3-cyanobenzenesulfonyl isocyanate

• 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-cyanobenzenesulfonyl isocyanate
• 英文别名: 3-cyanobenzenesulfonylisocyanate；3-cyano-N-(oxomethylidene)benzenesulfonamide
• 化学式: C₈H₄N₂O₃S
• 分子量: 208.197
• InChiKey: VLYUWILZJHOKQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 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：
  95.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-cyanobenzenesulfonyl isocyanate 在 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 3-(2,5-Dioxo-3-phenyl-imidazolidine-1-sulfonyl)-benzonitrile
  参考文献：
  名称：

  Substituted 3-(Phenylsulfonyl)-1-phenylimidazolidine-2,4-dione Derivatives as Novel Nonpeptide Inhibitors of Human Heart Chymase

  摘要：

  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.

  DOI：

  10.1021/jm960793t

文献信息

• Quinazoline derivatives and applications thereof
  申请人：Suntory Limited

  公开号：US05814631A1

  公开（公告）日：1998-09-29

  A chymase inhibitor containing as its effective ingredient a quinazoline derivative, or a pharmaceutically acceptable salt thereof, having the formula (1): ##STR1## and a pharmaceutical preparation for the prevention of cardiac and circulatory system diseases derived from abnormal exacerbation of Ang II production containing the same as its effective ingredient.

  一种含有喹唑啉衍生物作为有效成分的钳酶抑制剂，或其药用盐，其化学式为(1)：##STR1##以及一种以相同物质作为有效成分的用于预防由Ang II产生异常加剧引起的心脏和循环系统疾病的药物制剂。
• QUINAZOLINE DERIVATIVES AND USE THEREOF
  申请人：SUNTORY LIMITED

  公开号：EP0795548A1

  公开（公告）日：1997-09-17

  A chymase inhibitor containing as its effective ingredient a quinazoline derivative, or a pharmaceutically acceptable salt thereof, having the formula (1): and a pharmaceutical preparation for the prevention of cardiac and circulatory system diseases derived from abnormal exacerbation of Ang II production containing the same as its effective ingredient.

  一种糜蛋白酶抑制剂，其有效成分含有式（1）的喹唑啉衍生物或其药学上可接受的盐： 以及一种用于预防因血管紧张素 II 生成异常增加而引起的心脏和循环系统疾病的药物制剂，其有效成分也包含上述成分。
• IMIDAZOLIDINE DERIVATIVE AND USE THEREOF
  申请人：SUNTORY LIMITED

  公开号：EP0721944B1

  公开（公告）日：2001-01-17
• US5691335A
  申请人：——

  公开号：US5691335A

  公开（公告）日：1997-11-25
• US5814631A
  申请人：——

  公开号：US5814631A

  公开（公告）日：1998-09-29