5-Carba-pterocarpens: A new scaffold with anti-HCV activity.
The synthesis of a series of 5-carba-pterocarpens derivatives involving the cyclization of α-aryl-α-tetralones is described. Several compounds demonstrated potent activity and selectivity in vitro against HCV replicon reporter cells. The best profile in Huh7/Rep-Feo1b replicon reporter cells was observed with 2h (EC50 = 5.5 μM/SI = 20), while 2e was the most active in Huh7.5-FGR-JC1-Rluc2A replicon reporter cells (EC50 = 1.5 μM/SI = 70). Hydroxy groups at A- and D-rings are essential for anti-HCV activity, and substitutions in the A-ring at positions 3 and 4 resulted in enhanced activity of the compounds.
['Fernandes|Talita de A|TA|', 'Manvar|Dinesh|D|', 'Domingos|Jorge L O|JLO|', 'Basu|Amartya|A|', 'Nichols|Daniel Brian|DB|', 'Kaushik-Basu|Neerja|N|', 'Costa|Paulo R R|PRR|']
D000840:Anisoles D000998:Antiviral Agents D002384:Catalysis D002460:Cell Line D006146:Guanidines D016174:Hepacivirus D006526:Hepatitis C D006801:Humans D010165:Palladium D012093:Replicon D044024:Tetralones
BBr(3) mediated demethylation-cyclization Carba-pterocarpens Hepatitis C virus inhibitors Microwave irradiation Palladium catalyzed arylation