5-<5'-chloro-2'-(methylthio)phenyl>imidazolidine-2,4-dione | 120121-13-3

• 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'-(methylthio)phenyl>imidazolidine-2,4-dione
• 英文别名: 5-(5-Chloro-2-methylsulfanylphenyl)imidazolidine-2,4-dione
• CAS: 120121-13-3
• 化学式: C₁₀H₉ClN₂O₂S
• 分子量: 256.713
• InChiKey: VPFAZTYASVUBNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 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：
  83.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-<5'-chloro-2'-(methylthio)phenyl>imidazolidine-2,4-dione 在 potassium permanganate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.5h， 以84%的产率得到5-<5'-chloro-2'-(methylsulfonyl)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
• 作为产物：
  描述：

  5-氯-2-巯基苯甲酸 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 sodium methylate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 5-<5'-chloro-2'-(methylthio)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

• RIZZI, J. P.;SCHNUR, R. C.
  作者：RIZZI, J. P.、SCHNUR, R. C.

  DOI：——

  日期：——
• 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.