methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenylthio)-3-(tert-butoxycarbonylmethyl)pyrrolidine-2-carboxylate | 960009-08-9

• 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: methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenylthio)-3-(tert-butoxycarbonylmethyl)pyrrolidine-2-carboxylate
• 英文别名: methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenyl)sulfanyl-3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]pyrrolidine-2-carboxylate
• CAS: 960009-08-9
• 化学式: C₂₅H₂₈BrNO₅S
• 分子量: 534.471
• InChiKey: LGHFOURUAPUEHY-ONTIZHBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenylthio)-3-(tert-butoxycarbonylmethyl)pyrrolidine-2-carboxylate 在 盐酸 、 水 作用下， 反应 21.5h， 生成 (2S,3R,4R)-4-((4-bromophenyl)thio)-3-(carboxymethyl)pyrrolidine-2-carboxylic acid hydrochloride
  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
• 作为产物：
  描述：

  4-二溴苯基二硫化物 、 (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester 在 三丁基膦 作用下， 以 甲苯 为溶剂， 反应 3.75h， 以96%的产率得到methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenylthio)-3-(tert-butoxycarbonylmethyl)pyrrolidine-2-carboxylate
  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.