acetic acid, <3-<3,5-dimethyl-4-<<3-(3-methyl-5-isoxazolyl)propyl>oxy>phenyl>-1,2,4-oxadiazol-5-yl>methyl ester | 153168-13-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: acetic acid, <3-<3,5-dimethyl-4-<<3-(3-methyl-5-isoxazolyl)propyl>oxy>phenyl>-1,2,4-oxadiazol-5-yl>methyl ester
• 英文别名: [3-[3,5-Dimethyl-4-[3-(3-methyl-1,2-oxazol-5-yl)propoxy]phenyl]-1,2,4-oxadiazol-5-yl]methyl acetate
• CAS: 153168-13-9
• 化学式: C₂₀H₂₃N₃O₅
• 分子量: 385.42
• InChiKey: XLDDEMWAFFDBKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  acetic acid, <3-<3,5-dimethyl-4-<<3-(3-methyl-5-isoxazolyl)propyl>oxy>phenyl>-1,2,4-oxadiazol-5-yl>methyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以91.2%的产率得到[3-[3,5-Dimethyl-4-[3-(3-methylisoxazol-5-yl)propoxy]phenyl]-1,2,4-oxadiazol-5-yl]methanol
  参考文献：
  名称：

  Oxadiazoles as Ester Bioisosteric Replacements in Compounds Related to Disoxaril. Antirhinovirus Activity

  摘要：

  A series of 1,2,4-oxadiazoles has been prepared as ester bioisosteres and tested against 15 human rhinovirus serotypes, and the MIC(80), the concentration which inhibits 80% or 12 of the serotypes tested, was determined. Homologation of the alkyl group attached to the oxadiazole ring resulted in a reduction in activity with increased chain length. Introduction of hydrophilic groups in this position rendered the compounds inactive. Increasing the length of the side chain attached to the isoxazole ring resulted in an increase in activity. Replacement of the methyl with alkoxyalkyl substituents retained activity; however, introduction of a hydroxyl group on to the side chain reduced activity. Compound 8a, where both the isoxazole and oxadiazole rings were substituted with methyl groups, was one of the most active compounds in the series. A comparison was made between 8a and the two isomeric oxadiazoles 41 and 46, and an attempt was made to explain the difference in activity by examining electrostatic potential maps and by an energy profiling study. No conclusive results were obtained from these studies.

  DOI：

  10.1021/jm00041a022
• 作为产物：
  描述：

  5-(3-氯丙基)-3-甲基异噁唑 在 盐酸羟胺 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 79.0h， 生成 acetic acid, <3-<3,5-dimethyl-4-<<3-(3-methyl-5-isoxazolyl)propyl>oxy>phenyl>-1,2,4-oxadiazol-5-yl>methyl ester
  参考文献：
  名称：

  Oxadiazoles as Ester Bioisosteric Replacements in Compounds Related to Disoxaril. Antirhinovirus Activity

  摘要：

  A series of 1,2,4-oxadiazoles has been prepared as ester bioisosteres and tested against 15 human rhinovirus serotypes, and the MIC(80), the concentration which inhibits 80% or 12 of the serotypes tested, was determined. Homologation of the alkyl group attached to the oxadiazole ring resulted in a reduction in activity with increased chain length. Introduction of hydrophilic groups in this position rendered the compounds inactive. Increasing the length of the side chain attached to the isoxazole ring resulted in an increase in activity. Replacement of the methyl with alkoxyalkyl substituents retained activity; however, introduction of a hydroxyl group on to the side chain reduced activity. Compound 8a, where both the isoxazole and oxadiazole rings were substituted with methyl groups, was one of the most active compounds in the series. A comparison was made between 8a and the two isomeric oxadiazoles 41 and 46, and an attempt was made to explain the difference in activity by examining electrostatic potential maps and by an energy profiling study. No conclusive results were obtained from these studies.

  DOI：

  10.1021/jm00041a022

文献信息

• 1,2,4-Oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral agents
  申请人：SANOFI

  公开号：EP0566199B1

  公开（公告）日：2000-03-01
• US5349068A
  申请人：——

  公开号：US5349068A

  公开（公告）日：1994-09-20
• US5464848A
  申请人：——

  公开号：US5464848A

  公开（公告）日：1995-11-07
• US5643929A
  申请人：——

  公开号：US5643929A

  公开（公告）日：1997-07-01