1-(2,4-dichlorophenyl)-5-(5-(3,3-dimethylbut-1-ynyl)thiophen-2-yl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester | 1058164-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2,4-dichlorophenyl)-5-(5-(3,3-dimethylbut-1-ynyl)thiophen-2-yl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester
• 英文别名: 1-(2,4-dichloro-phenyl)-5-[5-(3,3-dimethyl-but-1-ynyl)-thiophen-2-yl]-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester；ethyl 1-(2,4-dichlorophenyl)-5-[5-(3,3-dimethylbut-1-ynyl)thiophen-2-yl]-4-methylpyrazole-3-carboxylate
• CAS: 1058164-70-7
• 化学式: C₂₃H₂₂Cl₂N₂O₂S
• 分子量: 461.412
• InChiKey: SOHMDAVHZURTGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,4-dichlorophenyl)-5-(5-(3,3-dimethylbut-1-ynyl)thiophen-2-yl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester 生成 1-(2,4-dichlorophenyl)-5-(5-(3,3-dimethylbut-1-ynyl)thiophen-2-yl)-4-methyl-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  Oxadiazole Compounds

  摘要：

  一种具有以下化学式（I）的化合物：其中A、R1、R2和R3如本文所定义。还公开了（1）含有这种化合物的药物组合物，以及（2）使用这种化合物治疗大麻素受体介导的疾病的方法。

  公开号：

  US20080255211A1
• 作为产物：
  描述：

  5-(5-bromothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester 、 3,3-二甲基-1-丁炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 C.I.酸性橙108 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以94%的产率得到1-(2,4-dichlorophenyl)-5-(5-(3,3-dimethylbut-1-ynyl)thiophen-2-yl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Bioisosteric Replacement of the Pyrazole 5-Aryl Moiety of N-(Piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716A). A Novel Series of Alkynylthiophenes as Potent and Selective Cannabinoid-1 Receptor Antagonists

  摘要：

  Replacing the conventional pyrazole 5-aryl substituent of 1 (SR141716A) with the 2-thienyl rnoiety appended with ail appropriate alkynyl unit, a novel class of 5-(5-alkynyl-2-thienyl)pyrazole derivatives, behaving as highly potent CB1 receptor antagonists with good CB1/2 selectivity, was discovered, many of which, its typified by compound 18, showed significant weight reduction in diet-indUced obese Mouse model, thus pharmacologically validating that the bioisosteric replacement described above is viable. Also encouraging was the finding that a subtle structural modification of the newly developed series could result in a distinct difference in the intrinsic property, as demonstrated by compounds 12 (NA) and its methylated structural isomers 15 (PA) and 18 (IA). Moreover, current structure-activity relationship Studies revealed that around the pyrazole 5-position of 1, a deep and flat crevice surrounded by a sequence of hydrophobic/aromatic residues as indicated by the CB I-receptor homology model might exist in the binding site.

  DOI：

  10.1021/jm800066v

文献信息

• Oxadiazole compounds
  申请人：National Health Research Institutes

  公开号：US07705024B2

  公开（公告）日：2010-04-27

  A compound of formula (I): in which A, R1, R2, and R3 are as defined herein. Also disclosed are (1) a pharmaceutical composition containing such a compound, and (2) a method for treating a cannabinoid receptor-mediated disorder using such a compound.

  化合物式（I）如下： 其中A，R1，R2和R3的定义如本文所述。本文还披露了（1）含有这种化合物的药物组合物，以及（2）使用这种化合物治疗大麻素受体介导的疾病的方法。
• US7705024B2
  申请人：——

  公开号：US7705024B2

  公开（公告）日：2010-04-27