6-(3-(cyclopentyloxy)-4-methoxyphenyl)-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine | 1334336-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(3-(cyclopentyloxy)-4-methoxyphenyl)-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine
• 英文别名: 6-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine
• CAS: 1334336-05-8
• 化学式: C₂₂H₂₂N₄O₂S
• 分子量: 406.508
• InChiKey: ZKUCSKCBFSYHSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  86.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  异香兰素 在 manganese(IV) oxide 、 potassium carbonate 、 copper(ll) bromide 作用下， 以 乙醚 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 6-(3-(cyclopentyloxy)-4-methoxyphenyl)-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine
  参考文献：
  名称：

  Safety and Efficacy of New 3,6-diaryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine Analogs as Potential Phosphodiesterase-4 Inhibitors in NIH-3T3 Mouse Fibroblastic Cells

  摘要：

  A novel series of potential phosphodiesterase‐4 (PDE‐4) inhibitors, 6‐(3‐(cyclopentyloxy)‐4‐methoxyphenyl)‐3‐aryl‐7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazines, were developed. Different concentrations of the synthesized compounds were tested on cultured NIH‐3T3 cells to determine their safety and efficacy in NIH‐3T3 mouse fibroblastic cells in comparison with rolipram, a selective PDE‐4 inhibitor. The viability of cells was determined by (3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐di‐phenyltetrazoliumbromide (MTT) assay. The PDE inhibition rate was measured indirectly by determination of concentrations of extracellular cyclic adenosine monophosphate (cAMP) and cyclic guanosine monophosphate (cGMP) using enzyme‐linked immunoassay technique. The results showed that all tested compounds caused a marked increase in the concentration of cAMP, whereas the concentration of cGMP stayed approximately unchanged. The cytotoxic IC50 of all synthesized compounds was approximately twofold greater than their required concentration for inhibition of PDE‐4 (in terms of elevation of cAMP), and thus, these structures could be used to develop potent and safe inhibitors of PDE‐4 enzyme.

  DOI：

  10.1111/j.1747-0285.2011.01167.x