Detail of "98034-32-3"

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

Enantiomeric effects of homologs of disoxaril on the inhibitory activity against human rhinovirus-14. Diana, Guy D.Except for chemicals metioned above, 98034-32-3 is also used.; Otto, Michael J.; Treasurywala, Adi M.; McKinlay, Mark A.; Oglesby, Richard C.; Maliski, Edward G.; Rossmann, Michael G.; Smith, Thomas J. (Sterling-Winthrop Res. Inst., Rensselaer, NY 12144, USA). J. Med. Chem., 31(3), 540-4 (English) 1988. CODEN: JMCMAR. ISSN: 0022-2623. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacology) X-ray crystallog. studies of racemic 5-[7-[4-(4,5-dihydro-4-methyl-2-oxazolyl)phenoxy]heptyl]-3-methylisoxaz ole (I) 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 Me group in the case of the S-isomer, with a pocket formed by Leu106 and Ser107. The 4-Et, 4-Pr, and 4-butyloxazolinyl homologs were tested against HRV-14. Synthesis of the Pr and Bu homologs in described. All of these compds. exhibited a comparable stereochem. effect. In each case, the S isomer displayed greater levels of activity than the R-isomer. The results of energetic considerations of the oxazoline ring in an 8-? pocket bound to the HRV-14 binding site suggest that the twist angle between the oxazoline and Ph rings resulting from hydrophobic interactions of the alkyl substituents could be one of the detg. factors for biol. activity. .