1-(2-methyl-1,3-thiazol-5-yl)-4-{[(3S,5S)-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinyl]carbonyl}piperazine monohydrochloride | 898274-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(2-methyl-1,3-thiazol-5-yl)-4-{[(3S,5S)-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinyl]carbonyl}piperazine monohydrochloride
• 英文别名: 1-(2-methyl-1,3-thiazol-5-yl)-4-{[(3S,5S)-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinyl]carbonyl}piperazine hydrochloride
• CAS: 898274-98-1
• 化学式: C₁₈H₂₇N₅O₂S*ClH
• 分子量: 413.972
• InChiKey: VOHRFKIQPXGTRC-YYLIZZNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  68.78
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  tert-butyl (2S,4S)-4-{[4-(2-methyl-1,3-thiazol-5-yl)-1-piperazinyl]carbonyl}-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinecarboxylate 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 16.0h， 以57%的产率得到1-(2-methyl-1,3-thiazol-5-yl)-4-{[(3S,5S)-5-(1-pyrrolidinylcarbonyl)-3-pyrrolidinyl]carbonyl}piperazine 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