4-Oxazolemethanol, 4,5-dihydro-2-(4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)phenyl)- | 98033-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Oxazolemethanol, 4,5-dihydro-2-(4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)phenyl)-
• 英文别名: [2-[4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]phenyl]-4,5-dihydro-1,3-oxazol-4-yl]methanol
• CAS: 98033-99-9
• 化学式: C₂₁H₂₈N₂O₄
• 分子量: 372.464
• InChiKey: UZLKTKMUKCZQRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,5-二甲基异唑 在 盐酸 、 正丁基锂 、 TEA 作用下， 以 乙醚 为溶剂， 反应 7.0h， 生成 4-Oxazolemethanol, 4,5-dihydro-2-(4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)phenyl)-
  参考文献：
  名称：

  [[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating

  摘要：

  A series of [[(4,5-dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles has been synthesized and evaluated as antipicornavirus agents. The effect of alkyl groups in the 4- and 5-position of the oxazoline ring, as well as the alkyl chain length, on antiviral activity was examined. Compound 14 was evaluated in vivo and was found to significantly reduce mortality at an oral dose of 4 mg/kg in mice infected intracerebrally with poliovirus-2. Compound 14 was also effective in preventing paralysis when administered intraperitoneally to mice infected subcutaneously with a lethal dose of ECHO-9 virus. On the basis of the results of these studies, compound 14 is a strong candidate for clinical evaluation as a systemic agent for the treatment of picornavirus infections.

  DOI：

  10.1021/jm00150a025

文献信息

• (Substituted) Phenyl-aliphatic-isoxazoles useful as antiviral agents and preparation thereof
  申请人：STERLING WINTHROP INC.

  公开号：EP0137242A2

  公开（公告）日：1985-04-17

  Compounds of the formulas and wherein R is lower-alkyl or substituted-lower-alkyl; R1, R2, R3 and R4 are each hydrogen, lower-alkyl or substituted lower-alkyl; R5 is hydrogen, lower-alkyl, halogen, nitro, lower-alkoxy, lower-alkylthio or trifluoromethyl; R6 is lower-alkyl; X is 0 or a single bond; and n is an integer from 3 to 9, are useful as antiviral agents, especially against picomaviruses.

  公式如下的化合物 和 其中 R 是低级烷基或取代的低级烷基；R1、R2、R3 和 R4 分别是氢、低级烷基或取代的低级烷基；R5 是氢、低级烷基、卤素、硝基、低级烷氧基、低级烷硫基或三氟甲基；R6 是低级烷基；X 是 0 或单键；n 是 3 至 9 的整数。
• 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.
• DIANA, G. D.;MCKINLAY, M. A.;OTTO, M. J.;AKULLIAN, V.;OGLESBY, C., J. MED. CHEM., 1985, 28, N 12, 1906-1910
  作者：DIANA, G. D.、MCKINLAY, M. A.、OTTO, M. J.、AKULLIAN, V.、OGLESBY, C.

  DOI：——

  日期：——
• US4843087A
  申请人：——

  公开号：US4843087A

  公开（公告）日：1989-06-27
• US4939267A
  申请人：——

  公开号：US4939267A

  公开（公告）日：1990-07-03