Molecular design of anti-MRSA agents based on the anacardic acid scaffold.
A series of anacardic acid analogues possessing different side chains viz. phenolic, branched, and alicyclic were synthesized and their antibacterial activity tested against methicillin-resistant Staphylococcus aureus (MRSA). The maximum activity against this bacterium occurred with the branched side-chain analogue, 6-(4',8'-dimethylnonyl)salicylic acid, and the alicyclic side-chain analogue, 6-cyclododecylmethyl salicylic acid, with the minimum inhibitory concentration (MIC) of 0.39 microg/mL, respectively. This activity was superior to that of the most potent antibacterial anacardic acid isolated from the cashew Anacardium occidentale (Anacardiaceae), apple and nut, that is, the 6-[8'(Z),11'(Z),14'-pentadecatrienyl]salicylic acid.
Green
Ivan R
IR
Department of Chemistry, University of the Western Cape, Bellville 7530, South Africa. igreen@uwc.ac.za
Tocoli
Felismino E
FE
Lee
Sang Hwa
SH
Nihei
Ken-Ichi
K
Kubo
Isao
I
D048729:Anacardic Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D031021:Anacardium / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015195:Drug Design; D027845:Malus / Q000737:chemistry; D008712:Methicillin / Q000494:pharmacology; D016106:Methicillin Resistance; D008826:Microbial Sensitivity Tests; D009754:Nuts / Q000737:chemistry; D013211:Staphylococcus aureus / Q000187:drug effects*; D013329:Structure-Activity Relationship
C523644:6-(4',8',14'-pentadecatrienyl)salicylic acid; C523643:6-(4',8'-dimethylnonyl)salicylic acid; D048729:Anacardic Acids; D000900:Anti-Bacterial Agents; C088115:anacardic acid; D008712:Methicillin