title: Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols including natural products.
abstract: (2-Bromo-3,4-dimethoxyphenyl) (3,4-dimethoxyphenyl)methanone (10) and its derivatives with Br, one dibromide and isomeric three tribromides, were synthesized. Demethylation of these compounds afforded a series of new bromophenols. Inhibition of human cytosolic carbonic anhydrase II (hCA II) isozyme by these new bromophenols and naturally occurring 3,4,6-tribromo-5-(2,5-dibromo-3,4-dihydroxybenzyl)benzene-1,2-diol (3), and 5,5'-methylenebis(3,4,6-tribromo-benzene-1,2-diol) (4) was investigated. The synthesized compounds showed carbonic anhydrase inhibitory capacities with IC(50) values in the range of 0.7-372 μM against hCA II. Some bromophenols investigated here showed effective hCA II inhibitory activity and might be used as leads for generating novel carbonic anhydrase inhibitors which are valuable drug candidates for the treatment of glaucoma, epilepsy, gastric and duodenal ulcers, neurological disorders, or osteoporosis.
authors.affiliation: Atatürk University, Faculty of Science, Department of Chemistry, Erzurum, Turkey.
authors.forename: Halis Türker
authors.initials: HT
authors.lastname: Balaydın
authors.forename: Hakan
authors.initials: H
authors.lastname: Soyut
authors.forename: Deniz
authors.initials: D
authors.lastname: Ekinci
authors.forename: Süleyman
authors.initials: S
authors.lastname: Göksu
authors.forename: Sükrü
authors.initials: S
authors.lastname: Beydemir
authors.forename: Abdullah
authors.initials: A
authors.lastname: Menzek
authors.forename: Ertan
authors.initials: E
authors.lastname: Sahin
mesh_terms: D001577:Benzophenones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001969:Bromobenzenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D024402:Carbonic Anhydrase II / Q000037:antagonists & inhibitors* / Q000378:metabolism; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002396:Catechols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D003600:Cytosol / Q000201:enzymology; D004305:Dose-Response Relationship, Drug; D006801:Humans; D007527:Isoenzymes / Q000037:antagonists & inhibitors / Q000378:metabolism; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D001577:Benzophenones; D001688:Biological Products; D001969:Bromobenzenes; D002257:Carbonic Anhydrase Inhibitors; D002396:Catechols; D007527:Isoenzymes; D024402:Carbonic Anhydrase II