5-(5-(cyclopropylethynyl)thiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester | 1020106-56-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(5-(cyclopropylethynyl)thiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-[5-(2-cyclopropylethynyl)thiophen-2-yl]-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylate
• CAS: 1020106-56-2
• 化学式: C₂₂H₁₈Cl₂N₂O₂S
• 分子量: 445.369
• InChiKey: VNAKGQPPWMTVFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  5-(5-(cyclopropylethynyl)thiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester 在 甲醇 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 以93%的产率得到5-(5-(cyclopropylethynyl)thiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid
  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
• 作为产物：
  描述：

  5-(5-bromothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester 、 环丙乙炔 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91%的产率得到5-(5-(cyclopropylethynyl)thiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  THIOPHENE COMPOUNDS

  摘要：

  本发明涉及如下所示的公式（I）的噻吩化合物：公式（I）中的每个变量在规范中有定义。这些化合物可用于治疗大麻素受体介导的疾病。

  公开号：

  US20080090810A1

文献信息

• Thiophene Compounds
  申请人：Shia Kak-shan

  公开号：US20090029969A2

  公开（公告）日：2009-01-29

  This invention relates to thiophene compounds of formula (I) shown below: Each variable in formula (I) is defined in the specification. These compounds can be used to treat cannabinoid-receptor mediated disorders.
• US7834046B2
  申请人：——

  公开号：US7834046B2

  公开（公告）日：2010-11-16