ethyl 5-amino-1-(2,4-dichlorophenyl)-4-ethyl-1H-pyrazole-3-carboxylate | 1345992-60-0

• 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 5-amino-1-(2,4-dichlorophenyl)-4-ethyl-1H-pyrazole-3-carboxylate
• 英文别名: Ethyl 5-amino-1-(2,4-dichlorophenyl)-4-ethylpyrazole-3-carboxylate
• CAS: 1345992-60-0
• 化学式: C₁₄H₁₅Cl₂N₃O₂
• 分子量: 328.198
• InChiKey: ZBGKZBHSUKMDKH-UHFFFAOYSA-N

物化性质

• 熔点：
  155-157 °C(Solvent: Ethanol)
• 沸点：
  494.4±45.0 °C(predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-amino-1-(2,4-dichlorophenyl)-4-ethyl-1H-pyrazole-3-carboxylate 在 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 17.0h， 生成 N-cyclohexyl-1-(2,4-dichlorophenyl)-4-ethyl-5-(1H-pyrrol-1-yl)-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：

  potassium 3-cyano-1-ethoxy-1-oxopent-2-en-2-olate 、 2,4-二氯苯肼盐酸盐 以 乙醇 为溶剂， 反应 5.0h， 以59%的产率得到ethyl 5-amino-1-(2,4-dichlorophenyl)-4-ethyl-1H-pyrazole-3-carboxylate
  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

文献信息

• 1-Aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamide: An effective scaffold for the design of either CB1 or CB2 receptor ligands
  作者：Francesco Piscitelli、Alessia Ligresti、Giuseppe La Regina、Valerio Gatti、Antonella Brizzi、Serena Pasquini、Marco Allarà、Mauro Antonio Maria Carai、Ettore Novellino、Giancarlo Colombo、Vincenzo Di Marzo、Federico Corelli、Romano Silvestri

  DOI：10.1016/j.ejmech.2011.09.037

  日期：2011.11

  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.