Hetero halkalı bazı yeni bileşiklerin biyolojik aktivitelerinin incelenmesi

Abstract

Bu tez çalışmasında, öncelikle 3-alkil(aril)-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on bileşikleri elde edilmiştir. 4-Hidroksi-3-metoksibenzaldehid ile trietilamin varlığında benzoil klorür ile reaksiyonundan elde edilen 4-formil-2-metoksifenil benzoat ile sentezlenen bu bileşikler reaksiyona sokularak 6 adet literatürde kayıtlı 4-(3-alkil/aril-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il-azometin)-2-metoksifenil benzoat bileşikleri sentezlenmiştir.Tez çalışmasının orjinal bölümünde, 4-(3-alkil/aril-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il-azometin)-2-metoksifenil benzoat'ların formaldehit varlığında morfolin ve 2,6-dimetilmorfolin ile reaksiyonundan karşın gelen yeni 4-[1-(morfolin-4-il-metil)-3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il-azometin]-2-metoksifenil benzoat ve 5 adet yeni 4-[1-(2,6-dimetilmorfolin-4-il-metil)-3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il-azometin]-2-metoksifenil benzoat bileşikleri elde edilmiştir. 12 Adet yeni sentezlenen heterosiklik bileşiklerin yapıları IR, 13C-NMR ve 1H-NMR spektroskopik metotları ile karakterize edilmiştir.Çalışmada üçüncü olarak elde edilen yeni 4-[1-(morfolin-4-il-metil)-3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il-azometin]-2-metoksifenil benzoat ve yeni 4-[1-(2,6-dimetilmorfolin-4-il-metil)-3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il-azometin]-2-metoksifenil benzoat'ların metal şelat, indirgeme gücü ve serbest radikal giderme aktivitesi metotları kullanılarak in-vitro antioksidan özellikleri araştırılmış ve bulunan sonuçlar tartışılmıştır. Çalışmada son olarak yeni bileşiklerin in-vitro antimikrobiyal özellikleri agar kuyucuk yöntemi ile 6 farklı mikroorganizmaya karşı incelenmiş olup elde edilen sonuçlar değerlendirilmiştir.

In this thesis, primarily 3-alkyl/aryl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones compounds were obtained. The reactions of these compounds with 4-formyl-2-methoxyphenyl benzoate which were obtained by reaction 4-hydroxy-3-methoxybenzaldehyde with benzoyl chloride in the presence triethylamine and registered in the literature six 4-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl-azomethine)-2-methoxyphenyl benzoates were synthesized.In the original part of the thesis work, 4-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl-azomethine)-2-methoxyphenyl benzoates were treated with morpholine and 2,6-dimethylmorpholine in the presence of formaldehyde according to the Mannich reaction to synthesize six novel 4-[1-(morpholin-4-yl-methyl)-3-alkyl (aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl-azomethine]-2-methoxyphenyl benzoate and six novel 4-[1-(2,6-dimethylmorpholin-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-triazol-5-on-4-yl-azomethine]-2-methoxyphenyl benzoate compunds, respectively. The structures of synthesized twelve novel heterocyclic compounds were characterized by IR, 13C-NMR and 1H-NMR spectroscopic methods.In the thirdly section of the study, the synthesized novel 4-1-(morpholin-4-yl-methyl)-3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-yl-azomethine]-2-methoxyphenyl benzoate and the novel 4-[1-(2,6-dimethylmorpholin-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-triazol-5-on-4-yl-azomethyl]-2-methoxyphenyl benzoates were investigated in vitro antioxidant properties by using free radical scavenging activity, reducing power and metal chelate activity methods and the obtained results were discussed.Finally, the new compounds were examined in-vitro antimicrobial properties against 6 different microorganisms by the agar well method and the obtained results were evaluated.