title: Synthesis and antiviral activity of maleopimaric and quinopimaric acids' derivatives.
abstract: A series of maleopimaric and quinopimaric acids' derivatives modified in the E-ring, at the carbonyl- and carboxyl-groups were synthesized and evaluated for their activity in vitro against respiratory viruses (influenza; rhinovirus; adenovirus; and SARS), papilloma virus, and hepatitis B and C viruses. The antiviral screening of levopimaric acid diene adducts derivatives was carried out with minimal effect on SARS and influenza type B viruses. Excellent antiviral activity of the ozonolysis product of maleopimaric acid and dihydroquinopimaric methyl-(2-methoxycarbonyl)ethylene amide was found toward papilloma virus (HPV-11 strain) with the selectivity index of SI 30 and 20, respectively. Methyl (2-methoxycarbonyl)ethylene-, 1β-hydroxy-5'-kaprolaktamo- and 4β-hydroxy-4α,14α-epoxy-13(15)-ene-dihydroquinopimaric acid derivatives have also shown activity against replication of HCV nucleic acid and low toxicity.
authors.affiliation: Institute of Petrochemistry and Catalysis of the Russian Academy of Sciences, 141 Prospect Oktyabrya, 450075 Ufa, Russian Federation. Electronic address: tretyakovaelv@gmail.com.
authors.forename: Elena V
authors.initials: EV
authors.lastname: Tretyakova
authors.affiliation: Ufa Institute of Chemistry of the Russian Academy of Science, 71 Prospect Oktyabrya, 450054 Ufa, Russian Federation.
authors.forename: Irina E
authors.initials: IE
authors.lastname: Smirnova
authors.affiliation: Institute of Petrochemistry and Catalysis of the Russian Academy of Sciences, 141 Prospect Oktyabrya, 450075 Ufa, Russian Federation.
authors.forename: Elena V
authors.initials: EV
authors.lastname: Salimova
authors.affiliation: Institute of Petrochemistry and Catalysis of the Russian Academy of Sciences, 141 Prospect Oktyabrya, 450075 Ufa, Russian Federation.
authors.forename: Victor N
authors.initials: VN
authors.lastname: Odinokov
mesh_terms: D045784:Abietanes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014780:Viruses / Q000187:drug effects*
chemical_list: D045784:Abietanes; D000998:Antiviral Agents; D014315:Triterpenes; C542630:dihydroquinopymaric acid; C027815:maleopimaric acid
keywords: Antiviral activity; Diterpenes; Levopimaric acid; Maleopimaric acid; Quinopimaric acid; Synthesis