3-(4-chloro-phenyl)-3-hydroxy-pyrrolidine-1-carboxylic acid ethyl ester | 96431-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-(4-chloro-phenyl)-3-hydroxy-pyrrolidine-1-carboxylic acid ethyl ester
• 英文别名: 1-carbethoxy-3-hydroxy-3-(4'-chlorophenyl)pyrrolidine；1-Aethoxycarbonyl-3-hydroxy-3-<4-chlor-phenyl-pyrrolidin；1-Ethoxycarbonyl-3-hydroxy-3-(4-chlor-phenyl)-pyrrolidin；1-Carbethoxy-3-(p-chlorphenyl)-3-pyrrolidinol；Ethyl 3-(4-chlorophenyl)-3-hydroxypyrrolidine-1-carboxylate
• CAS: 96431-51-5
• 化学式: C₁₃H₁₆ClNO₃
• 分子量: 269.728
• InChiKey: RHMUGCCBSHJFRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-chloro-phenyl)-3-hydroxy-pyrrolidine-1-carboxylic acid ethyl ester 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以84.6%的产率得到3-(4-chlorophenyl)-3-hydroxypyrrolidine
  参考文献：
  名称：

  Haloperidol analogs

  摘要：

  氟哌啶酮类似物符合以下结构式：其中：R为H，或—(CH2)n—OH，n为0至2的整数，且A为杂环桥接基团，主要由碳和至少一个氮原子组成，有效地保持连接的基团之间的距离，使得化合物（1）无法代谢为BCPP+类似物，具有对D2受体亚型的亲和力15

  公开号：

  US20060052363A1
• 作为产物：
  描述：

  乙基3-羟基-1-吡咯烷羧酸酯 在 K₂Cr₂O₄ 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 3-(4-chloro-phenyl)-3-hydroxy-pyrrolidine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Evaluation of the eutomer of 4-{3-(4-chlorophenyl)-3-hydroxypyrrolidin-1-yl}-1-(4-fluorophenyl)butan-1-one, {(+)-SYA 09}, a pyrrolidine analog of haloperidol

  摘要：

  Enantionteric separation of the racemic 4-{3-(4-chlorophenyl)-3-hydroxypyrrolidin-1-yl}-1-(4-fluorophenyl)butan-1-one, a pyrrolidine analog of haloperidol, {(+/-)-SYA 09}, and subsequent binding studies revealed that most of the binding affinity at dopamine and serotonin receptors resides in the (+)-isomer {(+)-SYA 09} or the eutomer. Further pharmacological evaluation of the eutomer revealed that it has a higher affinity for the dopamine D4 (DAD4) receptor subtype (K-i = 3.6 nM) than for the DAD2 subtype (K-i = 51.1 nM) with a ratio of 14.2 (D2K(i)/D4K(i) ratio = 14.2). In an animal model of antipsychotic efficacy, the (+)-SYA 09 was efficacious with an ED50 value of 1.6 mg/kg, ip, and at twice this value, (+)-SYA 09 did not induce significant catalepsy in rats. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.057

文献信息

• Synthesis and evaluation of ligands for D2-like receptors: The role of common pharmacophoric groups
  作者：Donald M.N. Sikazwe、Nancy T. Nkansah、Ramazan Altundas、Xue Y. Zhu、Bryan L. Roth、Vincent Setola、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2008.12.054

  日期：2009.2

  Arylcycloalkylamines, such as phenyl piperidines and piperazines and their arylalkyl substituents, constitute pharmacophoric groups exemplified in several antipsychotic agents. A review of previous reports indicates that arylalkyl substituents can improve the potency and selectivity of the binding affinity at D-2-like receptors. In this paper, we explored the contributions of two key pharmacophoric groups, that is, 40-fluorobutyrophenones and 3-methyl-7-azaindoles, to the potency and selectivity of synthesized agents at D-2-like receptors. Preliminary observation of binding affinities indicates that there is little predictability of specific effects of the arylalkyl moieties but the composite structure is responsible for selectivity and potency at these receptors. Published by Elsevier Ltd.
• US7700587B2
  申请人：——

  公开号：US7700587B2

  公开（公告）日：2010-04-20