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: Elena V Tretyakova, Irina E Smirnova, Elena V Salimova, Victor N Odinokov
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 23 Issue 20 Pg. 6543-50 (Oct 15 2015) ISSN: 1464-3391 [Electronic] England
• PMID: 26372075 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Review)
• Copyright: Copyright © 2015 Elsevier Ltd. All rights reserved.

Chemical References

• Abietanes
• Antiviral Agents
• Triterpenes
• dihydroquinopymaric acid
• maleopimaric acid

Topics

• Abietanes (chemical synthesis, chemistry, pharmacology)
• Antiviral Agents (chemical synthesis, chemistry, pharmacology)
• Microbial Sensitivity Tests
• Molecular Structure
• Structure-Activity Relationship
• Triterpenes (chemical synthesis, chemistry, pharmacology)
• Viruses (drug effects)