| Summary: | A series of novel substituted 1-<i>O</i>-alkylglycerols (AKGs) containing methoxy (<b>8</b>), <i>gem</i>-difluoro (<b>9</b>), azide (<b>10</b>) and hydroxy (<b>11</b>) group at 12 position in the alkyl chain were synthesized from commercially available ricinoleic acid (<b>12</b>). The structures of these new synthesized AKGs were established by NMR experiments as well as from the HRMS and elementary analysis data. The antimicrobial activities of the studied AKGs <b>8</b>–<b>11</b> were evaluated, respectively, and all compounds exhibited antimicrobial activity to different extents alone and also when combined with some commonly used antibiotics (gentamicin, tetracycline, ciprofloxacin and ampicillin). AKG <b>11</b> was viewed as a lead compound for this series as it exhibited significantly higher antimicrobial activity than compounds <b>8</b>–<b>10</b>.
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