Synthesis and antimicrobial activities of halogenated bis(hydroxyphenyl)methanes |
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Authors: | Ki-Bong Oh Ji Hye Lee Jong Wook Lee Kyung-Mi Yoon Soon-Chun Chung Heung Bae Jeon Jongheon Shin Hyi-Seung Lee |
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Institution: | 1. Department of Agricultural Biotechnology, Seoul National University, Seoul 151-921, Republic of Korea;2. Center for Agricultural Biomaterials, Seoul National University, Seoul 151-921, Republic of Korea;3. Marine Natural Products Laboratory, Korea Ocean Research & Development Institute, Ansan PO Box 29, Seoul 425-600, Republic of Korea;4. Department of Chemistry, Kwangwoon University, Seoul 139-701, Republic of Korea;5. Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 151-921, Republic of Korea |
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Abstract: | A series of halophenols was prepared by the reaction of bis(hydroxyphenyl)methanes with effective halogenating agents such as bromine and sulfuryl chloride. One of these compounds, a biologically active halophenol—2,2′,3,3′-tetrabromo-4,4′,5,5′-tetrahydroxydiphenylmethane (1)—frequently isolated from red algae, was synthesized for the first time. Other halophenols included several novel compounds, together with known derivatives that were synthesized from the phenolic intermediates, bis(3,4-dihydroxyphenyl)methane (5) and bis(2-hydroxyphenyl)methane (14). All of the synthesized compounds were tested for antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. The preliminary structure–activity relationship was investigated in order to determine the essential structural requirements for their antimicrobial activity. Of all these halophenols, 2,2′,3,3′,6-pentabromo-4,4′,5,5′-tetrahydroxydiphenylmethane (8) was found to be the most active against Candida albicans, Aspergillus fumigatus, Trichophyton rubrum, and Trichophyton mentagrophytes while 3,3′,5,5′-tetrachloro-2,2′-dihydroxydiphenylmethane (18) exerted a powerful antibacterial effect against Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus, Proteus vulgaris, and Salmonella typhimurium. |
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