(2S,3R,4R)-3-carboxymethyl-4-(4-methylphenylthio)pyrrolidine-2-carboxylicacid | 960009-03-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R,4R)-3-carboxymethyl-4-(4-methylphenylthio)pyrrolidine-2-carboxylicacid
• 英文别名: PSPA-4；(2S,3R,4R)-3-(carboxymethyl)-4-(4-methylphenyl)sulfanylpyrrolidine-2-carboxylic acid
• CAS: 960009-03-4
• 化学式: C₁₄H₁₇NO₄S
• 分子量: 295.359
• InChiKey: PZXINKABDLUNFH-GVXVVHGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-二溴苯基二硫化物 在 盐酸 、 4-二甲氨基吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 氯化亚砜 、 三丁基膦 、 水 、 potassium acetate 、 potassium carbonate 、 三乙胺 、 三(邻甲基苯基)磷 、 sodium hydroxide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 三环己基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 54.85h， 生成 (2S,3R,4R)-3-carboxymethyl-4-(4-methylphenylthio)pyrrolidine-2-carboxylicacid
  参考文献：
  名称：

  Synthesis of an acromelic acid A analog-based 11C-labeled PET tracer for exploration of the site of action of acromelic acid A in allodynia induction

  摘要：

  A novel C-11-labeled PET (positron emission tomography) tracer, which was designed based on the (phenylthio) pyrrolidine derivative that can competitively block the acromelic acid A-induced allodynia, was synthesized. A protocol in which methylation by palladium-mediated coupling of the boronate derivative with [C-11]CH3I and deprotection of the protected amino acid moiety are successively performed in one-pot within 5 min was established for the synthesis of the tracer. The tracer is potentially useful as a tool to investigate the mode of action of acromelic acid A in the induction of allodynia. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.018

文献信息

• EP2058301
  申请人：——

  公开号：——

  公开（公告）日：——
• Pyrrolidine analogue for preventing neurogenic pain and method for production thereof
  申请人：Suzuki Masaaki

  公开号：US20090306407A1

  公开（公告）日：2009-12-10

  [Problems] To provide a pyrrolidine analogue having an inhibitory activity on the induction of allodynia, a method for producing the pyrrolidine analogue, and an agent for preventing a neurogenic pain. [Means for Solving the Problems] A pyrrolidine analogue which is a compound represented by the general formula (I) [wherein HOOC-φ represents an aromatic substituent having at least one carboxy group attached to the benzene ring] or a salt or ester of the compound. The compound has a potent inhibitory effect on the induction of allodynia.
• US7968733B2
  申请人：——

  公开号：US7968733B2

  公开（公告）日：2011-06-28
• Synthesis of an acromelic acid A analog-based 11C-labeled PET tracer for exploration of the site of action of acromelic acid A in allodynia induction
  作者：Masakatsu Kanazawa、Kyoji Furuta、Hisashi Doi、Tomoko Mori、Toshiaki Minami、Seiji Ito、Masaaki Suzuki

  DOI：10.1016/j.bmcl.2011.02.018

  日期：2011.4

  A novel C-11-labeled PET (positron emission tomography) tracer, which was designed based on the (phenylthio) pyrrolidine derivative that can competitively block the acromelic acid A-induced allodynia, was synthesized. A protocol in which methylation by palladium-mediated coupling of the boronate derivative with [C-11]CH3I and deprotection of the protected amino acid moiety are successively performed in one-pot within 5 min was established for the synthesis of the tracer. The tracer is potentially useful as a tool to investigate the mode of action of acromelic acid A in the induction of allodynia. (C) 2011 Elsevier Ltd. All rights reserved.