tert-butyl (2S,4S)-4-{[4-(3-methyl-1,2,4-thiadiazol-5-yl)-1,4-diazepan-1-yl]carbonyl}-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinecarboxylate | 1019637-94-5

• 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: tert-butyl (2S,4S)-4-{[4-(3-methyl-1,2,4-thiadiazol-5-yl)-1,4-diazepan-1-yl]carbonyl}-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinecarboxylate
• CAS: 1019637-94-5
• 化学式: C₂₃H₃₆N₆O₄S
• 分子量: 492.643
• InChiKey: GSIPXGFNIGMVLP-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  99.18
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,4S)-4-{[4-(3-methyl-1,2,4-thiadiazol-5-yl)-1,4-diazepan-1-yl]carbonyl}-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinecarboxylate 在 盐酸 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 16.0h， 以90%的产率得到1-(3-methyl-1,2,4-thiadiazol-5-yl)-4-{[(3S,5S)-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinyl]carbonyl}-1,4-diazepane monohydrochloride
  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：

  (3S,5S)-1-(tert-butoxycarbonyl)-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinecarboxylic acid 、 1-(3-Methyl-1,2,4-thiadiazol-5-yl)-1,4-diazepane 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 17.0h， 生成 tert-butyl (2S,4S)-4-{[4-(3-methyl-1,2,4-thiadiazol-5-yl)-1,4-diazepan-1-yl]carbonyl}-2-(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