(2S)-1-(tert-butoxycarbonyl)-5-methyl-4-[(4-methyl-1-piperazinyl)carbonyl]-2,3-dihydro-1H-pyrrole-2-carboxylic acid | 1019638-20-0

• 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: (2S)-1-(tert-butoxycarbonyl)-5-methyl-4-[(4-methyl-1-piperazinyl)carbonyl]-2,3-dihydro-1H-pyrrole-2-carboxylic acid
• CAS: 1019638-20-0
• 化学式: C₁₇H₂₇N₃O₅
• 分子量: 353.418
• InChiKey: BZQUZFZNIXDGBV-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  90.39
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S)-1-(tert-butoxycarbonyl)-5-methyl-4-[(4-methyl-1-piperazinyl)carbonyl]-2,3-dihydro-1H-pyrrole-2-carboxylic acid 在 platinum(IV) oxide 氢气 、 溶剂黄146 作用下， 反应 29.0h， 以64%的产率得到(2S,4S,5S)-1-(tert-butoxycarbonyl)-5-methyl-4-[(4-methyl-1-piperazinyl)carbonyl]-2-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
• 作为产物：
  描述：

  1-tert-butyl 2-methyl (2S)-5-methyl-4-[(4-methyl-1-piperazinyl)carbonyl]-2,3-dihydro-1H-pyrrole-1,2-dicarboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以6.18 g的产率得到(2S)-1-(tert-butoxycarbonyl)-5-methyl-4-[(4-methyl-1-piperazinyl)carbonyl]-2,3-dihydro-1H-pyrrole-2-carboxylic 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