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Fluoro-substituted flavones and 2-styrykhromones, related to natural and synthetic flavonoids previously described, were prepared, characterized and tested for anti-rhinovirus activity. Structural elucidation of the new compounds was performed by IR, NMR spectra and X-ray crystal structure analysis for 6-fluoro-3-hydroxy-2-styrylchromone. The antiviral potency was evaluated by a plaque reduction assay in HeLa cell cultures infected with rhinoviruses 1B and 14, selected as representative serotypes for viral groups B and A of human rhinoviruses, respectively. In comparison with results previously obtained, the introduction of the fluorine atom seems to exert a positive influence on the activity against serotype 14 while counteracting the effect against serotype 1B.

Recently, we identified 2-styrylchromones as a new class of antirhinovirus flavonoids with moderate activity against both rhinovirus groups A and B. In order to improve the antiviral effect of the first series of tested 2-styrylchromones, a hydroxy or methoxy group was introduced in position 3 of the chromone ring. Cytotoxicity and antiviral activity of the new synthesized compounds were evaluated in HeLa cell cultures infected with rhinoviruses 1B and 14, selected as representative serotypes for viral groups B and A of human rhinoviruses (HRVs), respectively. These antiviral results compared to those obtained for 3-unsubstituted 2-styrylchromones indicate the greater potency of 3-hydroxy and 3-methoxy derivatives against both serotypes.

Fenticonazole, a topical antifungal agent containing a stereogenic centre, is used in therapy as a racemic mixture. Five related compounds can be found as impurities in the drug. We propose a HPLC method using as stationary phase a RP‐8 column eluted with different gradients of acetonitrile/phosphate buffer (pH 6) for simultaneous determination of the drug and these impurities. We also studied a high performance capillary electrophoresis (HPCE) method for quality control of fenticonazole. The separation of fenticonazole from all its impurities by HPCE was obtained in a relative short capillary (40 cm, effective length 34 cm, 50 μm ID) with a running buffer of 30 mM phosphate (pH 3) containing 8 mM trimethyl‐β‐cyclodextrin. Under these experimental conditions very good separation of fenticonazole from each individual impurity is obtained in less than 20 minutes. The choice of cyclodextrin added to the running buffer was dictated by the chiral nature of fenticonazole; trimethyl‐β‐cyclodextrin is mainly used as chiral selector. The optimised HPLC and HPCE methods are compared.

In a series of homo-isoflavonoids, chloro-substituted rac-3-benzylchroman-4-ones (3 d-f) showed an antiviral in vitro activity against selected picornaviruses. In order to study the anti-rhinovirus activity of each stereoisomer, racemic mixtures of 3 d and 3 e were successfully resolved by high-performance liquid chromatography, using a Whelk-O 1 column as chiral stationary phase. The CD spectra confirm that the two eluates of each compound are enantiomers but do not allow the assignment of their absolute configurations. The antiviral activity of the isomers and their racemates was tested in vitro against human rhinovirus serotype 1B and 14 infection, by means of the plaque reduction assay. All homoisoflavonoids tested exhibited an inhibitory effect on rhinovirus replication with an activity depending on virus serotype and compound. The two enantiomers of each compound and the corresponding racemate were equipotent, clearly showing that the configuration of the chiral center in position 3 does not influence the activity against both rhinovirus serotypes. Chirality 11:495–500, 1999.© 1999 Wiley-Liss, Inc.

In a series of homo‐isoflavonoids, chloro‐substituted rac‐3‐benzylchroman‐4‐ones (3 d‐f)showed an antiviral in vitro activity against selected picornaviruses. In order to study the anti‐rhinovirus activity of each stereoisomer, racemic mixtures of 3 dand 3 ewere successfully resolved by high‐performance liquid chromatography, using a Whelk‐O 1 column as chiral stationary phase. The CD spectra confirm that the two eluates of each compound are enantiomers but do not allow the assignment of their absolute configurations. The antiviral activity of the isomers and their racemates was tested in vitro against human rhinovirus serotype 1B and 14 infection, by means of the plaque reduction assay. All homoisoflavonoids tested exhibited an inhibitory effect on rhinovirus replication with an activity depending on virus serotype and compound. The two enantiomers of each compound and the corresponding racemate were equipotent, clearly showing that the configuration of the chiral center in position 3 does not influence the activity against both rhinovirus serotypes. Chirality 11:495–500, 1999.© 1999 Wiley‐Liss, Inc.

The 3-benzyl-2H-chromenes (3 a-d), designed as potential inhibitors of picornavirus infections, were synthesized by a simple and convenient three-step procedure starting from the O-alkylation of the appropriate 2-(hydroxymethyl)phenols with 1-bromo-3-phenylpropan-2-ones. The resulting ethers (1 a-d) were converted to the corresponding triphenylphosphonium bromides (2 a-d) and finally cyclized by an intramolecular Wittig reaction.

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