[(2R)-2-氨基-5-氧代-1-吡咯烷基]乙酸 | 150024-59-2

• 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
• 中文名称: [(2R)-2-氨基-5-氧代-1-吡咯烷基]乙酸
• 英文名称: [(2R)-2-Amino-5-oxopyrrolidin-1-yl]acetic acid
• 英文别名: 2-[(2R)-2-amino-5-oxopyrrolidin-1-yl]acetic acid
• CAS: 150024-59-2
• 化学式: C₆H₁₀N₂O₃
• 分子量: 158.157
• InChiKey: KHVKXWZYVMHZAC-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-(2-amino-5-oxo-pyrrolidin-1-yl)-acetic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(2R)-2-氨基-5-氧代-1-吡咯烷基]乙酸
  参考文献：
  名称：

  Synthesis and biological evaluation of novel dimiracetam derivatives useful for the treatment of neuropathic pain

  摘要：

  Chemical modifications of dimiracetam, a bicyclic analogue of the nootropic drug piracetam, afforded a small set of novel derivatives that were investigated in in vivo models of neuropathic pain. Compounds 5, 7 and 8 displayed a very promising antihyperalgesic profile in rat models of neuropathic pain induced by both chronic constriction injury of the sciatic nerve and streptozotocin. The compounds completely reverted the reduction of pain threshold evaluated by the paw pressure test. Importantly these derivatives did not induce any behavioural impairment as evaluated by the rotarod test. These results suggest that compounds 5, 7 and 8 might represent novel and well-tolerated therapeutic agents for the relief of neuropathic pain. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.015

文献信息

• PROCESS FOR THE PREPARATION OF CONDENSED IMIDAZOLES
  申请人：SMITHKLINE BEECHAM FARMACEUTICI S.p.A.

  公开号：EP0611371A1

  公开（公告）日：1994-08-24
• [EN] PROCESS FOR THE PREPARATION OF CONDENSED IMIDAZOLES
  申请人：SMITHKLINE BEECHAM FARMACEUTICI S.P.A.

  公开号：WO1993009120A1

  公开（公告）日：1993-05-13

  (EN) A process for the preparation of compounds of formula (I), wherein R1 represents hydrogen, C1-4 alkyl, CHR3CONHR4 or CHR3COOR4 in which R3 and R4 each independently represent hydrogen or C1-4alkyl; R2 represents hydrogen or C1-5 alkyl; and n is an integer 2, 3 or 4; which process comprises cyclising a compound of formula (II), wherein R2 and n are as defined in relation to formula (I); R5 represents hydrogen or a group COOR7 wherein R7 is a C1-4 alkyl group or a benzyl group; and R6 represents a hydroxy group or a group OR8 wherein R8 represents C1-6 alkyl or a benzyl group; and thereafter, as necessary, carrying out one more of the following steps: i) removing any protecting group; and ii) converting a compound of formula (I) into another compound of formula (I).(FR) Un procédé concerne la préparation de composés de formule (I) où R' représente hydrogène, C1-4 alkyle, CHR3CONHR4 ou CHR3COOR4 où R3 et R4 représentent chacun indépendamment hydrogène ou C1-4 alkyle; R2 représente hydrogène ou C1-5 alkyle; et n est un nombre entier de 2 à 4; le procédé implique de rendre cyclique un composé de formule (II) où R2 et n correspondent à la définition de la formule (I); R5 représente hydrogène ou un groupe COOR7 où R7 représente un groupe C1-4 alkyle ou un groupe benzyle ; et R6 représente un groupe hydroxy ou un groupe OR8 où R8 représente C1-6 alkyle ou un groupe benzyle; il convient par la suite d'effectuer une ou plusieurs des opérations suivantes: i) retirer tout groupe de protection et ii) transformer un composé de formule (I) en un autre composé de formule (I).
• Synthesis and biological evaluation of novel dimiracetam derivatives useful for the treatment of neuropathic pain
  作者：Carlo Farina、Stefania Gagliardi、Carla Ghelardini、Marisa Martinelli、Monica Norcini、Carlo Parini、Paola Petrillo、Silvano Ronzoni

  DOI：10.1016/j.bmc.2007.12.015

  日期：2008.3.15

  Chemical modifications of dimiracetam, a bicyclic analogue of the nootropic drug piracetam, afforded a small set of novel derivatives that were investigated in in vivo models of neuropathic pain. Compounds 5, 7 and 8 displayed a very promising antihyperalgesic profile in rat models of neuropathic pain induced by both chronic constriction injury of the sciatic nerve and streptozotocin. The compounds completely reverted the reduction of pain threshold evaluated by the paw pressure test. Importantly these derivatives did not induce any behavioural impairment as evaluated by the rotarod test. These results suggest that compounds 5, 7 and 8 might represent novel and well-tolerated therapeutic agents for the relief of neuropathic pain. (C) 2007 Elsevier Ltd. All rights reserved.