Synthesis, characterization and determination of antimicrobial activities of new triazole derivatives based on calix[4]arene

This study includes synthesis of new calix[4]arene macromolecules with triazole derivatives and determination of their antimicrobial activities. The structures of the synthesized compounds were elucidated using spectroscopic methods (FT-IR, 1 H-NMR, 13 C-NMR, MS, Elemental Analysis). In synthesis studies, 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrahydroxycalix[4]arene (1) was first synthesized using methods known in the literatüre. According to another method known in the literature, 5,11,17,23-Tetra-tert-butyl-25,27-bis(but-3-ynyloxy)-26,28-dihydroxycalix[4]arene (2) compound containing a terminal alkyne group was synthesized by interacting with 4-bromo-1-butyne in the presence of K2CO3 in the acetone as a solvent. Afterwards, aryl halides are converted to aryl azides in the presence of NaN3 in the DMF as a solvent, according to the methods in the literatüre; benzyl azide (3a); 2,3,4,5,6-pentafluorobenzyl azide (3b); 4-nitrobenzyl azide (3c); 2-(azidomethyl) naphthalene (3d). Compound having terminal alkyne groups (2) and (3a-d) aryl azides derivates were synthesized by subjecting them to copper-catalyzed click reactions and new triazole derivatives of compounds (4a-d) were obtained. To determine the antimicrobial activities of synthesized (4a-d) novel triazole derived calix[4]arene macromolecules, Pseudomonas aeruginosa ATCC 11778, Escherichia coli ATCC 35213, Staphylococcus aureus ATCC 12600, Streptococcus mutans ATCC 10449 were used as test microorganisms. In line with the findings obtained, at maximum concentration (8 mg/mL), (4a) Streptococcus mutans ATCC 10449; (4c) Pseudomonas aeruginosa ATCC 11778, Streptococcus mutans ATCC 10449; (4d) Pseudomonas aeruginosa ATCC 11778, Escherichia coli ATCC 35213 and Streptococcus mutans ATCC 10449 it was determined that it has antimicrobial activity as much as the positive control (ofloxacin) against it.