(R)-[3-{5-[(1H-benzimidazol-2-ylmethyl)carbamoyl]-4,5-dihydropyrazol-1-yl}-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester | 1078736-50-1

• 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: (R)-[3-{5-[(1H-benzimidazol-2-ylmethyl)carbamoyl]-4,5-dihydropyrazol-1-yl}-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester
• CAS: 1078736-50-1
• 化学式: C₂₇H₂₉F₃N₆O₄
• 分子量: 558.56
• InChiKey: VHUOAVSCUZGITM-XESZBRCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  128.78
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-[3-{5-[(1H-benzimidazol-2-ylmethyl)carbamoyl]-4,5-dihydropyrazol-1-yl}-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 12.0h， 以50%的产率得到2-[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-N-(1H-benzimidazol-2-ylmethyl)-3,4-dihydropyrazole-3-carboxamide;hydrochloride
  参考文献：
  名称：

  Synthesis and biological evaluation of pyrazoline analogues with β-amino acyl group as dipeptidyl peptidase IV inhibitors

  摘要：

  A series of pyrazoline derivatives with beta-amino acyl group were synthesized and evaluated for their ability to inhibit dipeptidyl peptidase IV. Several pyrazoline derivatives exhibited submicromolar inhibitory activities against DPP-IV. X-ray co-crystal structure of initial hit compound 1h was determined. Among this series, carboxylic acid substituted pyrazoline derivative 2u was the most active and greatly decreased the inhibitory activity toward CYP3A4 enzyme. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.11.029
• 作为产物：
  描述：

  (1H-苯并咪唑-2-亚甲基)胺 、 (R)-2-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyryl]-3,4-dihydro-2H-pyrazole-3-carboxylic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以28%的产率得到(R)-[3-{5-[(1H-benzimidazol-2-ylmethyl)carbamoyl]-4,5-dihydropyrazol-1-yl}-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of pyrazoline analogues with β-amino acyl group as dipeptidyl peptidase IV inhibitors

  摘要：

  A series of pyrazoline derivatives with beta-amino acyl group were synthesized and evaluated for their ability to inhibit dipeptidyl peptidase IV. Several pyrazoline derivatives exhibited submicromolar inhibitory activities against DPP-IV. X-ray co-crystal structure of initial hit compound 1h was determined. Among this series, carboxylic acid substituted pyrazoline derivative 2u was the most active and greatly decreased the inhibitory activity toward CYP3A4 enzyme. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.11.029