Synthesis and antiviral activity of 7-O-(omega-substituted)-alkyl-3-O-methylquercetin derivatives.
3',4'-Di-O-benzyl-3-O-methylquercetin (2), the precursor in the synthesis of an important antivirally active flavone 3-O-methylquercetin (1), was regioselectively alkylated at the 7-OH position by a series of 1,omega-dihaloalkanes and omega-bromoalkanols. Dimerization of the flavone had to be avoided by applying strict reaction conditions. Subsequent debenzylation was carried out by catalytic transfer hydrogenolysis, affording quantitatively the 7-O-(omega-haloalkyl)-3-O-methylquercetin (11-14) and 7-O-(omega-hydroxyalkyl)-3-O-methylquercetin derivatives (15, 16). All compounds were tested for their antiviral activity against poliomyelitis- and HIV-viruses.
Boers
F
F
Department of Chemistry, University of Antwerp (RUCA), Belgium.
Lemiere
G
G
Lepoivre
J A
JA
De Groot
A
A
Dommisse
R
R
De Bruyne
T
T
Vlietinck
A J
AJ
Vanden Berghe
D A
DA
D000818:Animals; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002522:Chlorocebus aethiops; D006678:HIV / Q000187:drug effects*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D017955:Poliovirus / Q000187:drug effects*; D011794:Quercetin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D014709:Vero Cells
D019380:Anti-HIV Agents; D000998:Antiviral Agents; D011794:Quercetin