5-(2-chloro-1H-pyrrol-1-yl)-1-(3,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid | 1345992-75-7

• 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-(2-chloro-1H-pyrrol-1-yl)-1-(3,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid
• CAS: 1345992-75-7
• 化学式: C₁₅H₁₀Cl₃N₃O₂
• 分子量: 370.622
• InChiKey: QNBSTYJJQGKJCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.05
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-(2-chloro-1H-pyrrol-1-yl)-1-(3,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid 、 3,4-二氯苄胺 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 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到5-(2-chloro-1H-pyrrol-1-yl)-N-(3,4-dichlorobenzyl)-1-(3,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  1-Aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamide: An effective scaffold for the design of either CB1 or CB2 receptor ligands

  摘要：

  New 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides were synthesized as cannabinoid (CB) receptor ligands. Compound 11 (CB1 K-i = 2.3 nM, CB1 SI = 163.6) showed CB1 receptor affinity and selectivity superior to Rimonabant and AM251. Acute administration of 2 mg/kg 11 reduced sucrose, but not regular food, intake in rats. On the other hand, compound 23 (CB2 K-i = 0.51 nM, CB2 SI =30.0) showed significant affinity and selectivity for the CB2 receptor. The results presented here show that the 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamide may serve as an effective scaffold for the design of either CB1 or CB2 receptor ligands. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.037
• 作为产物：
  描述：

  ethyl 5-amino-1-(3,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate 在 N-氯代丁二酰亚胺 、 溶剂黄146 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 5-(2-chloro-1H-pyrrol-1-yl)-1-(3,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  1-Aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamide: An effective scaffold for the design of either CB1 or CB2 receptor ligands

  摘要：

  New 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides were synthesized as cannabinoid (CB) receptor ligands. Compound 11 (CB1 K-i = 2.3 nM, CB1 SI = 163.6) showed CB1 receptor affinity and selectivity superior to Rimonabant and AM251. Acute administration of 2 mg/kg 11 reduced sucrose, but not regular food, intake in rats. On the other hand, compound 23 (CB2 K-i = 0.51 nM, CB2 SI =30.0) showed significant affinity and selectivity for the CB2 receptor. The results presented here show that the 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamide may serve as an effective scaffold for the design of either CB1 or CB2 receptor ligands. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.037