Chiral discrimination and antipicornavirus activity of 6-oxazolinylisoflavan.
Racemic 6-oxazolinylisoflavan, a highly effective inhibitor of rhinovirus serotype 1B in vitro, was resolved by high-performance liquid chromatography on a chiral stationary phase in order to study the activity of the enantiomers against picornaviruses. The absolute configuration of the two isomers was determined by circular dichroism curves. The antipicornavirus activity of each isomer, separately collected, was evaluated in vitro against human rhinovirus serotype 1B, enterovirus 71, echovirus 6, coxsackievirus B4, and poliovirus type 2 by means of the plaque reduction assay. Both enantiomers were inhibitors of picornavirus replication with the degree of their activity depending on virus and isomer tested.
Department of Pharmaceutical Studies, University of Rome La Sapienza, Italy.
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MG
Quaglia
N
N
Desideri
E
E
Bossù
I
I
Sestili
P
P
Tomao
C
C
Conti
N
N
Orsi
D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D006367:HeLa Cells; D006801:Humans; D007529:Isoflavones / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D008968:Molecular Conformation; D010080:Oxazoles / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D010849:Picornaviridae / Q000187:drug effects*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D010948:Viral Plaque Assay; D014779:Virus Replication / Q000187:drug effects
D000998:Antiviral Agents; D007529:Isoflavones; D010080:Oxazoles; C083553:6-oxazolinylisoflavan