methyl 1-benzyl-3-pyrrolidineacetate cyclohexylsulfamate | 95274-13-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 氨基磺酸衍生物
• 英文名称: methyl 1-benzyl-3-pyrrolidineacetate cyclohexylsulfamate
• 英文别名: Cyclohexylsulfamic acid;methyl 2-(1-benzylpyrrolidin-3-yl)acetate
• CAS: 95274-13-8
• 化学式: C₆H₁₃NO₃S*C₁₄H₁₉NO₂
• 分子量: 412.55
• InChiKey: MENJOFGTUGOLAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 1-benzyl-3-pyrrolidineacetate cyclohexylsulfamate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 50.0 ℃ 、413.68 kPa 条件下， 反应 1.0h， 以36%的产率得到methyl 3-pyrrolidineacetate cyclohexylsulfamate
  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：

  1-苄基-3-吡咯烷乙酸甲酯 、 环拉酸 生成 methyl 1-benzyl-3-pyrrolidineacetate cyclohexylsulfamate
  参考文献：
  名称：

  BONDINELL, W. E.;LAFFERTY, J. J.;ZIRKLE, C. L.

  摘要：

  DOI：