ethyl 2-(4-(1-(2,4-dichlorophenyl)-4-ethyl-3-((2-(1-methyl-1H-tetrazol-5-yl)propan-2-yl)carbamoyl)-1H-pyrazol-5-yl)phenoxy)acetate | 1331783-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(4-(1-(2,4-dichlorophenyl)-4-ethyl-3-((2-(1-methyl-1H-tetrazol-5-yl)propan-2-yl)carbamoyl)-1H-pyrazol-5-yl)phenoxy)acetate
• 英文别名: Ethyl 2-[4-[2-(2,4-dichlorophenyl)-4-ethyl-5-[2-(1-methyltetrazol-5-yl)propan-2-ylcarbamoyl]pyrazol-3-yl]phenoxy]acetate
• CAS: 1331783-64-2
• 化学式: C₂₇H₂₉Cl₂N₇O₄
• 分子量: 586.478
• InChiKey: HKOVLGWNWHBSBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-(1-(2,4-dichlorophenyl)-4-ethyl-3-((2-(1-methyl-1H-tetrazol-5-yl)propan-2-yl)carbamoyl)-1H-pyrazol-5-yl)phenoxy)acetate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以74%的产率得到2-(4-(1-(2,4-dichlorophenyl)-4-ethyl-3-((2-(1-methyl-1H-tetrazol-5-yl)propan-2-yl)carbamoyl)-1H-pyrazol-5-yl)phenoxy)acetic acid
  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：

  benzyl (2-(1-methyl-1H-tetrazol-5-yl)propan-2-yl)carbamate 在 20% palladium hydroxide on carbon 、 氢气 、 三溴化硼 、 potassium carbonate 、 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 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 ethyl 2-(4-(1-(2,4-dichlorophenyl)-4-ethyl-3-((2-(1-methyl-1H-tetrazol-5-yl)propan-2-yl)carbamoyl)-1H-pyrazol-5-yl)phenoxy)acetate
  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

• Structure–activity relationship studies of novel pyrazole and imidazole carboxamides as cannabinoid-1 (CB1) antagonists
  作者：Pradip K. Sasmal、Rashmi Talwar、J. Swetha、D. Balasubrahmanyam、B. Venkatesham、Khaji Abdul Rawoof、B. Neelima Devi、Vikram P. Jadhav、Sanjoy K. Khan、Priya Mohan、D. Srinivasa Reddy、Vijay Kumar Nyavanandi、Srinivas Nanduri、K. Shiva Kumar、M. Kannan、P. Srinivas、Prabhakar Nadipalli、Hira Chaudhury、V.J. Sebastian

  DOI：10.1016/j.bmcl.2011.06.017

  日期：2011.8

  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.