Radikal süpürücü özellik taşıyan 1,2,4-triazol-3(5)-on bileşiklerinin sentezi ve karakterizasyonu

Abstract

Bu çalışmada, 2-(3,4-dimetoksifenil) etilamin'in, bir seri ester etoksi karbonilhidrazonla (52, 53, 54, 55, 57 ve 58) reaksiyonundan yeni 6 adet, 4-(3,4-dimetoksifeniletil)-5-metil-2H-1,2,4-triazol-3(4H)-on (61), 4-(3,4-dimetoksifeniletil)-5-etil-2H-1,2,4-triazol-3(4H)-on (62), 4-(3,4-dimetoksifeniletil)-5-propil-2H-1,2,4-triazol-3(4H)-on (63), 4-(3,4-dimetoksifeniletil)-5-fenil-2H-1,2,4-triazol-3(4H)-on (64), 5-(3,4-dimetoksibenzil)-4-(3,4-dimetoksifeniletil)-2H-1,2,4-triazol-3(4H)-on (66) ve 4-(3,4-dimetoksifeniletil)-5-(tiyofen-2-il-metil)-2H-1,2,4-triazol-3(4H)-on (67) bileşiklerisentezlenmiştir. Aynıyöntemle 2-(3,4-dimetoksifenil) etilamin'in, etil p-toluat etoksikarbonil hidrazon (56) ile reaksiyonu sonucu etil N'-3,4-dimetoksifeniletilkarbomoil-4-metil benzohidrazonoat (65) bileşiği elde edilmiştir. Sentezlenen bileşiklerden birkaçıile(61, 63, 64, 66 ve 67) BBr3 reaksiyonundan katekol türevi olan 5 adet 4-(3,4-dihidroksifeniletil)-5-metil-2H-1,2,4-triazol-3(4H)-on (69), 4-(3,4-dihidroksifeniletil)-5-propil-2H-1,2,4-triazol-3(4H)-on (70), 4-(3,4-dihidroksifeniletil)-5-fenil-2H-1,2,4-triazol-3(4H)-on (71), 5-(3,4-dihidroksibenzil)-4-(3,4-dihidroksifeniletil)-2H-1,2,4-triazol-3(4H)-on (72), 4-(3,4-dihidroksifeniletil)-5-(tiyofen-2-il-metil)-2H-1,2,4-triazol-3(4H)-on (73)bileşiklerine ulaşılmıştır.Katekol türevi taşıyan bileşikler, DPPH ve ? ?Karoten (Linoleik Asit Oksidatifİnhibisyon) yöntemleri kullanılarak test edilmişhepside pozitif sonuçlar vermiştir.Sentezlenen orijinal nitelikte 12 adet bileşiğin yapıaydınlatılmasıIR; ¹H-NMR, ¹³C-NMR,MS, ve X-Ray (61 bileşiği için) spektroskopi yöntemleri kullanılarak yapılmıştır vesentezlere ilişkin reaksiyon mekanizmalarıönerilmiştir.Anahtar Kelimeler : Ester etoksi karbonil hidrazon, Katekol, 1,2,4-triazol-3-on, DPPH,3,4-dimetoksifeniletilamin, 3,4-dihidroksifeniletilamin,Bortribromür.

In this study, new 6 compounds 4-(3,4-dimethoxyphenethyl)-5-methyl-2H-1,2,4-triazol-3(4H)-one, 4-(3,4-dimethoxyphenethyl)-5-ethyl-2H-1,2,4-triazol-3(4H)-one, 4-(3,4-dimethoxyphenethyl)-5-propyl-2H-1,2,4-triazol-3(4H)-one, 4-(3,4-dimethoxyphenethyl)-5-phenyl-2H-1,2,4-triazol-3(4H)-one, 5-(3,4-dimethoxybenzyl)-4-(3,4-dimethoxyphenethyl)-2H-1,2,4-triazol-3(4H)-one,4-(3,4-dimethoxyphenethyl)-5-(thiophen-2yl-methyl)-2H-1,2,4-triazol-3(4H)-one were synthesizedfrom reaction 2-(3,4-dimethoxyphen) ethanamine and a series of novel ester ethoxy carbonyl hydrazones.In the same way, ethyl N?-3,4-dimethoxyphenethylcarbomoyl-4-methylbenzo hydrazonate was obtainedfrom the reaction of 2-(3,4-dimethoxyphen) ethanamine and hydrazine. Some of these compounds weretreated with BBr3 to obtain new 5 cathechol containing compounds namely,4-(3,4-dihydroxyphenethyl)-5-methyl-2H-1,2,4-triazol-3(4H)-one, 4-(3,4-dihydroxyphenethyl)-5-propyl-2H-1,2,4-triazol-3(4H)-one,4-(3,4-dihydroxyphenethyl)-5-phenyl-2H-1,2,4-triazol-3(4H)-one, 5-(3,4-dihydroxybenzyl)-4-(3,4-dimethoxyphenethyl)-2H-1,2,4-triazol-3(4H)-one and 4-(3,4-dihydroxyphenethyl)-5-(thiophen-2yl-methyl)-2H-1,2,4-triazol-3(4H)-one.Synthesis and characterization of 1,2,4-triazol-3(5)-one compounds which contain radical scaveging propertyCompounds containing catechol character were tested for their antioksidant properties employing DPPH and ?-caroten (Linoleic Acid Inhibition) assay and all of them gave pozitif results.The structure of 12 new compounds synthesized in this study were analyzed byIR, 1H-NMR, 13C-NMR, MS, X-Ray (only for compound 61) spectroscopy and reactionmechanisms were proposed for the general sythesis.Key Words: Ester ethoxy carbonyl hydrazones, catechol, 1,2,4-triazole-3-on, DPPH,3,4-dihydroxyphenethyl, 3,4-dimethoxyphenethyl, tribromo borane.