1-<5-<3-<2,6-dimethyl-4-<5-(2-methyl-2H-tetrazolyl)>phenoxy>propyl>-3-isoxazolyl>-2-propanone | 152775-61-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-<5-<3-<2,6-dimethyl-4-<5-(2-methyl-2H-tetrazolyl)>phenoxy>propyl>-3-isoxazolyl>-2-propanone
• 英文别名: 1-[5-[3-[2,6-dimethyl-4-(2-methyltetrazol-5-yl)phenoxy]propyl]-1,2-oxazol-3-yl]propan-2-one
• CAS: 152775-61-6
• 化学式: C₁₉H₂₃N₅O₃
• 分子量: 369.423
• InChiKey: CPYWFRCNSVKUBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  27.0
• 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：
  95.93
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-<5-<3-<2,6-dimethyl-4-<5-(2-methyl-2H-tetrazolyl)>phenoxy>propyl>-3-isoxazolyl>-2-propanone 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以75%的产率得到α-methyl-5-<3-<2,6-dimethyl-4-<5-(2-methyl-2H-tetrazolyl)>phenoxy>propyl>-3-isoxazolyleethanol
  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：

  ethyl 5-<3-<2,6-dimethyl-4-<5-(2-methyl-2H-tetrazolyl)>phenoxy>propyl>-3-isoxazolecarboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 lithium hydroxide 、 lithium aluminium tetrahydride 、 水 、 溴 、 sodium acetate 、 tribenzylamine hydrochloride 、 三苯基膦 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 39.67h， 生成 1-<5-<3-<2,6-dimethyl-4-<5-(2-methyl-2H-tetrazolyl)>phenoxy>propyl>-3-isoxazolyl>-2-propanone
  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