title: 5-Carba-pterocarpens: A new scaffold with anti-HCV activity.
abstract: 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.
authors.affiliation: Laboratório de Química Bioorgânica, Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Bloco H, Ilha da Cidade Universitária, 21941-590 Rio de Janeiro, RJ, Brazil.
authors.forename: Talita de A
authors.initials: TA
authors.lastname: Fernandes
authors.affiliation: Department of Microbiology, Biochemistry and Molecular Genetics, New Jersey Medical School, Rutgers-The State University of New Jersey, 185 South Orange Avenue, New Jersey 07103, USA.
authors.forename: Dinesh
authors.initials: D
authors.lastname: Manvar
authors.affiliation: Departamento de Química Orgânica, Centro de Tecnologia e Ciências, Universidade do Estado do Rio de Janeiro, Rua São Francisco Xavier 524, Pav. Haroldo Lisboa da Cunha - s 406 - Maracanã, 20550-900 Rio de Janeiro, RJ, Brazil.
authors.forename: Jorge L O
authors.initials: JLO
authors.lastname: Domingos
authors.affiliation: Department of Microbiology, Biochemistry and Molecular Genetics, New Jersey Medical School, Rutgers-The State University of New Jersey, 185 South Orange Avenue, New Jersey 07103, USA.
authors.forename: Amartya
authors.initials: A
authors.lastname: Basu
authors.affiliation: Department of Biological Sciences, Seton Hall University, 400 South Orange Avenue, New Jersey, 07079, USA.
authors.forename: Daniel Brian
authors.initials: DB
authors.lastname: Nichols
authors.affiliation: Department of Microbiology, Biochemistry and Molecular Genetics, New Jersey Medical School, Rutgers-The State University of New Jersey, 185 South Orange Avenue, New Jersey 07103, USA. Electronic address: kaushikbasu.neerja@gmail.com.
authors.forename: Neerja
authors.initials: N
authors.lastname: Kaushik-Basu
authors.affiliation: Laboratório de Química Bioorgânica, Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Bloco H, Ilha da Cidade Universitária, 21941-590 Rio de Janeiro, RJ, Brazil. Electronic address: prrcosta2011@gmail.com.
authors.forename: Paulo R R
authors.initials: PRR
authors.lastname: Costa
mesh_terms: D000840:Anisoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002384:Catalysis; D002460:Cell Line; D006146:Guanidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D016174:Hepacivirus / Q000187:drug effects* / Q000235:genetics; D006526:Hepatitis C / Q000188:drug therapy / Q000821:virology; D006801:Humans; D010165:Palladium / Q000737:chemistry; D012093:Replicon / Q000187:drug effects; D044024:Tetralones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000840:Anisoles; D000998:Antiviral Agents; D006146:Guanidines; D044024:Tetralones; C006921:dodine; D010165:Palladium
keywords: BBr(3) mediated demethylation-cyclization; Carba-pterocarpens; Hepatitis C virus inhibitors; Microwave irradiation; Palladium catalyzed arylation