Trisubstitue triazollerin sentezi, karakterizasyonu ve antioksidan aktivitelerinin incelenmesi

Abstract

Bu çalışmada, 2-(3,4-dimetoksifenil)etilamin'in, bir seri N1?açil(aril) benzo(aseto)hidrazonat'la (36, 37, 38, 39, 40, 41, 42) reaksiyonundan yeni 7 adet, 4-(3,4-dimetoksifeniletil)-3,5-dimetil-4H-1,2,4-triazol (46), 4-(3,4-dimetoksifeniletil)-3-etil-5-metil-4H-1,2,4-triazol (47), 4-(3,4-dimetoksifeniletil)-3-metil-5-(tiyofen-2-ilmetil)-4H-1,2,4-triazol (48), 4-(3,4-dimetoksifeniletil)-3,5-difenil-4H-1,2,4-triazol (49), 4-[ 4-(3,4-dimetoksifeniletil)-5-(tiyofen-2-ilmetil)-4H-1,2,4-triazol-3-il]fenol (50), 3-(4-klorofenil)-4-(3,4-dimetoksifeniletil)-5-(tiyofen-2-ilmetil)-4H-1,2,4-triazol (51) ve 4-[5-benzil-4-(3,4-dimetoksifeniletil)-4H-1,2,4-triazol-3-il]fenol (52) bileşikleri sentezlenmiştir. Aynı yöntemle 2-(3,4-dimetoksifenil) etilamin'in, etil N'-asetil-2-(4-bromofenil)asetohidrazonat (43) ile reaksiyonu sonucu N'-asetil-2-(4-bromofenil)-N-(3,4-dimetoksifenetil) asetohidrazonamit ( 53 ) bileşiği elde edilmiştir. Sentezlenen bileşiklerden birkaçı ile (49 , 50 ve 52 ) BBr3 reaksiyonundan katekol türevi olan 3 adet 4-(2-(3,5-difenil-4H-1,2,4-triazol-4-il)etil)benzen-1,2-diol ( 55 ), 4-(2-(3-(4-hidroksifenil-5-(tiyofen-2-ilmetil)-4H-1,2,4-triazol-4-il)etil)benzen-1,2-diol (56) , 4-(2-(3-benzil-5-(4-hidroksifenil)-4H-1,2,4-triazol-4-il)etil)benzen-1,2-diol ( 57 ) bileşiklerine ulaşılmıştır.Katekol türevi taşıyan bileşikler , DPPH ve ß?Karoten (Linoleik Asit Oksidatif İnhibisyon) yöntemleri kullanılarak test edilmiş , tümü pozitif sonuçlar vermiştir.Sentezlenen orijinal nitelikte 11 adet bileşiğin yapı aydınlatılması IR , ¹H-NMR , ¹³C-NMR spektroskopi yöntemleri kullanılarak yapılmıştır ve sentezlere ilişkin reaksiyon mekanizmaları önerilmiştir. In this study, new 7 compounds 4-(3,4-dimetoxyphenylethyl)-3,5-dimethyl-4H-1,2,4-triazole (46), 4-(3,4- dimetoxyphenylethyl)-3-ethyl-5-methyl-4H-1,2,4-triazole (47), 4-(3,4- dimetoxyphenylethyl)-3-methyl-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole (48), 4-(3,4-dimetoxyphenylethyl)-3,5-diphenyl-4H-1,2,4-triazole (49), 4-[4-(3,4- dimetoxyphenylethyl)-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl]phenol (50), 3-(4-chlorophenyl)-4-(3,4-dimetoxyphenylethyl)-5-( thiophen-2-ylmethyl)-4H-1,2,4-triazol (51) ve 4-[ 5-benzyl-4-(3,4- dimetoxyphenylethyl)-4H-1,2,4-triazol-3-yl]phenol (52) were synthesized from reaction 2-(3,4-dimethoxyphen) ethanamine and a series of N1?acyl(aryl) benzo(aceto)hydrazonates. In the same way, N'-acetyl-2-(4-bromophenyl)-N-(3,4-dimethoxyphenethyl) acetohydrazonamide (53) was obtained from the reaction of 2-(3,4-dimethoxyphen) ethanamine and hydrazine. Some of these compounds were treated with BBr3 to obtain new 3 cathechol containing compounds namely, 4-(2-(3,5-diphenyl-4H-1,2,4-triazol-4-yl)ethyl)benzen-1,2-diol (55), 4-(2-(3-(4-hydroxyphenyl-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-4-yl)ethyl)benzen-1,2-diol (56), 4-(2-(3-benzyl-5-(4-hydroxyphenyl)-4H-1,2,4-triazol-4-yl)ethyl)benzen-1,2-diol (57).Compounds containing catechol character were tested for their antioxidant properties employing DPPH and ß-caroten (Linoleic Acid Inhibition) assay and all of them gave pozitive results.The structure of 11 new compounds synthesized in this study were analyzed by IR, 1H-NMR and 13C-NMR spectroscopy and reaction mechanisms were proposed for the general sythesis.