Investigation of antimicrobial properties of p-ter-butyl calix[4]arenes tetra-functionalized from phenolic oxygen groups

This work involves the synthesis of 5,11,17,23-tetra-ter-butyl-25,26,27,28-tetrahydroxy calix[4]arene (1); 5,11,17,23-tetra-ter-butyl-25,27-bis(benzyloxy)-26,28-dihydroxy calix[4]arene (2); 5,11,17,23-tetra-ter-butyl-25,27-bis(benzyloxy)-26,28-diacetonyloxy calix[4]arene (3); 5,11,17,23-tetra-ter-butyl-25,27-bis(benzyloxy)-26,28-carbonyl methoxy calix[4]arene (4); 5,11,17,23-tetra-ter-butyl-25,27-bis-(4-nitrobenzyloxy)-26,28-dibenzyloxy calix[4]arene(5); 5,11,17,23-tetra-ter-butyl-25,27-bis-(4-aminobenzyloxy)-26,28-dibenzyloxy calix[4]arene (6) compounds and the biological activity of these compounds. In the synthesis studies, the starting compound 5,11,17,23-tetra-ter-butyl calix[4]arene 1 was synthesized according to methods described in the literature. Then, 5,11,17,23-tetra-ter-butyl-25,26,27,28-tetrahydroxycalix[4]arene (1); 5,11,17,23-tetra-ter-butyl-25,27-bisbenzyloxy-26,28-dihydroxycalix[4]arene (2); 5,11,17,23-tetra-ter-butyl-25,27-bis(benzyloxy)-26,28-diacetonyloxycalix[4]arene (3); 5,11,17,23-tetra-ter-butyl-25,27-bis(benzyloxy)-26,28-carbonylmethoxy calix[4]arene (4); 5,11,17,23-tetra-ter-butyl-25, 27-bis-(4-nitrobenzyloxy)-26,28-dibenzyloxycalix[4]arene (5); 5,11,17,23-tetra-ter-butyl-25,27-bis-(4-aminobenzyloxy)-26,28-dibenzyloxycalix[4]arene (6) were synthesized respectively, according to the methods described in the literature. Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853, Escherichia coli ATCC 35218, Bacillus subtilis and Candida glabrata were used as test microorganisms to investigate the antimicrobial activities of the synthesized compounds (1,2,3,4,5,6). At the end of the study, the most antimicrobial effect was observed against Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853, Escherichia coli ATCC 35218 and Candida glabrata for 3, 4 and 5 compounds. Keywords: Calixarene, biological activity, antimicrobial effect