3-(4-chlorophenyl)-5-n-propylthio-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-chlorophenyl)-5-n-propylthio-1,2,4-triazole
• 英文别名: 5-(4-chlorophenyl)-3-propylsulfanyl-1H-1,2,4-triazole
• 化学式: C₁₁H₁₂ClN₃S
• mdl: MFCD27927018
• 分子量: 253.755
• InChiKey: QYSMFMYLOLQHEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 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：

  二甲氨基甲酰氯 、 3-(4-chlorophenyl)-5-n-propylthio-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75%的产率得到3-(4-chlorophenyl)-N,N-dimethyl-5-(propylthio)-1H-1,2,4-triazole-1-carboxamide
  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
• 作为产物：
  描述：

  4-氯苯甲酰氯 在 三乙胺 作用下， 以 甲醇 、 苯 为溶剂， 反应 43.0h， 生成 3-(4-chlorophenyl)-5-n-propylthio-1,2,4-triazole
  参考文献：
  名称：

  Synthesis and Evaluation of Anti-inflammatory and Analgesic Activities of New 1,2,4-triazole Derivatives

  摘要：

  在本研究中，报道了八种新型5-硫代烷基-1,3-二芳基-1,2,4-三唑衍生物的合成、抗炎及镇痛活性。对于抗炎研究，采用了卡拉胶诱导的大鼠足跖肿胀模型。测试化合物分别以50 mg/kg和100 mg/kg的剂量通过腹腔注射后测定足跖肿胀情况。结果表明，与参考药物吲哚美辛相比，某些化合物显示出良好的活性。在镇痛活性方面，测试化合物在50 mg/kg和100 mg/kg剂量下通过腹腔注射，运用尾部甩击测试模型进行研究。它们的镇痛活性通过30分钟后的潜伏期时间测定来确定。统计分析显示，与50 mg/kg剂量的对照组相比，所有测试化合物均呈现出24%至47%的痛觉减退活性。然而，所有经测试的化合物镇痛活性均低于标准药物吗啡。

  DOI：

  10.2174/1573406410666140613154507