Synthesis and in vitro Antioxidant Activities of Novel 2-Methoxy-6-[(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl)-azomethine]phenyl Furan-2-carboxylate Derivatives

Abstract

Heterocyclic compounds bearing 1,2,4-triazole and 4,5-dihydro-1H-1,2,4-triazole-5-one ring show a wide spectrum of biological activity. Schiff bases have various practical applications such as dyes, textile, cosmetics, analytical reagents, water treatment products, petroleum additives, synthetic polymer products, the improvement of natural macromolecular materials like leather and paper. However, the most important application area of Schiff Bases is pharmaceutical chemistry. It is hoped that Schiff bases containing a potentially biologically active 1,2,4-triazole ring will provide useful molecules that can be used in the treatment of many diseases and drugs that can be used in the treatment of future diseases. In this regard, new 2-methoxy-6-[(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl)-azomethine]phenyl furan-2-carboxylates (3) were obtained from the reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1) with 2-formyl-6-methoxyphenyl furan-2-carboxylate (2). Then, acetylation reactions of 3 compounds were examined and 2-methoxy-6-[(1-acetyl-3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl)-azomethine]phenyl furan-2-carboxylates (4) were synthesized. The structures of fourteen new compounds were characterized by IR, 1H NMR, 13C NMR and UV spectral data. Besides, in vitro antioxidant properties of the newly synthesized 3 and 4 type compounds were evaluated by three different methods (reduction power, free radical removal activity and metal chelate activity).

Keywords

• Schiff base
• 4
• 5-Dihydro-1H-1
• 2
• 4-triazol-5-one
• Syntheses
• Acetylation
• Antioxidant Activity

Yeni 2-Metoksi-6-[(3-alkil/aril-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il)-azometin]fenil Furan-2-karboksilat Türevlerinin Sentezi ve in vitro Antioksidan Aktiviteleri

Öz

1,2,4-Triazol ve 4,5-dihidro-1H-1,2,4-triazol-5-on halkası taşıyan heterosiklik bileşikler çok geniş bir spektrumda biyolojik aktivite göstermektedir. Schiff bazlarının ise boya, tekstil, kozmetik, analitik reaktifler, su iyileştirme ürünleri, petrol katkı maddeleri, sentetik polimer ürünleri, deri ve kağıt gibi doğal makromoleküler materyallerin iyileştirilmesi gibi çeşitli pratik uygulamaları bulunmaktadır. Ancak Schiff Bazlarının en önemli uygulama alanı ilaç kimyasıdır. Potansiyel biyolojik aktif 1,2,4-triazol halkası içeren Schiff bazlarının birçok hastalığın tedavisinde kullanılabilecek faydalı moleküllerin ve ileride hastalıkların tedavisinde kullanılabilecek ilaçların elde edilmesi ümit edilmektedir. Bu amaçla 3-alkil(aril)-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on’ların (1), 2-formil-6-metoksifenil furan-2-karboksilat (2) ile reaksiyonundan 2-metoksi-6-[(3-alkil/aril-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il)-azometin]fenil furan-2-karboksilatlar (3) elde edilmiştir. Daha sonra 3 bileşiklerinin asetilasyon reaksiyonları incelenerek 2-metoksi-6-[(1-asetil-3-alkil/aril-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il)-azometin]fenil furan-2-karboksilatlar (4) sentezlenmiştir. On dört yeni bileşiğin yapıları IR, 1H NMR, 13C NMR ve UV spektral verileri kullanılarak aydınlatılmıştır. Ayrıca, sentezlenen 3 ve 4 tipi yeni bileşiklerin üç farklı yöntemle (indirgeme gücü, serbest radikal giderme aktivitesi ve metal şelat aktivitesi) in vitro antioksidan özellikleri değerlendirilmiştir.

Anahtar Kelimeler

• Schiff bazı
• Sentez
• Asetilasyon
• Antioksidan Aktivitesi

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