4-(2-吡咯烷)苯甲酸甲酯盐酸盐 | 1203685-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 4-(2-吡咯烷)苯甲酸甲酯盐酸盐
• 中文别名: 甲基4-(吡咯烷-2-基)苯甲酸酯盐酸盐
• 英文名称: methyl 4-(pyrrolidin-2-yl)benzoate hydrochloride
• 英文别名: methyl 4-pyrrolidin-2-ylbenzoate;hydrochloride
• CAS: 1203685-30-6
• 化学式: C₁₂H₁₅NO₂*ClH
• 分子量: 241.718
• InChiKey: HXDSVQMGMNSYNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-(2-吡咯烷)苯甲酸甲酯盐酸盐 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-羟基-7-氮杂苯并三氮唑 、 sodium hexamethyldisilazane 、 1,2-二氯乙烷 、 三乙胺 、 lithium hydroxide 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 57.0h， 生成 methyl 3-(4-(1-(4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)pyrrolidin-2-yl)benzamido)propanoate
  参考文献：
  名称：

  Identification of a novel conformationally constrained glucagon receptor antagonist

  摘要：

  Identification of orally active, small molecule antagonists of the glucagon receptor represents a novel treatment paradigm for the management of type 2 diabetes mellitus. The present work discloses novel glucagon receptor antagonists, identified via conformational constraint of current existing literature antagonists. Optimization of lipophilic ligand efficiency (LLE or LipE) culminated in enantiomers (+)-trans-26 and (-)-trans-27 which exhibit good physicochemical and in vitro drug metabolism profiles. In vivo, significant pharmacokinetic differences were noted with the two enantiomers, which were primarily driven through differences in clearance rates. Enantioselective oxidation by cytochrome P450 was ruled out as a causative factor for pharmacokinetic differences. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.090
• 作为产物：
  描述：

  tert-butyl 2-(4-(methoxycarbonyl)phenyl)-1H-pyrrole-1-carboxylate 在 盐酸 、 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 14.0h， 生成 4-(2-吡咯烷)苯甲酸甲酯盐酸盐
  参考文献：
  名称：

  Structure-Activity relationship of 1-(Furan-2ylmethyl)Pyrrolidine-Based Stimulation-2 (ST2) inhibitors for treating graft versus host disease

  摘要：

  DOI：

  10.1016/j.bmc.2022.116942

文献信息

• Identification of a novel conformationally constrained glucagon receptor antagonist
  作者：Esther C.Y. Lee、Meihua Tu、Benjamin D. Stevens、Jianwei Bian、Gary Aspnes、Christian Perreault、Matthew F. Sammons、Stephen W. Wright、John Litchfield、Amit S. Kalgutkar、Raman Sharma、Mary T. Didiuk、David C. Ebner、Kevin J. Filipski、Janice Brown、Karen Atkinson、Jeffrey A. Pfefferkorn、Angel Guzman-Perez

  DOI：10.1016/j.bmcl.2013.12.090

  日期：2014.2

  Identification of orally active, small molecule antagonists of the glucagon receptor represents a novel treatment paradigm for the management of type 2 diabetes mellitus. The present work discloses novel glucagon receptor antagonists, identified via conformational constraint of current existing literature antagonists. Optimization of lipophilic ligand efficiency (LLE or LipE) culminated in enantiomers (+)-trans-26 and (-)-trans-27 which exhibit good physicochemical and in vitro drug metabolism profiles. In vivo, significant pharmacokinetic differences were noted with the two enantiomers, which were primarily driven through differences in clearance rates. Enantioselective oxidation by cytochrome P450 was ruled out as a causative factor for pharmacokinetic differences. (C) 2014 Elsevier Ltd. All rights reserved.
• Structure-Activity relationship of 1-(Furan-2ylmethyl)Pyrrolidine-Based Stimulation-2 (ST2) inhibitors for treating graft versus host disease
  作者：Xinrui Yuan、Hua Jiang、Denggang Fu、Aaron Robida、Krishani Rajanayake、Hebao Yuan、Bo Wen、Duxin Sun、Brennan T. Watch、Krishnapriya Chinnaswamy、Jeanne A. Stuckey、Sophie Paczesny、Jason C. Rech、Chao-Yie Yang

  DOI：10.1016/j.bmc.2022.116942

  日期：2022.10