Synthesis and antimicrobial evaluation of novel analogues of dehydroabietic acid prepared by CH-Activation

Martin Berger; Alexander Roller; Nuno Maulide

doi:10.1016/j.ejmech.2016.12.012

Synthesis and antimicrobial evaluation of novel analogues of dehydroabietic acid prepared by CH-Activation

Eur J Med Chem. 2017 Jan 27:126:937-943. doi: 10.1016/j.ejmech.2016.12.012. Epub 2016 Dec 9.

Authors

Martin Berger¹, Alexander Roller², Nuno Maulide³

Affiliations

¹ Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria.
² Center of X-ray Structure Analysis, University of Vienna, Währinger Straße 42, 1090 Vienna, Austria.
³ Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria. Electronic address: nuno.maulide@univie.ac.at.

PMID: 27997880
DOI: 10.1016/j.ejmech.2016.12.012

Abstract

Dehydroabietic acid (DHAA) plays an important role in drug discovery. Its modification at chemically reactive positions has been exploited to a large extent over the last decades, generating a wide range of analogues. In contrast, introduction of substituents at chemically inert positions remains a sizeable challenge. Hereby we wish to report the synthesis of a first series of C-19-arylated DHAA-analogues by application of a simple CH activation protocol, as well as their antimicrobial activity against methicillin resistant Staphylococcus aureus (MRSA).

Keywords: Antimicrobial; CH-activation; Dehydroabietic acid; Directing group; MRSA.

MeSH terms

Abietanes / chemical synthesis*
Abietanes / chemistry
Abietanes / pharmacology*
Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Chemistry Techniques, Synthetic
Drug Design*
Drug Evaluation, Preclinical
Methicillin-Resistant Staphylococcus aureus / drug effects

Substances

Abietanes
Anti-Bacterial Agents
dehydroabietic acid

Grants and funding

W 1232/FWF_/Austrian Science Fund FWF/Austria