Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 23, Issue 24, Pages 6563-6568Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2013.10.069
Keywords
Riccardin; Isoplagiochin; Marchantin; Methicillin resistance; Structure-activity relationship
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Funding
- Drug Discovery for Intractable Infectious Diseases Project, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
- Uehara Memorial Foundation
- Ministry of Education, Culture, Sports, Science and Technology (MEXT) [25460157]
- MEXT Supported Program for the Strategic Research Foundation at Private Universities
- Grants-in-Aid for Scientific Research [25460157] Funding Source: KAKEN
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We synthesized a series of macrocyclic bis(bibenzyl) derivatives, including riccardin-, isoplagiochin- and marchantin-class structures, and evaluated their antibacterial activity towards methicillin-resistant Staphylococcus aureus (anti-MRSA activity). The structure-activity relationships and the results of molecular dynamics simulations indicated that bis(bibenzyl)s with potent anti-MRSA activity commonly have a 4-hydroxyl group at the D-benzene ring and a 2-hydroxyl group at the C-benzene ring in the hydrophilic part of the molecule, and an unsubstituted phenoxyphenyl group in the hydrophobic part of the molecule containing the A-B-benzene rings. Pharmacological characterization of the bis(bibenzyl) derivatives and 2-phenoxyphenol fragment 25, previously proposed as the minimum structure of riccardin C 1 for anti-MRSA activity, indicated that they have different action mechanisms: the bis(bibenzyl) s are bactericidal, while 25 is bacteriostatic, showing only weak bactericidal activity. (C) 2013 Elsevier Ltd. All rights reserved.
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