| Abstract [eng] |
With the growth of human consumption and the emerge of new bacterial and viral infections particularly important becomes the search of novel synthetic biologically active compounds. Sulfonamide and their derivatives have a wide spectrum of activity. The purpose of this work is to synthesize new biologically active acyclic and heterocyclic compounds bearing sulfonamide moieties and to investigate their chemical characteristics and biological activity. Sulfanilamide was used in synthesis of ethyl 2-[(4-sulfanilphenyl)amino]- and 2-[(2,6-dichloro-4- sulfamoylphenyl)amino]acetates and transformed into acid hydrazides. Both synthesized hydrazides were used in condensation reactions with 2,4-pentanedione and 2,5-hexanedione in the presence of catalytic hydrochloric or acetic acid to obtain pyrazole and pyrrole moieties. While reactions of acid hydrazides with aldehydes and ketones provided corresponding hydrazones. 4-[(2-Hydrazinyl-2- oxoethyl)amino]- and 3,5-dichloro-4-[(2-hydrazinyl-2-oxoethyl)amino]benzenesulfonamides were performed with phenyl isocyanate in methanol to obtain N-phenyl-{2-(2-[(4- sulfamoylphenyl)amino]acetyl}- and 2-{2-[(2,6-dichloro-4-sulfamoylphenyl)amino]acetyl}-Nphenyl-hydrazinecarbothioamides. Both synthesized hydrazinecarbothioamides were cyclized in weakly alkaline environment to provide 4-{[(4-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3- yl)methyl]amino}- and 3,5-dichloro-4-phenyl-{[(5-mercapto-4-phenyl-4H-1,2,4-triazol-3- yl)methyl]amino}benzenesulfonamides. In this work it was investigated interaction of synthesized 2-[(4-sulfonylphenyl)amino]acetic acid derivatives with eight recombinant human carbonic anhydrases (CAI, CAII, CAVB, CAVI, CAVII, CAIX, CAXII and CAXIII). This study has shown that the majority of chloro-substituted benzensulfonamides at meta- position are plausible inhibitors of carbonic anhydrases. |
