Synthesis, structural characterization and antimicrobial activity of new macrocyclic ligands and their transition metal complexes

Abstract

Aza-oxo-thia makrosiklik ligandlardan yeni iki seri; 1,3,5,11,13,15-hexaaza-6,10,16,20-tetraoxo-8,18-dithia-2,3,4:12,13,14-dipyridine cyclocosane (PDAC1S1), 1,3,5,12,14,16-hexeaza-6,11,17,22-tetraoxo-8,9,19,20-tetrathia-2,3,4:13,14,15-dipyri- dine cyclodocosane (PDAC1S2), 1,3,5,13,15,17-hexaaza-6,12,18,24-tetraoxo-9,21-dithia-2,3,4:14,15,16- dipyridine cyclotetracosane (PDAC2S1), 1,3,5,14,16,18-hexaaza-6,13,19,26-tetraoxo-9,10,22,23-tetrathia-2,3,4:15,16,17-dipyridine cyclohexacosane (PDAC2S2), 2,4,6,9,12,14,16,19-octaaza-1,7,11,17-tetraoxo-3,4,5:8,9,10:13,14,15:18, 19,20-tetrapyridine cyclocosane (PDAPCA), 2,6,12,16-tetraaza-1,7,11,17-tetraoxo-9,19-dithia-[(4?-methyl-5?,4,3?)(14?-methyl-15?,14,13?)]-ditriazine cyclocosane (DAMTAC1S1), 2,6,13,17-teraaza-1,7,12,18-tetraoxo-9,10,20,21-tetrathia-[(4?-methyl-5?,4,3?)(15?-methyl-14?,16?,15)] ditriazine cyclodocosane (DAMTAC1S2), 2,6,14,18-tetraaza-1,7,13,19-tetraoxo-10,22-dithia-[(4?-methyl-5?,3?,4)(16?- methyl-15?,17?,16)] di-triazine cyclotetracosane (DAMTAC2S1), 2,6,15,19-tetraaza-1,7,14,12-tetraoxo-10,11,23,24-tetrathia-[(4?-methyl-5?,4,3?)(17?-methyl-8?,17,16?)] ditriazine cyclo-hexacosane (DAMTAC2S2) ve (PDAPCA) ligandının çinko halidler ZnX2 (X = Cl, Br, I) ile monometalik komleksleri sentezlendi. Ligandlar ve kompleksler elemental analiz, iletkenlik ölçümleri, FT-Raman, FT-IR, 1H and 13C NMR spektroskopi yöntemleri kullanılarak yapısal olarak karakterize edildi. Antimikrobial ve antifungal aktiviteleri birçok bakteri ve mantar kültürüne karşı disk difüzyon ve minimum inhibisyon konsantrasyonu (MIC) metodları kullanılarak tayin edildi. Disk difüzyon metodundan elde edilen sonuçlar bilinen antibakteriyellerden Penicilin-G, Ampicilin, Cefotaxime, Vancomycin, Oflaxacin ve Tetracyclin ile tek tek karşılaştırıldı. Minumum inhibisyon konsantrasyon metodundan elde edilen sonuçlar antibakteriyel olarak Gentamycin ve antifungal olarak Nystatin ile karşılaştırıldı. Antifungal aktiviteler Candida albicans, Kluyveromyces fragilis, Rhodotorula rubra, Debaryomyces hansenii, ve Hanseniaspora guilliermondii olarak adlandırılan beş mantar kültürü üzerinde çalışılarak rapor edildi, sonuçlar ticari antifungallardan Nystatin, Ketaconazole ve Clotrimazole referans alınarak elde edildi.

Two new series of new mixed aza-oxo-thia macrocyclic ligands; 1,3,5,11,13,15-hexaaza-6,10,16,20-tetraoxo-8,18-dithia-2,3,4:12,13,14-dipyridinecyclocosane (PDAC1S1); 1,3,5,12,14,16-hexeaza-6,11,17,22-tetraoxo-8,9,19,20-tetrathia-2,3,4:13,14 15-dipyridine cyclodocosane (PDAC1S2); 1,3,5,13,15,17-hexaaza-6,12,18,24-tetraoxo-9,21-dithia- 2,3,4:14,15,6- dipyridine cyclotetracosane(PDAC2S1); 1,3,5,14,16,18-hexa -aza-6,13,19,26-tetraoxo-9,10,22,23-tetrathia-2,3,4:15,16,17-dipyridine cyclohexaco-sane (PDAC2S2); 2,4,6,9,12,14,16,19-octaaza-1,7,11,17-tetraoxo-3,4,5:8,9,10:13,14,15: 18,19,20-tetrapyridine cyclocosane (PDAPCA); 2,6,12,16-tetraaza-1,7,11,17-tetraoxo-9,19-thia-[(4?-methyl-5?,4,3?) (14?-methyl-15?,14,13?)]-ditriazine cyclocosane (DAMTA C1S1); 2,6,13,17-teraaza-1,7,12,18-tetraoxo-9,10,20,21-tetrathia-[(4?-methyl-5?,4,3?)(15?-methyl-14?,16?,15)] ditriazine cyclodocosane (DAMTAC1S2); 2,6,14,18-tetraaza-1,7,13,19-tetraoxo-10,22-dithia-[(4?-methyl-5?,3?,4)(16?- methyl-15?,17?,16)] ditriazine cyclotetracosane (DAMTAC2S1); 2,6,15,19-tetraaza-1,7,14,12-tetraoxo-10,11,23,24-tetrathia [(4?-methyl-5?,4,3?)(17?-methyl-8?,17,16?)] ditriazine cyclohexacosane (DAMTAC2S2) and monometallic complexes of (PDAPCA) ligand with zinc halides ZnX2 (X = Cl, Br, I) were synthesized. The structural features of these ligands and the complexes have been studied by elemental analysis, conductivity measurements, FT-Raman, FT-IR, 1H and 13C NMR spectroscopy. The antimicrobial and antifungal activities of the ligands and complexes were evaluated using disk diffusion method as well as the minimal inhibitory concentration (MIC) dilution method, against several bacteria and yeast cultures. The obtained results from disk diffusion method were assessed in side-by-side comparison with those of Penicilin-G, Ampicilin, Cefotaxime, Vancomycin, Oflaxacin and Tetracyclin well known antibacterial agents. The results from dilution procedure were compared with Gentamycin as antibacterial and Nystatin as antifungal. The antifungal activities are reported on five yeast cultures namely Candida albicans, Kluyveromyces fragilis, Rhodotorula rubra, Debaryomyces hansenii, and Hanseniaspora guilliermondii, and the results are referenced with Nystatin, Ketaconazole, and Clotrimazole, commercial antifungal agents.