methyl 2-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamido)-2-methylpropanoate | 1331784-02-1

• 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: methyl 2-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamido)-2-methylpropanoate
• CAS: 1331784-02-1
• 化学式: C₂₂H₂₀Cl₃N₃O₃
• 分子量: 480.778
• InChiKey: ZJIUUQAAXYPXRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  73.22
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamido)-2-methylpropanoate 在 水 、 三乙胺 、 lithium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(1-(methoxy(methyl)amino)-2-methyl-1-oxopropan-2-yl)-4-methyl-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  Structure–activity relationship studies of novel pyrazole and imidazole carboxamides as cannabinoid-1 (CB1) antagonists

  摘要：

  The synthesis and biological evaluation of novel pyrazole and imidazole carboxamides as CB1 antagonists are described. As a part of eastern amide SAR, various chemically diverse motifs were introduced on rimonabant template. The central pyrazole core was also replaced with its conformationally constrained motif and imidazole moieties. In general, a range of modifications were well tolerated. Several molecules with low- and sub-nanomolar potencies were identified as potent CB1 receptor antagonists. The in vivo proof of principle for weight loss is demonstrated with a lead compound in DIO mice model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.017
• 作为产物：
  描述：

  2-氨基异丁酸甲酯盐酸盐 、 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以21.5 g的产率得到methyl 2-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamido)-2-methylpropanoate
  参考文献：
  名称：

  Structure–activity relationship studies of novel pyrazole and imidazole carboxamides as cannabinoid-1 (CB1) antagonists

  摘要：

  The synthesis and biological evaluation of novel pyrazole and imidazole carboxamides as CB1 antagonists are described. As a part of eastern amide SAR, various chemically diverse motifs were introduced on rimonabant template. The central pyrazole core was also replaced with its conformationally constrained motif and imidazole moieties. In general, a range of modifications were well tolerated. Several molecules with low- and sub-nanomolar potencies were identified as potent CB1 receptor antagonists. The in vivo proof of principle for weight loss is demonstrated with a lead compound in DIO mice model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.017