Ki-Bong Oh, Ji Hye Lee, Soon-Chun Chung
2008
Citations
0
Influential Citations
125
Citations
Quality indicators
Journal
Bioorganic & medicinal chemistry letters
Abstract
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.