tert-butyl 4-[(2Z)-3-amino-2-butenethioyl]-1-piperazinecarboxylate | 1019637-71-8

• 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: tert-butyl 4-[(2Z)-3-amino-2-butenethioyl]-1-piperazinecarboxylate
• CAS: 1019637-71-8
• 化学式: C₁₃H₂₃N₃O₂S
• 分子量: 285.411
• InChiKey: GZFJPDHAXZMSQY-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  58.8
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-[(2Z)-3-amino-2-butenethioyl]-1-piperazinecarboxylate 在 吡啶 、 碘 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以99 mg的产率得到tert-butyl 4-(3-methyl-5-isothiazolyl)-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
• 作为产物：
  描述：

  4-甲基-6-硫氧代-3,6-二氢-2H-1,3-噻嗪-2-酮 、 N-Boc-哌嗪 以 异丙醇 为溶剂， 反应 10.0h， 以288 mg的产率得到tert-butyl 4-[(2Z)-3-amino-2-butenethioyl]-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