tert-butyl 4-(4-((2-fluoro-4-(1H-tetrazol-1-yl)phenoxy)methyl)thiazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl 4-(4-((2-fluoro-4-(1H-tetrazol-1-yl)phenoxy)methyl)thiazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate
• 英文别名: tert-butyl 4-[4-[[2-fluoro-4-(tetrazol-1-yl)phenoxy]methyl]-1,3-thiazol-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylate
• 化学式: C₂₁H₂₃FN₆O₃S
• 分子量: 458.516
• InChiKey: AKCKRXDXJOJOTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  95.26
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(4-((2-fluoro-4-(1H-tetrazol-1-yl)phenoxy)methyl)thiazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到4-((2-fluoro-4-(1H-tetrazol-1-yl)phenoxy)methyl)-2-(1,2,3,6-tetrahydropyridin-4-yl)thiazole
  参考文献：
  名称：

  Design and biological evaluation of tetrahydropyridine derivatives as novel human GPR119 agonists

  摘要：

  A series of novel tetrahydropyridine derivatives were prepared and evaluated using cell-based measurements. Systematic optimization of general structure G-1 led to the identification of compound 35 (EC50 = 4.9 nM) and 37 (EC50 = 8.8 nM) with high GPR119 agonism activity and moderate clog P. Through single and long-term pharmacodynamic experiments, we found that compound 35 showed a hypoglycemic effect and may have an effect on improving basal metabolic rate in DIO mice. Both in vitro and in vivo tests indicated that compound 35 was a potential potent GPR119 agonist in allusion to T2DM treatment.

  DOI：

  10.1016/j.bmcl.2019.126855
• 作为产物：
  描述：

  4-氨基-2-氟苯酚 在 sodium azide 、 caesium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 tert-butyl 4-(4-((2-fluoro-4-(1H-tetrazol-1-yl)phenoxy)methyl)thiazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate
  参考文献：
  名称：

  Design and biological evaluation of tetrahydropyridine derivatives as novel human GPR119 agonists

  摘要：

  A series of novel tetrahydropyridine derivatives were prepared and evaluated using cell-based measurements. Systematic optimization of general structure G-1 led to the identification of compound 35 (EC50 = 4.9 nM) and 37 (EC50 = 8.8 nM) with high GPR119 agonism activity and moderate clog P. Through single and long-term pharmacodynamic experiments, we found that compound 35 showed a hypoglycemic effect and may have an effect on improving basal metabolic rate in DIO mice. Both in vitro and in vivo tests indicated that compound 35 was a potential potent GPR119 agonist in allusion to T2DM treatment.

  DOI：

  10.1016/j.bmcl.2019.126855