1-[(4-chlorophenyl)sulfonyl]-2-(2-thienyl)pyrrolidine | 1193748-20-7

• 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: 1-[(4-chlorophenyl)sulfonyl]-2-(2-thienyl)pyrrolidine
• 英文别名: (2S)-1-(4-chlorophenyl)sulfonyl-2-thiophen-2-ylpyrrolidine
• CAS: 1193748-20-7
• 化学式: C₁₄H₁₄ClNO₂S₂
• mdl: MFCD02089612
• 分子量: 327.856
• InChiKey: WMCBPITWUUHVJB-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  CD 10415 在 Chiralpak-IA column 作用下， 以 正己烷 、 二氯甲烷 、 异丙醇 为溶剂， 生成 1-[(4-chlorophenyl)sulfonyl]-2-(2-thienyl)pyrrolidine 、 1-[(4-chlorophenyl)sulfonyl]-2-(2-thienyl)pyrrolidine
  参考文献：
  名称：

  Stereoselective Behavior of the Functional Diltiazem Analogue 1-[(4-Chlorophenyl)sulfonyl]-2-(2-thienyl)pyrrolidine, a New L-Type Calcium Channel Blocker

  摘要：

  We studied the stereoselective behavior of 1-[(4-chlorophenyl)sulfonyl]-2-(2-thienyl)pyrrolidine, a recently described blocker of cardiovascular L-type Calcium channels that binds to the diltiazem site. Given the stereocenter at C-2 of the pyrrolidine ring, the two enantiomers were separated by chiral HPLC and, using VCD in conjunction with DFT Calculations of chiroptical properties, the absolute configuration was assigned as R-(+)/S-(-). For both forms, functional, electrophysiological, and binding properties were studied and the three-dimensional superimpositions of the two enantiomers over diltiazem were obtained in silico. The significant differences observed for the two enantiomers well agreed with the experimental data, and molecular regions were hypothesized as responsible for the cardiac stereoselectivity and vascular stereospecifcity.

  DOI：

  10.1021/jm9008696

文献信息

• 1-ARENESULFONYL-2-ARYL-PYRROLIDINE AND PIPERIDINE DERIVATIVES FOR THE TREATMENT OF CNS DISORDERS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1165510B1

  公开（公告）日：2005-09-28
• US6284785B1
  申请人：——

  公开号：US6284785B1

  公开（公告）日：2001-09-04
• Stereoselective Behavior of the Functional Diltiazem Analogue 1-[(4-Chlorophenyl)sulfonyl]-2-(2-thienyl)pyrrolidine, a New L-Type Calcium Channel Blocker
  作者：Emanuele Carosati、Roberta Budriesi、Pierfranco Ioan、Gabriele Cruciani、Fabio Fusi、Maria Frosini、Simona Saponara、Francesco Gasparrini、Alessia Ciogli、Claudio Villani、Philip J. Stephens、Frank J. Devlin、Domenico Spinelli、Alberto Chiarini

  DOI：10.1021/jm9008696

  日期：2009.11.12

  We studied the stereoselective behavior of 1-[(4-chlorophenyl)sulfonyl]-2-(2-thienyl)pyrrolidine, a recently described blocker of cardiovascular L-type Calcium channels that binds to the diltiazem site. Given the stereocenter at C-2 of the pyrrolidine ring, the two enantiomers were separated by chiral HPLC and, using VCD in conjunction with DFT Calculations of chiroptical properties, the absolute configuration was assigned as R-(+)/S-(-). For both forms, functional, electrophysiological, and binding properties were studied and the three-dimensional superimpositions of the two enantiomers over diltiazem were obtained in silico. The significant differences observed for the two enantiomers well agreed with the experimental data, and molecular regions were hypothesized as responsible for the cardiac stereoselectivity and vascular stereospecifcity.