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

…, MJ Otto, AM Treasurywala, MA McKinlay…

Index: Diana; Otto; Treasurywala; McKinlay; Oglesby; Maliski; Rossmann; Smith Journal of Medicinal Chemistry, 1988 , vol. 31, # 3 p. 540 - 544

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Citation Number: 26

Abstract

X-ray crystallography studies of racemic 5-[7-[4-(4, 5-dihydro-4-methyl-2-oxazolyl) phenoxy] heptyl]-3-methylisoxazole (2) 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 ...