(3S,5S)-1-(tert-butoxycarbonyl)-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinecarboxylic acid | 898273-28-4

• 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: (3S,5S)-1-(tert-butoxycarbonyl)-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinecarboxylic acid
• 英文别名: (3S,5S)-1-(tert-butoxycarbonyl)-5-(pyrrolidin-1-ylcarbonyl)-3-pyrrolidinecarboxylic acid
• CAS: 898273-28-4
• 化学式: C₁₅H₂₄N₂O₅
• 分子量: 312.366
• InChiKey: CFOLICBUNSWYTE-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  87.15
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,5S)-1-(tert-butoxycarbonyl)-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinecarboxylic acid 、 1-(2-methyl-1,3-thiazol-5-yl)piperazine monohydrochloride 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 以70%的产率得到tert-butyl (2S,4S)-4-{[4-(2-methyl-1,3-thiazol-5-yl)-1-piperazinyl]carbonyl}-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinecarboxylate
  参考文献：
  名称：

  Design and synthesis of DPP-IV inhibitors lacking the electrophilic nitrile group

  摘要：

  A series of (4 beta-substituted)-L-prolylpyrrolidine analogs lacking the electrophilic nitrile function were synthesized and their dipeptidyl peptidase IV (DPP-IV) inhibitory activity and duration of ex vivo activity were evaluated. Structural optimization of a N-(3-phenyl-1,2,4-thiadiazol-5-yl) piperazine analog 8, which was found by high-speed analog synthesis, was carried out to improve the potency and duration of action. A representative compound 26 was evaluated to assess its effect on the plasma glucose level after the oGTT (oral glucose tolerance test) in normal rats. Structure-activity relationships (SAR) are also presented. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.031
• 作为产物：
  描述：

  1-tert-butyl 3-ethyl (3S,5S)-5-(1-pyrrolidinylcarbonyl)-1,3-pyrrolidinedicarboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以66%的产率得到(3S,5S)-1-(tert-butoxycarbonyl)-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinecarboxylic acid
  参考文献：
  名称：

  Design and synthesis of DPP-IV inhibitors lacking the electrophilic nitrile group

  摘要：

  A series of (4 beta-substituted)-L-prolylpyrrolidine analogs lacking the electrophilic nitrile function were synthesized and their dipeptidyl peptidase IV (DPP-IV) inhibitory activity and duration of ex vivo activity were evaluated. Structural optimization of a N-(3-phenyl-1,2,4-thiadiazol-5-yl) piperazine analog 8, which was found by high-speed analog synthesis, was carried out to improve the potency and duration of action. A representative compound 26 was evaluated to assess its effect on the plasma glucose level after the oGTT (oral glucose tolerance test) in normal rats. Structure-activity relationships (SAR) are also presented. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.031

文献信息

• WO2006/73167
  申请人：——

  公开号：——

  公开（公告）日：——