benzyl 4-{[(2S,3S,5S)-1-(tert-butoxycarbonyl)-2-methyl-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinyl]carbonyl}-1-piperazinecarboxylate | 1019638-25-5

• 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: benzyl 4-{[(2S,3S,5S)-1-(tert-butoxycarbonyl)-2-methyl-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinyl]carbonyl}-1-piperazinecarboxylate
• CAS: 1019638-25-5
• 化学式: C₂₈H₄₀N₄O₆
• 分子量: 528.649
• InChiKey: KKJVQMJPYZCXOD-PMVMPFDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  38.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  99.7
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl 4-{[(2S,3S,5S)-1-(tert-butoxycarbonyl)-2-methyl-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinyl]carbonyl}-1-piperazinecarboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以79%的产率得到tert-butyl (2S,3S,5S)-2-methyl-3-(1-piperazinylcarbonyl)-5-(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：

  四氢吡咯 、 (2S,4S,5S)-4-({4-[(benzyloxy)carbonyl]-1-piperazinyl}carbonyl)-1-(tert-butoxycarbonyl)-5-methyl-2-pyrrolidinecarboxylic acid 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45%的产率得到benzyl 4-{[(2S,3S,5S)-1-(tert-butoxycarbonyl)-2-methyl-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinyl]carbonyl}-1-piperazinecarboxylate
  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