(S)-5-{7-[4-(4,5-Dihydro-4-propyl-2-oxazolyl)phenoxy]heptyl}-3-methylisoxazole | 112270-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-5-{7-[4-(4,5-Dihydro-4-propyl-2-oxazolyl)phenoxy]heptyl}-3-methylisoxazole
• 英文别名: Isoxazole, 5-(7-(4-((4S)-4,5-dihydro-4-propyl-2-oxazolyl)phenoxy)heptyl)-3-methyl-；3-methyl-5-[7-[4-[(4S)-4-propyl-4,5-dihydro-1,3-oxazol-2-yl]phenoxy]heptyl]-1,2-oxazole
• CAS: 112270-41-4
• 化学式: C₂₃H₃₂N₂O₃
• 分子量: 384.519
• InChiKey: IHJKZKKDGUUCCM-FQEVSTJZSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  546.2±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 4-<<7-(3-methyl-5-isoxazolyl)heptyl>oxy>benzonitrile 在 盐酸 作用下， 反应 2.0h， 生成 (S)-5-{7-[4-(4,5-Dihydro-4-propyl-2-oxazolyl)phenoxy]heptyl}-3-methylisoxazole
  参考文献：
  名称：

  Enantiomeric effects of homologs of disoxaril on the inhibitory activity against human rhinovirus-14

  摘要：

  X-ray crystallography studies of racemic 5-[7-[4-(4,5-dihydro-4-methyl-2-oxazolyl)phenoxy]heptyl]- 3-methylisoxazole bound to human rhinovirus-14 (HRV-14) indicate selective binding of the S isomer. This result correlates well with the 10-fold greater activity of the S isomer as compared to the R isomer. The enantiomeric effect on activity is explained by a hydrophobic interaction of the methyl group in the case of 2a, with a pocket formed by Leu106 and Ser107. The 4-ethyl, 4-propyl, and 4-butyloxazolinyl homologues were prepared and tested against HRV-14. All of these compounds exhibited a comparable stereochemical effect. In each case, the S isomer displayed greater levels of activity than the R. The results of energetic considerations of the oxazoline ring in an 8-A pocket bound to the HRV-14 binding site suggest that the twist angle between the oxazoline and phenyl rings resulting from hydrophobic interactions of the alkyl substituents could be one of the determining factors for biological activity.

  DOI：

  10.1021/jm00398a009

文献信息

• DIANA, GUY D.;OTTO, MICHAEL J.;TREASURYWALA, ADI M.;MCKINLAY, MARK A.;OGL+, J. MED. CHEM., 31,(1988) N 3, 540-544
  作者：DIANA, GUY D.、OTTO, MICHAEL J.、TREASURYWALA, ADI M.、MCKINLAY, MARK A.、OGL+

  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
• US5002960A
  申请人：——

  公开号：US5002960A

  公开（公告）日：1991-03-26
• Enantiomeric effects of homologs of disoxaril on the inhibitory activity against human rhinovirus-14
  作者：Guy D. Diana、Michael J. Otto、Adi M. Treasurywala、Mark A. McKinlay、Richard C. Oglesby、Edward G. Maliski、Michael G. Rossmann、Thomas J. Smith

  DOI：10.1021/jm00398a009

  日期：1988.3

  X-ray crystallography studies of racemic 5-[7-[4-(4,5-dihydro-4-methyl-2-oxazolyl)phenoxy]heptyl]- 3-methylisoxazole bound to human rhinovirus-14 (HRV-14) indicate selective binding of the S isomer. This result correlates well with the 10-fold greater activity of the S isomer as compared to the R isomer. The enantiomeric effect on activity is explained by a hydrophobic interaction of the methyl group in the case of 2a, with a pocket formed by Leu106 and Ser107. The 4-ethyl, 4-propyl, and 4-butyloxazolinyl homologues were prepared and tested against HRV-14. All of these compounds exhibited a comparable stereochemical effect. In each case, the S isomer displayed greater levels of activity than the R. The results of energetic considerations of the oxazoline ring in an 8-A pocket bound to the HRV-14 binding site suggest that the twist angle between the oxazoline and phenyl rings resulting from hydrophobic interactions of the alkyl substituents could be one of the determining factors for biological activity.