Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 18, Issue 1, Pages 104-108Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2007.11.003
Keywords
bromophenol; red alga; structure-activity relationship; antimicrobial
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A series of bromophenols was obtained by isolation from red alga Odonthalia corymbifera and by reactions of bis(hydroxyphenyl)methanes with bromine. New bromophenols including 3,3,5,5'-tetrabromo-2,2',4,4'-tetrahydroxydiphenylmethane (10), a regioisomer of the potent antimicrobial natural product, together with known derivatives were synthesized in high yield. All of the isolated and synthesized compounds were tested for antimicrobial activity against Gram-negative, Gram-positive bacteria and fungi. The preliminary structure-activity relationship, to elucidate the essential structure requirements for antimicrobial activity, has been described. Among the isolated natural products 2,2',3,3'-tetrabromo-4,4',5,5'-tetrahydroxydiphenylmethane (4) was found to be the most active derivative against Candida albicans, Aspergillus fumigatus, Trichophyton rubrum, and Trichophyton mentagrophytes. The synthetic bromophenols 3,3'-dibromo-6,6'-dihydroxydiphenylmethane (13) and 3,3',5,5'-tetrabromo-6, 6'-dihydroxydiphenylmethane (14) showed potent antibacterial effect against Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus. Proteus vulgaris, and Salmonella typhimurium. (C) 2007 Elsevier Ltd. All rights reserved.
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