methyl 5-<3-<2,6-dimethyl-4-<5-(2-methyl-2H-tetrazolyl)>phenoxy>propyl>-3-isoxazoleacetate | 152775-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 5-<3-<2,6-dimethyl-4-<5-(2-methyl-2H-tetrazolyl)>phenoxy>propyl>-3-isoxazoleacetate
• 英文别名: methyl 2-[5-[3-[2,6-dimethyl-4-(2-methyltetrazol-5-yl)phenoxy]propyl]-1,2-oxazol-3-yl]acetate
• CAS: 152775-58-1
• 化学式: C₁₉H₂₃N₅O₄
• 分子量: 385.423
• InChiKey: FNBZJIPKUNEDDD-UHFFFAOYSA-N

物化性质

• 沸点：
  590.6±60.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  105.16
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 5-<3-<2,6-dimethyl-4-<5-(2-methyl-2H-tetrazolyl)>phenoxy>propyl>-3-isoxazoleacetate 在 lithium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以94.9%的产率得到5-<3-<2,6-dimethyl-4-<5-(2-methyl-2H-tetrazolyl)>phenoxy>propyl>-3-isoxazoleacetic acid
  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
• 作为产物：
  描述：

  3,5-二甲基-4-甲氧基苯甲腈 在 bis-triphenylphosphine-palladium(II) chloride 、 lithium aluminium tetrahydride 、 sodium azide 、 溴 、 sodium acetate 、 三溴化硼 、 tribenzylamine hydrochloride 、 potassium carbonate 、 氯化铵 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 72.67h， 生成 methyl 5-<3-<2,6-dimethyl-4-<5-(2-methyl-2H-tetrazolyl)>phenoxy>propyl>-3-isoxazoleacetate
  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