3-Methyl-5-[3-(3,5,4'-trimethyl-biphenyl-4-yloxy)-propyl]-isoxazole

• 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: 3-Methyl-5-[3-(3,5,4'-trimethyl-biphenyl-4-yloxy)-propyl]-isoxazole
• 英文别名: 5-[3-[2,6-Dimethyl-4-(p-tolyl)phenoxy]propyl]-3-methyl-isoxazole；5-[3-[2,6-dimethyl-4-(4-methylphenyl)phenoxy]propyl]-3-methyl-1,2-oxazole
• 化学式: C₂₂H₂₅NO₂
• 分子量: 335.446
• InChiKey: CZZQIHRLIRTTSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-碘甲苯 、 3-<3-<2,6-dimethyl-4-(tributylstannyl)phenoxy>propyl>-3-methylisoxazole 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以50%的产率得到3-Methyl-5-[3-(3,5,4'-trimethyl-biphenyl-4-yloxy)-propyl]-isoxazole
  参考文献：
  名称：

  [(Biaryloxy)alkyl]isoxazoles: Picornavirus Inhibitors

  摘要：

  A series of biphenyl analogs, 6, of 5-[5-(2,6-dichloro-5-oxazolylphenoxy)pentyl]-3-methylisoxazole (2) have been synthesized and tested in vitro against 10 human rhinovirus serotypes in a TCID50 assay. The most potent compound in the series 6s, 3-[3-[2,6-dimethyl-4-(4-fluorophenyl)phenoxy]propyl]-3-methylisoxazole, was screened against an additional 84 serotypes. It was found to be active against 64 of the serotypes, while 87 serotypes were sensitive to 2 at <3 mu g/mL. On comparison of the active serotypes, 6s exhibited greater potency versus 2. Analogs 6a-c,s were examined for in vitro metabolic stability by monkey liver microsomal assay. These analogs exhibited a greater than 7-fold improvement (t(1/2) > 200 min) in metabolic stability compared with 2 (t(1/2) > 27 min).

  DOI：

  10.1021/jm00014a029

文献信息

• [(Biaryloxy)alkyl]isoxazoles: Picornavirus Inhibitors
  作者：Joseph W. Guiles、Guy D. Diana、Daniel C. Pevear

  DOI：10.1021/jm00014a029

  日期：1995.7

  A series of biphenyl analogs, 6, of 5-[5-(2,6-dichloro-5-oxazolylphenoxy)pentyl]-3-methylisoxazole (2) have been synthesized and tested in vitro against 10 human rhinovirus serotypes in a TCID50 assay. The most potent compound in the series 6s, 3-[3-[2,6-dimethyl-4-(4-fluorophenyl)phenoxy]propyl]-3-methylisoxazole, was screened against an additional 84 serotypes. It was found to be active against 64 of the serotypes, while 87 serotypes were sensitive to 2 at <3 mu g/mL. On comparison of the active serotypes, 6s exhibited greater potency versus 2. Analogs 6a-c,s were examined for in vitro metabolic stability by monkey liver microsomal assay. These analogs exhibited a greater than 7-fold improvement (t(1/2) > 200 min) in metabolic stability compared with 2 (t(1/2) > 27 min).