Total synthesis of acylphloroglucinols and their antibacterial activities against clinical isolates of multi-drug resistant (MDR) and methicillin-resistant strains of Staphylococcus aureus

Article


Rahman, M., Shiu, Winnie K.P., Gibbons, Simon and Malkinson, John P. 2018. Total synthesis of acylphloroglucinols and their antibacterial activities against clinical isolates of multi-drug resistant (MDR) and methicillin-resistant strains of Staphylococcus aureus. European Journal of Medicinal Chemistry. 155, pp. 255-262. https://doi.org/10.1016/j.ejmech.2018.05.038
AuthorsRahman, M., Shiu, Winnie K.P., Gibbons, Simon and Malkinson, John P.
Abstract

Bioassay-directed drug discovery efforts focusing on various species of the genus Hypericum led to the discovery of a number of new acylphloroglucinols including (S,E)-1-(2-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-4,6-dihydroxyphenyl)-2-methylbutan-1-one (6, olympicin A) from H. olympicum, with MICs ranging from 0.5 to 1 mg/L against a series of clinical isolates of multi-drug-resistant (MDR) and methicillin-resistant Staphylococcus aureus (MRSA) strains. The promising activity and interesting chemistry of olympicin A prompted us to carry out the total synthesis of 6 and a series of analogues in order to assess their structure-activity profile as a new group of antibacterial agents. Following the synthesis of 6 and structurally-related acylphloroglucinols 7–15 and 18–24, their antibacterial activities against a panel of S. aureus strains were evaluated. The presence of an alkyloxy group consisting of 8–10 carbon atoms ortho to a five-carbon acyl substituent on the phloroglucinol core are important structural features for promising anti-staphylococcal activity.

JournalEuropean Journal of Medicinal Chemistry
Journal citation155, pp. 255-262
ISSN0223-5234
Year2018
PublisherElsevier
Accepted author manuscript
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Digital Object Identifier (DOI)https://doi.org/10.1016/j.ejmech.2018.05.038
Web address (URL)https://doi.org/10.1016/j.ejmech.2018.05.038
Publication dates
Online25 May 2018
Print15 Jul 2018
Publication process dates
Deposited29 May 2018
Accepted24 May 2018
Accepted24 May 2018
FunderHeptagon Fund
Copyright information© 2018 Elsevier
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