benzyl 4-[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-1,4-diazepane-1-carboxylate;hydrochloride | 1100226-69-4

• 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: benzyl 4-[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-1,4-diazepane-1-carboxylate;hydrochloride
• CAS: 1100226-69-4
• 化学式: C₂₃H₂₆F₃N₃O₃*ClH
• 分子量: 485.934
• InChiKey: XQVMZMBEHMLXLF-GMUIIQOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  75.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R)-benzyl 4-(3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoyl)-1,4-diazepine-1-carboxylate 在 盐酸 、 水 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 生成 benzyl 4-[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-1,4-diazepane-1-carboxylate;hydrochloride
  参考文献：
  名称：

  Synthesis and biological evaluation of homopiperazine derivatives with β-aminoacyl group as dipeptidyl peptidase IV inhibitors

  摘要：

  Compounds with homopiperazine skeleton are designed to find a potent DPP-IV inhibitor without inhibiting CYP. Thus a series of beta-aminoacyl-containing homopiperazine derivatives was synthesized and evaluated. Compounds with acid moiety were found to be potent inhibitors of DPP-IV without inhibiting CYP 3A4. More specifically, compound 7m showed nanomolar activity with no inhibition towards five subtypes of CYPs, was considered as a prototype for further derivatization. Based on its X-ray co-crystal structure with human DPP-IV, we identified compounds 7s and 7t which showed good in vitro activity, no CYP inhibition, and good selectivity.

  DOI：

  10.1016/j.bmcl.2008.10.076

文献信息

• Synthesis and biological evaluation of homopiperazine derivatives with β-aminoacyl group as dipeptidyl peptidase IV inhibitors
  作者：Jin Hee Ahn、Woul Seong Park、Mi Ae Jun、Mi Sik Shin、Seung Kyu Kang、Ki Young Kim、Sang Dal Rhee、Myung Ae Bae、Kwang Rok Kim、Sung Gyu Kim、Sun Young Kim、Sang Kwon Sohn、Nam Sook Kang、Jie Oh Lee、Duck Hyung Lee、Hyae Gyeong Cheon、Sung Soo Kim

  DOI：10.1016/j.bmcl.2008.10.076

  日期：2008.12

  Compounds with homopiperazine skeleton are designed to find a potent DPP-IV inhibitor without inhibiting CYP. Thus a series of beta-aminoacyl-containing homopiperazine derivatives was synthesized and evaluated. Compounds with acid moiety were found to be potent inhibitors of DPP-IV without inhibiting CYP 3A4. More specifically, compound 7m showed nanomolar activity with no inhibition towards five subtypes of CYPs, was considered as a prototype for further derivatization. Based on its X-ray co-crystal structure with human DPP-IV, we identified compounds 7s and 7t which showed good in vitro activity, no CYP inhibition, and good selectivity.