5-chloro-3-<3,5-dimethyl-4-<<3-(3-methyl-5-isoxazolyl)propyl>oxy>phenyl>-1,2,4-oxadiazole | 156787-18-7

• 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-chloro-3-<3,5-dimethyl-4-<<3-(3-methyl-5-isoxazolyl)propyl>oxy>phenyl>-1,2,4-oxadiazole
• 英文别名: 5-{3-[2,6-dimethyl-4-(5-chloro-1,2,4-oxadiazol-3yl)phenoxy]-propyl}-3-methylisoxazole；5-Chloro-3-[3,5-dimethyl-4-[3-(3-methyl-1,2-oxazol-5-yl)propoxy]phenyl]-1,2,4-oxadiazole
• CAS: 156787-18-7
• 化学式: C₁₇H₁₈ClN₃O₃
• 分子量: 347.801
• InChiKey: RBJFBFWNQYXQQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-甲基吡咯烷酮 、 5-chloro-3-<3,5-dimethyl-4-<<3-(3-methyl-5-isoxazolyl)propyl>oxy>phenyl>-1,2,4-oxadiazole 生成 5-{3-[2,6-Dimethyl-4-(5-sulfo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenoxy]-propyl}-3-methylisoxazole
  参考文献：
  名称：

  1,2,4-oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral

  摘要：

  公式为##STR1##的化合物，其中：R.sub.1为烷基，烷氧基，羟基，环烷基，羟基烷基，烷氧基烷基，羟基烷氧基，烷基硫代烷基，烷基亚砜基烷基，烷基磺酰基烷基，氨基烷基，烷基氨基烷基，二烷基氨基烷基，烷氧羰基，羧基或氰甲基；Y为碳原子数为3至9的烷基，R.sub.2和R.sub.3独立地为氢，烷基，烷氧基，卤素，氰基，三氟甲基和硝基；R.sub.4为烷氧基，羟基，卤甲基，二卤甲基，三卤甲基，二卤乙基，环烷基，杂环烷基，烷氧羰基，羟基烷基，烷氧基烷基，烷基羧酸酯氧基烷基，氰基，卤素，硫代烷基，烷基硫代烷基，烷基硫，硫，2,2,2-三氟乙基，(4-甲基苯基)磺酰氧甲基，N.dbd.Q或CON.dbd.Q，其中N.dbd.Q为氨基，烷基氨基或二烷基氨基；R.sub.5为氢或卤素或烷基。

  公开号：

  US05464848A1
• 作为产物：
  描述：

  N-hydroxy-3,5-dimethyl-4-<<3-(3-methyl-5-isoxazolyl)propyl>oxy>benzenecarboxamide imine 在 吡啶 、 potassium carbonate 、 三氯氧磷 作用下， 以 丙酮 为溶剂， 反应 8.0h， 生成 5-chloro-3-<3,5-dimethyl-4-<<3-(3-methyl-5-isoxazolyl)propyl>oxy>phenyl>-1,2,4-oxadiazole
  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

• 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