5-{5-[4-(2-furanyl)-2,6-dimethylphenoxy]pentyl}-3-methylisoxazole | 107311-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-{5-[4-(2-furanyl)-2,6-dimethylphenoxy]pentyl}-3-methylisoxazole
• 英文别名: 5-[5-[4-(2-Furyl)-2,6-dimethyl-phenoxy]pentyl]-3-methyl-isoxazole；5-[5-[4-(furan-2-yl)-2,6-dimethylphenoxy]pentyl]-3-methyl-1,2-oxazole
• CAS: 107311-59-1
• 化学式: C₂₁H₂₅NO₃
• 分子量: 339.434
• InChiKey: WEYYFURNQSORFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(5-溴戊基)-3-甲基异恶唑 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 5-{5-[4-(2-furanyl)-2,6-dimethylphenoxy]pentyl}-3-methylisoxazole
  参考文献：
  名称：

  A model for compounds active against human rhinovirus-14 based on x-ray crystallography data

  摘要：

  A number of (oxazolinylphenyl)isoxazoles have been synthesized and tested against human rhinovirus-14 (HRV-14). Several of the more active compounds have been examined by X-ray crystallography and their orientation in the compound binding site on the capsid protein of HRV-14 has been determined. Based on the minimum inhibitory concentration against HRV-14 and the X-ray conformation of the compounds, a model has been developed which distinguishes between the space-filling properties of the active and inactive compounds in this series. The model was generated by overlaying composite structures and comparing the van der Waals generated volume maps. The results of this study indicate that inactive compounds display areas of excessive bulk particularly around the phenyl ring, while the active compounds occupy space below the pore area of the compound binding site.

  DOI：

  10.1021/jm00167a006

文献信息

• Heterocyclic substituted-phenoxyalkylisoxazoles as antiviral useful
  申请人：Sterling Drug Inc.

  公开号：US04857539A1

  公开（公告）日：1989-08-15

  Compounds of the formula ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms; Z is N or HC; R is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when Z is N, R is lower-alkyl; R.sub.1 and R.sub.2 are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; and Het is selected from specified heterocyclic groups, are useful and antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.

  化合物的公式为##STR1##其中：Y是3-9个碳原子的烷基桥；Z是N或HC；R是氢或1-5个碳原子的低烷基，但当Z是N时，R是低烷基；R.sub.1和R.sub.2是氢、卤素、低烷基、低烷氧基、硝基、低烷氧羰基或三氟甲基；Het从指定的杂环基团中选择，对抗病毒剂，特别是对抗小RNA病毒，包括多种鼻病毒菌株。
• Heterocyclic substituted-phenoxyalkyl-isoxazoles and-furans, their preparation and use as antiviral agents
  申请人：STERLING WINTHROP INC.

  公开号：EP0207453A2

  公开（公告）日：1987-01-07

  Compounds of the formula are disclosed, wherein: Y is an alkylene bridge of 3-9 carbon atoms; Z is N or HC; R is hydrogen or lower-alkyl of 1-3 carbon atoms, with the proviso that when Z is N, R is lower-alkyl; R1 and R2 are each hydrogen, halogen, methyl, nitro, lower-alkoxycarbonyl or trifluoromethyl; and Het is a heterocyclic group, and pharmaceutically acceptable acid addition salts thereof, as well as methods for preparation and use thereof. The compounds exhibit valuable antiviral properties.

  公开了式 公开了式 Y 是 3-9 个碳原子的亚烷基桥； Z 是 N 或 HC R 是氢或 1-3 个碳原子的低级烷基，但当 Z 是 N 时，R 是低级烷基； R1 和 R2 分别是氢、卤素、甲基、硝基、低级烷氧基羰基或三氟甲基；以及 Het 是杂环基团，及其药学上可接受的酸加成盐，以及其制备和使用方法。这些化合物具有宝贵的抗病毒特性。
• US4857539A
  申请人：——

  公开号：US4857539A

  公开（公告）日：1989-08-15
• A model for compounds active against human rhinovirus-14 based on x-ray crystallography data
  作者：Guy D. Diana、Adi M. Treasurywala、Thomas R. Bailey、Richard C. Oglesby、Daniel C. Pevear、Frank J. Dutko

  DOI：10.1021/jm00167a006

  日期：1990.5

  A number of (oxazolinylphenyl)isoxazoles have been synthesized and tested against human rhinovirus-14 (HRV-14). Several of the more active compounds have been examined by X-ray crystallography and their orientation in the compound binding site on the capsid protein of HRV-14 has been determined. Based on the minimum inhibitory concentration against HRV-14 and the X-ray conformation of the compounds, a model has been developed which distinguishes between the space-filling properties of the active and inactive compounds in this series. The model was generated by overlaying composite structures and comparing the van der Waals generated volume maps. The results of this study indicate that inactive compounds display areas of excessive bulk particularly around the phenyl ring, while the active compounds occupy space below the pore area of the compound binding site.