(2S,3S,5S)-1-(tert-butoxycarbonyl)-5-[(cyanomethyl)(ethyl)carbamoyl]-2-methyl-3-pyrrolidinecarboxylic acid | 1009735-91-4

• 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: (2S,3S,5S)-1-(tert-butoxycarbonyl)-5-[(cyanomethyl)(ethyl)carbamoyl]-2-methyl-3-pyrrolidinecarboxylic acid
• CAS: 1009735-91-4
• 化学式: C₁₆H₂₅N₃O₅
• 分子量: 339.392
• InChiKey: BMCKLIWLGCNDST-SRVKXCTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  110.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  异吲哚啉 、 (2S,3S,5S)-1-(tert-butoxycarbonyl)-5-[(cyanomethyl)(ethyl)carbamoyl]-2-methyl-3-pyrrolidinecarboxylic acid 在 1-羟基苯并三唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 tert-butyl (2S,3S,5S)-5-[(cyanomethyl)(ethyl)carbamoyl]-2-methyl-3-(1,3-dihydro-1H-isoindol-2-ylcarbonyl)-1-pyrrolidinecarboxylate
  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
• 作为产物：
  描述：

  3-benzyl 1-tert-butyl (2S,3S,5S)-5-[(cyanomethyl)(ethyl)carbamoyl]-2-methyl-1,3-pyrrolidinedicarboxylate 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 生成 (2S,3S,5S)-1-(tert-butoxycarbonyl)-5-[(cyanomethyl)(ethyl)carbamoyl]-2-methyl-3-pyrrolidinecarboxylic 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