2-(4-benzyloxyphenyl)-4,5-dihydrooxazole | 151250-16-7

• 英文名称: 2-(4-benzyloxyphenyl)-4,5-dihydrooxazole
• 英文别名: 2-(4-Phenylmethoxyphenyl)-4,5-dihydro-1,3-oxazole
• CAS: 151250-16-7
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: VSEIWCZUCMSMHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-benzyloxyphenyl)-4,5-dihydrooxazole 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以75%的产率得到4-(4,5-二氢-2-噁唑)苯酚
  参考文献：
  名称：

  The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors

  摘要：

  A series of para-substituted phenolic N-alkyl carbamates were evaluated for their FAAH and MGL inhibitory activities. The compounds were generally selective for FAAH, with IC50 values in the nM range, whereas inhibition of MGL required concentrations three orders of magnitude higher. The most potent compounds, dodecylcarbamic acid 4-(4,5-dihydrothiazol-2-yl)phenyl (12) and 4-(1,2,3-thiadiazol-4-yl)phenyl (26) esters, inhibited FAAH and MGL with IC50 values at the low-nanomolar (IC(50)s: 0.0063 and 0.012 mu M) and the low-micromolar ranges (IC(50)s; 2.1 and 1.0 mu M), respectively. Compound 26 also inhibited both FAAH-dependent AEA uptake and AEA hydrolysis (IC50; 0.082 mu M) by intact RBL2H3 cells, and could also reduce 2-AG hydrolysis by these cells at concentrations >= 0.030 mu M. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.007
• 作为产物：
  描述：

  4-苯甲氧基苯甲腈 、 C.I.酸性橙108 在 zinc(II) chloride 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以50%的产率得到2-(4-benzyloxyphenyl)-4,5-dihydrooxazole
  参考文献：
  名称：

  The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors

  摘要：

  A series of para-substituted phenolic N-alkyl carbamates were evaluated for their FAAH and MGL inhibitory activities. The compounds were generally selective for FAAH, with IC50 values in the nM range, whereas inhibition of MGL required concentrations three orders of magnitude higher. The most potent compounds, dodecylcarbamic acid 4-(4,5-dihydrothiazol-2-yl)phenyl (12) and 4-(1,2,3-thiadiazol-4-yl)phenyl (26) esters, inhibited FAAH and MGL with IC50 values at the low-nanomolar (IC(50)s: 0.0063 and 0.012 mu M) and the low-micromolar ranges (IC(50)s; 2.1 and 1.0 mu M), respectively. Compound 26 also inhibited both FAAH-dependent AEA uptake and AEA hydrolysis (IC50; 0.082 mu M) by intact RBL2H3 cells, and could also reduce 2-AG hydrolysis by these cells at concentrations >= 0.030 mu M. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.007