4-metoksifenil ve 4-hidroksifenilünitesi taşıyan 1,2,4-triazollerin sentezi, karakterizasyonu ve biyokimyasal özelliklerinin incelenmesi
Synthesis and characterization of 1,2,4-tiazoles consisting of 4-methoxyphenyl and 4-hydroxyphenyl
Yazar: DİLEK ÜNLÜER
Danışman: DOÇ. DR. KEMAL SANCAK
Karadeniz Teknik Üniversitesi / Fen Bilimleri Enstitüsü / Kimya Ana Bilim Dalı
Derece: Yüksek Lisans, 2010
Konu: Kimya = Chemistry

Özet:
Bu çalışmada, 2-(4-metoksifenil)etilamin'in, bir seri Ester etoksi karbonil hidrazon'la (37 tipi) reaksiyonundan orijinal 9 adet, 4-(4-metoksifeniletil)-5-2H-1,2,4-triazol-3(4H)-on (51), 5-etil-4-(4-metoksifeniletil)-2H-1,2,4-triazol-3(4H)-on (52), 4-(4-metoksifeniletil)-5-propil-2H-1,2,4-triazol-3(4H)-on (53), 4-(4-metoksifeniletil)-5-(tiyofen-2-ilmetil)-2H-1,2,4-triazol-3(4H)-on (54), 5-benzil-4-(4-metoksifeniletil)-2H-1,2,4-triazol-3(4H)-on (55), 5-(4-bromobenzil)-4-(4-metoksifeniletil)-2H-1,2,4-triazol-3(4H)-on (56), 4-(4-metoksifeniletil)-5-(4-nitrobenzil)-2H-1,2,4-triazol-3(4H)-on (57), 4-(4-metoksifeniletil)-5-p-tolil-2H-1,2,4-triazol-3(4H)-on (58), 5-(4-klorobenzil)-4-(4-metoksifeniletil)-2H-1,2,4-triazol-3(4H)-on(59) bileşikleri sentezlenmiştir. Sentezlenen bileşiklerden birkaçı ile (51, 52, 53, 54 ve 55) BBr3 reaksiyonundan katekol türevi olan 5 adet, 4-(4-hidroksifeniletil)-5-metil-2H-1,2,4-triazol-3(4H)-on (61), 5-etil-4-(4-hidroksifeniletil)-2H-1,2,4-triazol-3(4H)-on (62), 4-(4-hidroksifeniletil)-5-propil-2H-1,2,4-triazol-3(4H)-on (63), 4-(4-hidroksifeniletil)-5-(tiyofen-2-ilmetil)-2H-1,2,4-triazol-3(4H)-on (64), 5-benzil-4-(4-hidroksifeniletil)-2H-1,2,4-triazol-3(4H)-on (65) bileşiklerine ulaşılmıştır.Katekol türevi taşıdığı düşünülen bileşiklerin Antioksidan ve Antimikrobial aktiviteleri test edilmiş, ancak Antioksidan aktiviteleri negatif sonuçlar verirken, Antimikrobial aktivite 58 ve 64 nolu bileşiklerde gözlenmiştir.Sentezlenen orijinal nitelikte 14 adet bileşiğin yapı aydınlatılması IR , ¹H-NMR , ¹³C-NMR spektroskopi yöntemleri kullanılarak yapılmıştır ve sentezlere ilişkin reaksiyon mekanizmaları önerilmiştir.

Abstract:
In this study, novel 9 compounds 4-(4-methoxyphenylethyl)-5-2H-1,2,4-triazol-3(4H)-one (51), 5-ethyl-4-(4-methoxyphenylethyl)-2H-1,2,4-triazol-3(4H)-one (52), 4-(4-methoxyphenylethyl)-5-propyl-2H-1,2,4-triazol-3(4H)-one (53), 4-(4-methoxyphenylethyl) -5-(thiophen-2-ylmethyl)-2H-1,2,4-triazol-3(4H)-one (54), 5-benzyl-4-(4-methoxyphenylethyl)-2H-1,2,4-triazol-3(4H)-one (55), 5-(4-bromobenzyl)-4-(4-methoxyphenylethyl)-2H-1,2,4-triazol-3(4H)-one (56), 4-(4-methoxypheylethyl)-5-(4-nitrobenzyl)-2H-1,2,4-triazol-3(4H)-one (57), 4-(4-methoxyphenylethyl)-5-p-tolyl-2H-1,2,4-triazol-3(4H)-on (58), 5-(4-chlorobenzyl)-4-(4-methoxyphenylethyl)-2H-1,2,4-triazol-3(4H)-one (59) were synthesized from reaction 2-(4-methoxyphenyl)ethylamine and a series of ester ethoxy carbonyl hydrazones. Some of these compounds were treated with BBr3 to obtain novel 5 cathechol containing compounds namely, 4-(4-hydroxyphenylethyl)-5-methyl-2H-1,2,4-triazol-3(4H)-one (61), 5-ethyl-4-(4-hydroxyphenylethyl)-2H-1,2,4-triazol-3(4H)-one (62), 4-(4-hydroxyphenylethyl)-5-propyl-2H-1,2,4-triazol-3(4H)-one (63), 4-(4-hydroxyphenylethyl)-5-( thiophen -2-ylmethyl)-2H-1,2,4-triazol-3(4H)-one (64), 5-benzyl-4-(4-hydroxyphenylethyl)-2H-1,2,4-triazol-3(4H)-one (65).Compounds were though that contain catechol character were tested for their antioxidant and antimicrobial properties however all of them gave negative results for antioxidant activities. It?s determineted that antimicrobial activites 58 and 64 number compounds.The structure of 14 novel compounds synthesized in this study were analyzed by IR, 1H-NMR & 13C-NMR spectroscopy and reaction mechanisms were proposed for the general sythesis.