5-(4-chlorophenyl)-N-(2-cyanopropan-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide | 1265634-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)-N-(2-cyanopropan-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide
• CAS: 1265634-36-3
• 化学式: C₂₁H₁₇Cl₃N₄O
• 分子量: 447.751
• InChiKey: KULQULHEKHZXAV-UHFFFAOYSA-N

物化性质

• 沸点：
  595.8±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  70.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-N-(2-cyanopropan-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 在 ammonium hydroxide 、 硫化氢 作用下， 以 乙醇 、 水 为溶剂， 以80%的产率得到N-(1-amino-2-methyl-1-thioxopropan-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-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：

  1-(2,4-二氯苯基)-5-对氯苯基-4-甲基-吡唑-3-甲酸 、 N-氰基-N'-甲基乙脒 在 1-羟基苯并三唑 、 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 10.0h， 生成 5-(4-chlorophenyl)-N-(2-cyanopropan-2-yl)-1-(2,4-dichlorophenyl)-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

文献信息

• Novel pyrazole-3-carboxamide derivatives as cannabinoid-1 (CB1) antagonists: Journey from non-polar to polar amides
  作者：Pradip K. Sasmal、D. Srinivasa Reddy、Rashmi Talwar、B. Venkatesham、D. Balasubrahmanyam、M. Kannan、P. Srinivas、K. Shiva Kumar、B. Neelima Devi、Vikram P. Jadhav、Sanjoy K. Khan、Priya Mohan、Hira Chaudhury、Debnath Bhuniya、Javed Iqbal、Ranjan Chakrabarti

  DOI：10.1016/j.bmcl.2010.10.055

  日期：2011.1

  The synthesis and biological evaluation of novel pyrazole-3-carboxamide derivatives as CB1 antagonists are described. As a part of eastern amide SAR, various chemically diverse motifs were introduced. In general, a range of modifications were well tolerated. Several molecules with high polar surface area were also indentified as potent CB1 receptor antagonists. The in vivo proof of principle for weight loss is exemplified with a lead compound from this series. (C) 2010 Elsevier Ltd. All rights reserved.