Potansiyel biyolojik aktif bazı yeni N-(3-alkil/aril-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il)-amid türevlerinin sentezi, karakterizasyonu ve bazı özelliklerinin incelenmesi

Abstract

Bu çalışmada, öncelikli olarak çalışma için gerekli olan 9 adet 3-alkil(aril)-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on bileşikleri sentezlenmiştir. Daha sonra, sentezlenen amin bileşiklerinin 3-nitrobenzoil klorür, suksinil klorür, okzaloil klorür, tereftaloil klorür, pivaloil klorür ve 3-metoksibenzoil klorür ile n-butil asetatlı ortamda ayrı ayrı reaksiyonundan sırasıyla N-[3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il]-3-nitrobenzamid, N,N'-di[3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il]-suksinamid, N,N'-di[3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il]-okzalamid, N,N'-di[3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il]-tereftalamid, N-[3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il]-3-pivalamid ve N-[3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il]-3-metoksibenzamid bileşikleri sentezlenmiştir. Sentez bölümünün devamında; Mannich reaksiyonu uyarınca, formaldehit varlığında, elde edilen N-[3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il]-3-nitrobenzamid, N,N'-di[3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il]-suksinamid ve N,N'-di[3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il]-tereftalamid bileşiklerinin morfolin ile reaksiyonundan 4 adet yeni N-[1-(morfolin-4-il-metil)-3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il]-3-nitrobenzamid bileşikleri, 3 adet yeni N,N'-di[1-(morfolin-4-il-metil)-3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il]-suksinamid bileşikleri ve son olarak 3 adet yeni N,N'-di[1-(morfolin-4-il-metil)-3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il]-tereftalamid bileşikleri elde edilmiştir.Çalışmanın ikinci bölümde, sentezlenen 52 yeni bileşiğin yapıları IR, 1H-NMR ve 13C-NMR spektroskopik yöntemleri kullanılarak aydınlatılmıştır.Çalışmanın üçüncü bölümünde; indirgeme gücü, serbest radikal giderme aktivitesi ve metal şelat aktivitesi yöntemleri kullanılarak sentezlenen yeni amid türevi ve Mannich bazı bileşikleri in-vitro antioksidan özellikleri incelenmiş ve elde edilen sonuçlar kullanılan standart antioksidan bileşikler ile karşılaştırılmıştır.Çalışmanın dördüncü bölümünde; elde edilen yeni bileşiklerin in-vitro antimikrobiyal özellikleri agar kuyucuk yöntemi ile 5 farklı mikroorganizmaya (Bacillus cereus, Klebsiella pneumoniae, Staphylococcus aureus, Serratia marcescens ve Candia albicans) karşı incelenmiş olup elde edilen sonuçlar değerlendirilmiştir.

In this study, nine 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-one compounds which are primarily required for the study were synthesized. Subsequent reaction of the synthesized amine compounds with 3-nitrobenzoyl chloride, succinyl chloride, oxalyl chloride, terephthaloyl chloride, pivaloly chloride and 3-methoxhybenzoyl chloride in n-butyl acetate were synthesized N-[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-3-nitrobenzamide, N,N'-di[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-succinamide, N,N'-di[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-oxalamide, N,N'-di[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-terephthalamide N-[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-pivalamide and N-[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-3-metoxybenzamide compounds, respectively. In the continuation of the synthesis section; according to the Mannich reaction, in the presence of formaldehyde, the reaction of N-[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-3-nitrobenzamide, N,N'-di[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-succamide and N,N'-di[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-terephthalamide compounds with morpholine 4 new N-[1-(morpholin-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-3-nitrobenzamide compounds, 3 new N,N'-di[1-(morpholin-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-succamide compounds and finally 3 new N,N'-di[1-(morpholin-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-terephthalamide compounds were obtained.In the second section of the study, structures of the synthesized 52 new compounds were characterized by using IR, 1H NMR, 13C NMR spectroscopic methods.In the third section of the study, in-vitro antioxidant activities of synthesized new amide derivatives and Mannich bases were investigated by using reducing power, free radical scavenging and metal chelating activity and results of the study were compared with standard antioxidant compounds.In the fourth section of the study, antimicrobial properties of new compounds were investigated against five different microorganisms (Bacillus cereus, Klebsiella pneumoniae, Staphylococcus aureus, Serratia marcescens ve Candia albicans) with agar well diffusion method and the obtained results were evaluated.