Synthesis and antimicrobial activities of halogenated bis(hydroxyphenyl)methanes.
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 Candidaalbicans, Aspergillusfumigatus, Trichophytonrubrum, and Trichophytonmentagrophytes while 3,3',5,5'-tetrachloro-2,2'-dihydroxydiphenylmethane (18) exerted a powerful antibacterial effect against Staphylococcusaureus, Bacillussubtilis, Micrococcusluteus, Proteusvulgaris, and Salmonellatyphimurium.
Oh
Ki-Bong
KB
Department of Agricultural Biotechnology, Seoul National University, Seoul 151-921, Republic of Korea.
Lee
Ji Hye
JH
Lee
Jong Wook
JW
Yoon
Kyung-Mi
KM
Chung
Soon-Chun
SC
Jeon
Heung Bae
HB
Shin
Jongheon
J
Lee
Hyi-Seung
HS
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D002733:Chlorophenols / Q000737:chemistry; D015195:Drug Design; D006219:Halogens / Q000737:chemistry; D008697:Methane / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D008956:Models, Chemical; D019800:Phenol / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D002733:Chlorophenols; D006219:Halogens; D010636:Phenols; D019800:Phenol; D008697:Methane