5-[3-[2,6-Dimethyl-4-(2-methyltetrazol-5-yl)phenoxy]propyl]-3-isobutyl-isoxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-[3-[2,6-Dimethyl-4-(2-methyltetrazol-5-yl)phenoxy]propyl]-3-isobutyl-isoxazole
• 英文别名: 5-[3-[2,6-dimethyl-4-(2-methyltetrazol-5-yl)phenoxy]propyl]-3-(2-methylpropyl)-1,2-oxazole
• 化学式: C₂₀H₂₇N₅O₂
• 分子量: 369.467
• InChiKey: BOVCSKYAYYYJNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,5-二甲基-4-甲氧基苯甲腈 在 吡啶 、 N-氯代丁二酰亚胺 、 sodium azide 、 三溴化硼 、 potassium carbonate 、 氯化铵 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 58.0h， 生成 5-[3-[2,6-Dimethyl-4-(2-methyltetrazol-5-yl)phenoxy]propyl]-3-isobutyl-isoxazole
  参考文献：
  名称：

  Antipicornavirus activity of tetrazole analogs related to disoxaril

  摘要：

  A series of tetrazole analogues of Win 54954, a broad-spectrum antipicornavirus compound, has been synthesized to address the acid lability of the oxazoline ring of this series of compounds. The results of X-ray crystallography studies of several members of the oxazoline series bound to human rhinovirus type IA and 14 have been used to design compounds in the tetrazole series with a broad spectrum of activity. Compound 16b, which has a three-carbon linkage between the isoxazole and phenyl rings and a propyl chain extending from the isoxazole ring, exhibiting an MIC80 for 15 rhinovirus serotypes of 0.20 muM as compared to 0.40 muM for Win 54954. X-ray studies of 16b bound to human rhinovirus-14 show that the propyl side chain extends into a pore in the binding site with the possibility of hydrophobic interactions with a pocket formed by Leu106 and a portion of Ser107.

  DOI：

  10.1021/jm00074a004