3-chlorobenzenesulfonyl isocyanate | 68984-05-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-chlorobenzenesulfonyl isocyanate
• 英文别名: 3-Chlorobenzene-1-sulfonyl isocyanate；3-chloro-N-(oxomethylidene)benzenesulfonamide
• CAS: 68984-05-4
• 化学式: C₇H₄ClNO₃S
• 分子量: 217.633
• InChiKey: BUFPYFZTTSMGCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chlorobenzenesulfonyl isocyanate 在 甲基安非他命 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 3-氯苯磺胺
  参考文献：
  名称：

  Arnswald, Martin; Neumann, Wilhelm P., Chemische Berichte, 1991, vol. 124, # 9, p. 1997 - 2000

  摘要：

  DOI：
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 Chloro-3-(trimethylstannyl)benzene 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 3-chlorobenzenesulfonyl isocyanate
  参考文献：
  名称：

  Tin for organic synthesis. 10. Unconventional regiospecific syntheses of aromatic carbonamides and thiocarbonamides by means of tin-mediated Friedel-Crafts reactions

  摘要：

  Friedel-Crafts reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N-tosylcarbonamides 3 via ipso substitution of the stannyl group. Thus, unconventionally substituted aromatic carbonamides can be obtained. The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N-(arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on both aromatic rings. The known ipso-specific substitutions of stannylarenes with 14 are extended to bi- and tricyclic arenes as well as to thiophenes 6 and 22. One stannyl group can serve as a leaving group for two aromatic systems, as shown with diaryldialkyltins 29. Also, stannylalkanes such as 27 react with 14 to afford alkylsulfonyl isocyanates and products of further reactions, such as 28. From the reactions of 1 with ethoxycarbonyl isothiocyanate (32), ortho- and meta-substituted aromatic thiocarbonamides 33 which are potential precursors for further syntheses, are accessible. The scope, limitations, and mechanism of these electrophilic substitutions are outlined.

  DOI：

  10.1021/jo00077a020

文献信息

• [EN] INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION<br/>[FR] INHIBITEURS DE RÉPLICATION DU VIRUS DE L'IMMUNODÉFICIENCE HUMAINE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015061518A1

  公开（公告）日：2015-04-30

  Compounds of Formula I with activity against HIV, including pharmaceutical compositions and methods for using these compounds in treating human immunodeficiency virus (HIV) infection, are set forth: Formula :(I)

  具有抗艾滋病毒活性的I类化合物，包括用于治疗人类免疫缺陷病毒（HIV）感染的药物组合物和使用这些化合物的方法，如下所示：Formula :(I)
• NMDA antagonists
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05606063A1

  公开（公告）日：1997-02-25

  The present invention is directed to a new class of 4-sulfanimide-quinoline derivatives and to their use as NMDA antagonists.

  本发明涉及一类新的4-磺胺基喹啉衍生物，以及它们作为NMDA拮抗剂的用途。
• INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160257645A1

  公开（公告）日：2016-09-08

  Compounds of Formula I with activity against HIV, including pharmaceutical compositions and methods for using these compounds in treating human immunodeficiency virus (HIV) infection, are set forth: Formula: (I)

  具有抗HIV活性的I式化合物，包括制药组合物和使用这些化合物治疗人类免疫缺陷病毒（HIV）感染的方法，如下所示：公式：（I）
• Inhibitors of human immunodeficiency virus replication
  申请人：VIIV HEALTHCARE UK (NO. 5) LIMITED

  公开号：US10035760B2

  公开（公告）日：2018-07-31

  Compounds of Formula I with activity against HIV, including pharmaceutical compositions and methods for using these compounds in treating human immunodeficiency virus (HIV) infection, are set forth:

  本文阐述了具有抗 HIV 活性的式 I 化合物，包括使用这些化合物治疗人类免疫缺陷病毒 （HIV）感染的药物组合物和方法：
• Substituted 3-(Phenylsulfonyl)-1-phenylimidazolidine-2,4-dione Derivatives as Novel Nonpeptide Inhibitors of Human Heart Chymase
  作者：Shinjiro Niwata、Harukazu Fukami、Motoo Sumida、Akiko Ito、Saki Kakutani、Masayuki Saitoh、Kenji Suzuki、Masahiro Imoto、Hiroshi Shibata、Seiichi Imajo、Yoshinobu Kiso、Takaharu Tanaka、Hiroshi Nakazato、Takafumi Ishihara、Shinji Takai、Daisuke Yamamoto、Naotaka Shiota、Mizuo Miyazaki、Hideki Okunishi、Akio Kinoshita、Hidenori Urata、Kikuo Arakawa

  DOI：10.1021/jm960793t

  日期：1997.7.1

  A series of 3-(phenylsulfonyl)-1-phenylimidazolidine-2,4-dione derivatives have been synthesized and evaluated for their ability to selectively inhibit human heart chymase. The structure-activity relationship studies on these compounds gave the following results. The 1-phenyl moiety participates in a hydrophobic interaction where an optimum size is required. At this position, 3,4-dimethylphenyl is the best moiety for inhibiting chymase and showed high selectivity compared with chymotrypsin and cathepsin G. A 3-phenylsulfonyl moiety substituted with hydrogen-bond accepters such as nitrile and methoxycarbonyl enhances its activity. Molecular-modeling studies on the interaction of 3-[(4-chlorophenyl)sulfonyl]-1-(4-chlorophenyl)imidazolidine-2,4-dione (29) with the active site of human heart chymase suggested that the 1-phenyl moiety interacts with the hydrophobic P-1 pocket, the 3-phenylsulfonyl moiety resides in the S-1'-S-2' subsites, and the 4-carbonyl of the imidazolidine ring and sulfonyl group interact with the oxyanion hole and the His-45 side chain of chymase, respectively. The complex model is consistent with the structure-activity relationships.