2,2,2-trichloroethyl 4-{[(2S,3S,5S)-1-(tert-butoxycarbonyl)-2-methyl-5-(1,3-thiazolidin-3-ylcarbonyl)-3-pyrrolidinyl]carbonyl}-1-piperazinecarboxylate | 1019638-28-8

• 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: 2,2,2-trichloroethyl 4-{[(2S,3S,5S)-1-(tert-butoxycarbonyl)-2-methyl-5-(1,3-thiazolidin-3-ylcarbonyl)-3-pyrrolidinyl]carbonyl}-1-piperazinecarboxylate
• CAS: 1019638-28-8
• 化学式: C₂₂H₃₃Cl₃N₄O₆S
• 分子量: 587.952
• InChiKey: ZSEZXLBBBPIIKK-JYJNAYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  36.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  99.7
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl 4-{[(2S,3S,5S)-1-(tert-butoxycarbonyl)-2-methyl-5-(1,3-thiazolidin-3-ylcarbonyl)-3-pyrrolidinyl]carbonyl}-1-piperazinecarboxylate 在 溶剂黄146 、 锌 作用下， 反应 15.0h， 以880 mg的产率得到tert-butyl (2S,3S,5S)-2-methyl-3-(1-piperazinylcarbonyl)-5-(1,3-thiazolidin-3-ylcarbonyl)-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：

  tert-butyl (2S,3S,5S)-2-methyl-3-[(4-methyl-1-piperazinyl)carbonyl]-5-(1,3-thiazolidin-3-ylcarbonyl)-1-pyrrolidinecarboxylate 、 氯甲酸-2,2,2-三氯乙酯 以 乙腈 为溶剂， 反应 2.0h， 以41%的产率得到2,2,2-trichloroethyl 4-{[(2S,3S,5S)-1-(tert-butoxycarbonyl)-2-methyl-5-(1,3-thiazolidin-3-ylcarbonyl)-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