5-<5'-chloro-2'-(methylsulfinyl)phenyl>imidazolidine-2,4-dione | 92539-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-<5'-chloro-2'-(methylsulfinyl)phenyl>imidazolidine-2,4-dione
• 英文别名: 5-(5-Chloro-2-Methylsulfinylphenyl)hydantoin；5-(5-Chloro-2-methylsulfinylphenyl)imidazolidine-2,4-dione
• CAS: 92539-55-4
• 化学式: C₁₀H₉ClN₂O₃S
• 分子量: 272.712
• InChiKey: XSWNTHJBWWYKHH-UHFFFAOYSA-N

物化性质

• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  94.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-<5'-chloro-2'-(methylthio)phenyl>imidazolidine-2,4-dione 在 sodium periodate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以37%的产率得到5-<5'-chloro-2'-(methylsulfinyl)phenyl>imidazolidine-2,4-dione
  参考文献：
  名称：

  Rotationally restricted mimics of rigid molecules: nonspirocyclic hydantoin aldose reductase inhibitors

  摘要：

  Sorbinil (1), a spirocyclic hydantoin, is a potent inhibitor of the enzyme aldose reductase. Simulation of the rigid spirocyclic ring orientation found in sorbinil was achieved with nonspirocyclic 5-[5'-chloro-2'-(alkylsulfonyl)-phenyl]hydantoins and 5-[5'-chloro-2'-[(N-alkylamino)sulfonyl]phenyl]hydantoins. The 2'-substituent (SO2R) was sufficiently large to hinder rotation of the hydantoin ring, forcing an orientation similar to that of a spirocyclic hydantoin. Calculated conformational preference, X-ray data, and inhibitory IC50 values for these nonspirocyclic 2'-substituted (SO2R) phenylhydantoins are in accord with what is expected for spirocyclic hydantoins and comparable to those of sorbinil.

  DOI：

  10.1021/jm00126a011

文献信息

• 5-(Substituted phenyl) hydantoins
  申请人：PFIZER INC.

  公开号：EP0112620A1

  公开（公告）日：1984-07-04

  A series of 5-(substituted phenyl)hydantoins and pharmaceutically acceptable salts thereof are aldose reductase inhibitors useful as agents for treatment of chronic diabetic complications, processes for preparing said compounds, and pharmaceutical compositions containing them.

  一系列 5-(取代苯基)海因及其药学上可接受的盐类是醛糖还原酶抑制剂，可作为治疗慢性糖尿病并发症的药物、制备上述化合物的工艺以及含有这些化合物的药物组合物。
• US4452806A
  申请人：——

  公开号：US4452806A

  公开（公告）日：1984-06-05
• Rotationally restricted mimics of rigid molecules: nonspirocyclic hydantoin aldose reductase inhibitors
  作者：James P. Rizzi、Rodney C. Schnur、Nancy J. Hutson、Kenneth G. Kraus、Paul R. Kelbaugh

  DOI：10.1021/jm00126a011

  日期：1989.6

  Sorbinil (1), a spirocyclic hydantoin, is a potent inhibitor of the enzyme aldose reductase. Simulation of the rigid spirocyclic ring orientation found in sorbinil was achieved with nonspirocyclic 5-[5'-chloro-2'-(alkylsulfonyl)-phenyl]hydantoins and 5-[5'-chloro-2'-[(N-alkylamino)sulfonyl]phenyl]hydantoins. The 2'-substituent (SO2R) was sufficiently large to hinder rotation of the hydantoin ring, forcing an orientation similar to that of a spirocyclic hydantoin. Calculated conformational preference, X-ray data, and inhibitory IC50 values for these nonspirocyclic 2'-substituted (SO2R) phenylhydantoins are in accord with what is expected for spirocyclic hydantoins and comparable to those of sorbinil.