3-Ethylsulfanyl-5-(4-methoxy-phenyl)-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-Ethylsulfanyl-5-(4-methoxy-phenyl)-1H-[1,2,4]triazole
• 英文别名: 3-ethylsulfanyl-5-(4-methoxyphenyl)-1H-1,2,4-triazole
• 化学式: C₁₁H₁₃N₃OS
• mdl: MFCD27935356
• 分子量: 235.31
• InChiKey: PAOYRSQBPUNNTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Ethylsulfanyl-5-(4-methoxy-phenyl)-1H-[1,2,4]triazole 、 对氟苯甲砜 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 20.33h， 以33%的产率得到5-Ethylsulfanyl-1-(4-methanesulfonyl-phenyl)-3-(4-methoxy-phenyl)-1H-[1,2,4]triazole
  参考文献：
  名称：

  5-烷硫基-1,3-二芳基-1,2,4-三唑的合成

  摘要：

  容易获得的3-烷硫基-5-芳基-1,2,4-三唑的丙烯酸化以中等收率得到5-烷硫基-1,3-二芳基-1,2,4-三唑。后者的结构通过NOE和13 C-NMR确认。

  DOI：

  10.1002/jhet.5570410209
• 作为产物：
  描述：

  溴乙烷 、 alkaline earth salt of/the/ methylsulfuric acid 生成 3-Ethylsulfanyl-5-(4-methoxy-phenyl)-1H-[1,2,4]triazole
  参考文献：
  名称：

  Mndshojan et al., Izvestiya Akademii Nauk Armyanskoi SSR, Khimicheskie Nauki, 1957, vol. 10, p. 357,359,360

  摘要：

  DOI：

文献信息

• Synthesis and Structure−Activity Relationship for a Novel Class of Potent and Selective Carbamoyl-Triazole Based Inhibitors of Hormone Sensitive Lipase
  作者：Søren Ebdrup、Lotte Gottlieb Sørensen、Ole Hvilsted Olsen、Poul Jacobsen

  DOI：10.1021/jm031004s

  日期：2004.1.1

  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.