(5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2-methyl-4,5-dihydro-1H-pyrrole-3-carboxylic acid | 918650-03-0

• 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: (5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2-methyl-4,5-dihydro-1H-pyrrole-3-carboxylic acid
• 英文别名: (2S)-2-methoxycarbonyl-5-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]-2,3-dihydropyrrole-4-carboxylic acid
• CAS: 918650-03-0
• 化学式: C₁₃H₁₉NO₆
• 分子量: 285.297
• InChiKey: HJITULIHJZQYKI-VIFPVBQESA-N

物化性质

• 沸点：
  391.0±42.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 (5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2-methyl-4,5-dihydro-1H-pyrrole-3-carboxylic 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99%的产率得到1-tert-butyl 2-methyl (2S)-5-methyl-4-[(4-methyl-1-piperazinyl)carbonyl]-2,3-dihydro-1H-pyrrole-1,2-dicarboxylate
  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：

  4-benzyl 1-tert-butyl 2-methyl (2S)-5-methyl-2,3-dihydro-1H-pyrrole-1,2,4-tricarboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以92%的产率得到(5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2-methyl-4,5-dihydro-1H-pyrrole-3-carboxylic acid
  参考文献：
  名称：

  Discovery of long-acting N-(cyanomethyl)-N-alkyl-l-prolinamide inhibitors of dipeptidyl peptidase IV

  摘要：

  Details of structure-activity relationships (SAR) for P2 moiety of a P1 2-cyanopyrrolidine dipeptidyl peptidase IV (DPP-IV) inhibitor 4a including stereochemistry are presented. Based on this information, a series of PI (N-alkyl)aminoacetonitrile analogs 9-20 possessing optimal P2 structure were synthesized and evaluated as inhibitors of DPP-IV. Among them, a representative compound 11, N-(cyanomethyl)-N-ethyl-L-prolinamide, was further evaluated to determine its effect on the plasma glucose level. Also 4a, 10, and 11 were evaluated for their isozyme selectivity to predict their safety problems. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.005