3-(4-chloro-phenyl)-5-cyclopropylmethylsulfanyl-1H-[1,2,4]triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-chloro-phenyl)-5-cyclopropylmethylsulfanyl-1H-[1,2,4]triazole
• 英文别名: 3-(4-chlorophenyl)-5-((cyclopropylmethyl)thio)-1H-1,2,4-triazole；3-(4-chlorophenyl)-5-(cyclopropylmethylsulfanyl)-1H-1,2,4-triazole；5-(4-chlorophenyl)-3-(cyclopropylmethylsulfanyl)-1H-1,2,4-triazole
• 化学式: C₁₂H₁₂ClN₃S
• 分子量: 265.766
• InChiKey: ACCZGLPWKYSXJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-哌啶酰氯 、 3-(4-chloro-phenyl)-5-cyclopropylmethylsulfanyl-1H-[1,2,4]triazole 在 三乙烯二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以56%的产率得到(3-(4-chlorophenyl)-5-(cyclopropylmethylthio)-1H-1,2,4-triazol-1-yl)(piperidin-1-yl)methanone
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship for a Novel Class of Potent and Selective Carbamoyl-Triazole Based Inhibitors of Hormone Sensitive Lipase

  摘要：

  The central role of the intracellular enzyme hormone-sensitive lipase (HSL) in regulating fatty acid metabolism makes it an interesting pharmacological target for the treatment of insulin resistant and dyslipidemic disorders where a decrease in delivery of fatty acids to the circulation is desirable, e.g., in individuals with type 2 diabetes, metabolic syndrome, or impaired glucose tolerance. On the basis of a lead structure from high throughput screening, we have identified a very potent type of carbamoyl-triazole inhibitors of HSL. As part of the lead optimization program, four new classes of carbamoyl-triazoles were synthesized and tested with respect to potency, efficacy and selectivity. Methyl-phenyl-carbamoyl-triazoles were identified as potent and efficacious HSL inhibitors. These compounds do not inhibit other hydrolases such as hepatic lipase, lipoprotein lipase, pancreatic lipase, and butyrylcholine esterase. However, the inhibitors 4b and 4g with IC50 values for HSL of 0.17 and 0.25 muM, respectively, were the only inhibitors selective against acetylcholine esterase. A reversible pseudosubstrate inhibition mechanism is proposed for this class of inhibitors.

  DOI：

  10.1021/jm031004s