ethyl (R)-N-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylate hydrochloride | 95274-16-1

• 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: ethyl (R)-N-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylate hydrochloride
• CAS: 95274-16-1
• 化学式: C₂₄H₂₉NO₂*ClH
• 分子量: 399.961
• InChiKey: LVKLBCRRKMWAQD-VZYDHVRKSA-N

反应信息

• 作为反应物：
  描述：

  ethyl (R)-N-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylate hydrochloride 在 盐酸 作用下， 反应 17.0h， 以41%的产率得到(R)-N-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylic acid hydrochloride
  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