1-Benzyl-5-oxo-pyrrolidine-2-carboxylic acid benzylamide | 247131-23-3

• 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: 1-Benzyl-5-oxo-pyrrolidine-2-carboxylic acid benzylamide
• 英文别名: N,1-dibenzyl-5-oxopyrrolidine-2-carboxamide
• CAS: 247131-23-3
• 化学式: C₁₉H₂₀N₂O₂
• 分子量: 308.38
• InChiKey: HYUOUXKRJPXXHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Benzyl-5-oxo-pyrrolidine-2-carboxylic acid benzylamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到N,1-dibenzylpyrrolidine-2-carboxamide
  参考文献：
  名称：

  Syntheses of 1,2-diamino and 1,2-aminoalcohol derivatives in the piperidine and pyrrolidine series as anti-amnesic agents

  摘要：

  Tacrine, one of the drugs available for Alzheimer's disease based on the cholinergic approach, suffers from considerable toxicity. Many analogues of tacrine has been prepared which retain the pharmacologically rich aminopyridine or aminoquinoline motifs. The current research is a continuation of our efforts in the area of 11-aminobenzoquinolizidines (4) and 10-aminobenzoindolizidines (5) (cf. ref 9). A serendipitous discovery led us to the biologically active open chain analogue 9, and we proceeded to elaborate on this molecule. Overall, the compounds we prepared were poor inhibitors of acetylcholinesterase as compared to tacrine. The single exception was compound 20 which exhibited an effect comparable to that of tacrine, but only at a dose in the order of 10(-3) M. However, despite the poor acetylcholinesterase inhibition by 9, this compound was found to be an effective antiamnesic agent. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00079-6
• 作为产物：
  描述：

  (S)-1-苄基-5-氧代吡咯烷-2-羧酸 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 1-Benzyl-5-oxo-pyrrolidine-2-carboxylic acid benzylamide
  参考文献：
  名称：

  Syntheses of 1,2-diamino and 1,2-aminoalcohol derivatives in the piperidine and pyrrolidine series as anti-amnesic agents

  摘要：

  Tacrine, one of the drugs available for Alzheimer's disease based on the cholinergic approach, suffers from considerable toxicity. Many analogues of tacrine has been prepared which retain the pharmacologically rich aminopyridine or aminoquinoline motifs. The current research is a continuation of our efforts in the area of 11-aminobenzoquinolizidines (4) and 10-aminobenzoindolizidines (5) (cf. ref 9). A serendipitous discovery led us to the biologically active open chain analogue 9, and we proceeded to elaborate on this molecule. Overall, the compounds we prepared were poor inhibitors of acetylcholinesterase as compared to tacrine. The single exception was compound 20 which exhibited an effect comparable to that of tacrine, but only at a dose in the order of 10(-3) M. However, despite the poor acetylcholinesterase inhibition by 9, this compound was found to be an effective antiamnesic agent. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00079-6

文献信息

• SUBSTITUTED NITROGEN HETEROCYCLIC COMPOUNDS AND THERAPEUTIC USES THEREOF
  申请人：AMERICAN BIOGENETIC SCIENCES, INC.

  公开号：EP1137412A2

  公开（公告）日：2001-10-04
• EP1137412A4
  申请人：——

  公开号：EP1137412A4

  公开（公告）日：2002-04-03
• [EN] SUBSTITUTED NITROGEN HETEROCYCLIC COMPOUNDS AND THERAPEUTIC USES THEREOF<br/>[FR] COMPOSES HETEROCYCLIQUES AZOTES SUBSTITUES ET LEUR UTILISATION THERAPEUTIQUE
  申请人：AMERICAN BIOGENETIC SCIENCES

  公开号：WO2000033788A2

  公开（公告）日：2000-06-15

  This invention relates to substituted nitrogen heterocyclic compounds having general formulas (1) and (2). This invention further relates to pharmaceutical compositions comprising these compounds, and therapeutic uses of such compositions for treating or controlling the symptoms of memory loss, Alzheimer's disease, senile dementia or similar conditions.
• Syntheses of 1,2-diamino and 1,2-aminoalcohol derivatives in the piperidine and pyrrolidine series as anti-amnesic agents
  作者：Shikai Zhao、Jeremiah P. Freeman、C.L. Bacon、G.B. Fox、E. O'Driscoll、A.G. Foley、J. Kelly、U. Farrell、Ciaran Regan、Stephen A. Mizsak、Jacob Szmuszkovicz

  DOI：10.1016/s0968-0896(99)00079-6

  日期：1999.8

  Tacrine, one of the drugs available for Alzheimer's disease based on the cholinergic approach, suffers from considerable toxicity. Many analogues of tacrine has been prepared which retain the pharmacologically rich aminopyridine or aminoquinoline motifs. The current research is a continuation of our efforts in the area of 11-aminobenzoquinolizidines (4) and 10-aminobenzoindolizidines (5) (cf. ref 9). A serendipitous discovery led us to the biologically active open chain analogue 9, and we proceeded to elaborate on this molecule. Overall, the compounds we prepared were poor inhibitors of acetylcholinesterase as compared to tacrine. The single exception was compound 20 which exhibited an effect comparable to that of tacrine, but only at a dose in the order of 10(-3) M. However, despite the poor acetylcholinesterase inhibition by 9, this compound was found to be an effective antiamnesic agent. (C) 1999 Elsevier Science Ltd. All rights reserved.