N,N-Dimethyl-3-biphenyl-4-yl-5-methylsulfanyl-[1,2,4]triazole-1-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-Dimethyl-3-biphenyl-4-yl-5-methylsulfanyl-[1,2,4]triazole-1-carboxamide
• 英文别名: 3-Biphenyl-4-yl-5-methylsulfanyl-[1,2,4]triazole-1-carboxylic acid dimethylamide；N,N-dimethyl-5-methylsulfanyl-3-(4-phenylphenyl)-1,2,4-triazole-1-carboxamide
• 化学式: C₁₈H₁₈N₄OS
• 分子量: 338.433
• InChiKey: YKUXAAJJGAYTRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二甲氨基甲酰氯 、 3-methylsulfanyl-5-(4-phenylphenyl)-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80%的产率得到N,N-Dimethyl-3-biphenyl-4-yl-5-methylsulfanyl-[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

文献信息

• Compounds and uses thereof for decreasing activity of hormone-sensitive lipase
  申请人：——

  公开号：US20030166644A1

  公开（公告）日：2003-09-04

  Use of compounds to inhibit hormone-sensitive lipase, pharmaceutical compositions comprising the compounds, methods of treatment employing these compounds and compositions, and novel compounds. The present compounds are inhibitors of hormone-sensitive lipase and may be useful in the treatment and/or prevention of medical disorders where a decreased activity of hormone-sensitive lipase is desirable.

  使用化合物抑制激素敏感性脂肪酶，包括这些化合物的药物组合物，使用这些化合物和组合物的治疗方法，以及新化合物。目前的化合物是激素敏感性脂肪酶的抑制剂，可能在治疗和/或预防需要降低激素敏感性脂肪酶活性的医学疾病中有用。
• Use of compounds for decreasing activity of hormone-sensitive
  申请人：——

  公开号：US20030166690A1

  公开（公告）日：2003-09-04

  Use of compounds to inhibit hormone-sensitive lipase, pharmaceutical compositions comprising the compounds, methods of treatment employing these compounds and compositions, and novel compounds. The present compounds are inhibitors of hormone-sensitive lipase and may be useful in the treatment and/or prevention of medical disorders where a decreased activity of hormone-sensitive lipase is desirable.

  使用化合物来抑制激素敏感性脂肪酶，包括这些化合物的制药组合物，使用这些化合物和组合物的治疗方法，以及新颖的化合物。这些化合物是激素敏感性脂肪酶的抑制剂，可用于治疗和/或预防需要降低激素敏感性脂肪酶活性的医学疾病。
• COMPOSITIONS FOR DECREASING ACTIVITY OF HORMONE-SENSITIVE LIPASE
  申请人：NOVO NORDISK A/S

  公开号：EP1458375A2

  公开（公告）日：2004-09-22
• COMPOUNDS AND USES THEREOF FOR DECREASING ACTIVITY OF HORMONE-SENSITIVE LIPASE
  申请人：NOVO NORDISK A/S

  公开号：EP1458374A2

  公开（公告）日：2004-09-22
• US7067517B2
  申请人：——

  公开号：US7067517B2

  公开（公告）日：2006-06-27