方法。已建立的协议对环境友好且操作简单。(杂)芳基乙酸酯、(杂)芳基酮和吲哚等底物可以中高产率转化为相应的硫醇化产物，并以无预功能化的方式进一步应用于生物活性化合物的制备。