methyl N-(4,4-diphenyl-3-butenyl)-3-pyrrolidineacetate | 95273-96-4

• 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: methyl N-(4,4-diphenyl-3-butenyl)-3-pyrrolidineacetate
• 英文别名: methyl 1-(4,4-diphenyl-3-butenyl)-3-pyrrolidineacetate；methyl 2-[1-(4,4-diphenylbut-3-enyl)pyrrolidin-3-yl]acetate
• CAS: 95273-96-4
• 化学式: C₂₃H₂₇NO₂
• 分子量: 349.473
• InChiKey: WURGTUVBDYAPIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N-(4,4-diphenyl-3-butenyl)-3-pyrrolidineacetate 在 盐酸 作用下， 反应 16.0h， 以59%的产率得到1-(4,4-diphenyl-3-butenyl)-3-pyrrolidineacetic acid
  参考文献：
  名称：

  Orally Active and Potent Inhibitors of γ-Aminobutyric Acid Uptake

  摘要：

  3-Pyrrolidineacetic acid (1a), certain piperidinecarboxylic acids--i.e., 3-piperidinecarboxylic acid (2a), 1,2,5,6-tetrahydro-3-pyridinecarboxylic acid (3a), and cis-4-hydroxy-3-piperidinecarboxylic acid (4a)--cis-3-aminocyclohexanecarboxylic acid (5a, cis-3-ACHC), and gamma-aminobutyric acid (6a, GABA) itself are among the most potent inhibitors of [3H]GABA uptake by neurons and glia in vitro. These hydrophilic amino acids, however, do not readily enter the central nervous system in pharmacologically significant amounts following peripheral administration. We now report that N-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylic acid (2b) is a specific GABA-uptake inhibitor that is more potent, more lipophilic and, in limited testing, as selective as 2a. Similar results were obtained with the N-(4,4-diphenyl-3-butenyl) derivatives of 1a, 3a, and 4a. By contrast, N-(4,4-diphenyl-3-butenyl) derivatives of 5a and 6a were not more potent than the parent amino acids and appear to inhibit GABA uptake, at least in part, by a nonselective mechanism of action. The N-(4,4-diphenyl-3-butenyl)amino acids 1b-4b exhibit anticonvulsant activity in rodents following oral or intraperitoneal administration [Yunger, L.M.; et al. J. Pharmacol. Exp. Ther. 1984, 228, 109].

  DOI：

  10.1021/jm50001a020
• 作为产物：
  描述：

  (4-溴-1-苯基丁-1-烯基)苯 、 methyl 3-pyrrolidineacetate cyclohexylsulfamate 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 43.0h， 以46%的产率得到methyl N-(4,4-diphenyl-3-butenyl)-3-pyrrolidineacetate
  参考文献：
  名称：

  Orally Active and Potent Inhibitors of γ-Aminobutyric Acid Uptake

  摘要：

  3-Pyrrolidineacetic acid (1a), certain piperidinecarboxylic acids--i.e., 3-piperidinecarboxylic acid (2a), 1,2,5,6-tetrahydro-3-pyridinecarboxylic acid (3a), and cis-4-hydroxy-3-piperidinecarboxylic acid (4a)--cis-3-aminocyclohexanecarboxylic acid (5a, cis-3-ACHC), and gamma-aminobutyric acid (6a, GABA) itself are among the most potent inhibitors of [3H]GABA uptake by neurons and glia in vitro. These hydrophilic amino acids, however, do not readily enter the central nervous system in pharmacologically significant amounts following peripheral administration. We now report that N-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylic acid (2b) is a specific GABA-uptake inhibitor that is more potent, more lipophilic and, in limited testing, as selective as 2a. Similar results were obtained with the N-(4,4-diphenyl-3-butenyl) derivatives of 1a, 3a, and 4a. By contrast, N-(4,4-diphenyl-3-butenyl) derivatives of 5a and 6a were not more potent than the parent amino acids and appear to inhibit GABA uptake, at least in part, by a nonselective mechanism of action. The N-(4,4-diphenyl-3-butenyl)amino acids 1b-4b exhibit anticonvulsant activity in rodents following oral or intraperitoneal administration [Yunger, L.M.; et al. J. Pharmacol. Exp. Ther. 1984, 228, 109].

  DOI：

  10.1021/jm50001a020

文献信息

• N-Substituted pyrrolidineacetic acids and their esters
  申请人：Smithkline Beckman Corporation

  公开号：US04514414A1

  公开（公告）日：1985-04-30

  N-Substituted pyrrolidineacetic acids and their esters, useful as inhibitors of GABA uptake, are prepared by reacting an appropriate N-alkylating derivative with an esters of an N-unsubstituted pyrrolidineacetic acid followed by hydrolysis of the ester.

  N-取代吡咯烷乙酸及其酯类，可用作GABA摄取抑制剂，制备方法为将适当的N-烷基化衍生物与N-未取代吡咯烷乙酸酯反应，然后水解酯。
• BONDINELL, W. E.;LAFFERTY, J. J.;ZIRKLE, C. L.
  作者：BONDINELL, W. E.、LAFFERTY, J. J.、ZIRKLE, C. L.

  DOI：——

  日期：——
• US4514414A
  申请人：——

  公开号：US4514414A

  公开（公告）日：1985-04-30