Bazı yeni 3-alkil(aril)-4-(3-metoksi-4-sinnamoiloksi)benzilidenamino-4,5- dihidro-1H-1,2,4-triazol-5-on bileşiklerinin sentezi, antioksidan ve asitlik özelliklerinin incelenmesi

Öz

3-Alkil(aril)-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on (2) bileşiklerinin, 3-metoksi-4-sinnamoiloksibenzaldehid (3) ile reaksiyonları sonucunda dokuz yeni 3-alkil(aril)-4-(3-metoksi-4-sinnamoiloksi)-benzilidenamino-4,5-dihidro-1H-1,2,4-triazol5-on (4) bileşikleri sentezlendi. Yeni dokuz adet bileşiğin yapısı IR, 1H-NMR, 13C-NMR ve UV spektrum verileri ile aydınlatıldı. Sentezlenen bileşiklerin in vitro antioksidan aktiviteleri üç farklı yöntemle analiz edildi. Ayrıca, çözücülerin ve moleküler yapının asitlik üzerine etkisini incelemek için, 4 bileşikleri dört farklı çözücüde (izopropil alkol, tert-butil alkol, aseton ve N,Ndimetilformamid) tetrabutilamonyum hidroksid ile potansiyometrik metotla titre edildi. HNP ve pKa değerlerinin çözücüye ve
4,5-dihidro-1H-1,2,4-triazol-5-on yapısında C-3 pozisyonundaki substutiente bağlı değiştiği gözlendi.

Anahtar Kelimeler

• 1
• 2
• 4-Triazol-5-on
• sentez
• Schiff bazı
• antioksidan aktivite
• asitlik

Synthesis, antioxidant and acidic properties of some new 3-alkyl(aryl)-4-(3- methoxy-4-cinnamoyloxy)benzylideneamino-4,5-dihydro-1H-1,2,4-triazol5-ones

Abstract

Nine new 3-alkyl(aryl)-4-(3-methoxy-4-cinnamoyloxy)benzylideneamino-4,5-dihydro-1H-1,2,4-triazol-5-ones (4) were synthesized by the reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2) with 3-methoxy-4-cinnamoyloxybenzaldehyde (3). The structures of new nine compounds were established from IR, ¹H-NMR, ¹³C-NMR and UV spectral data. The synthesized compounds were analyzed for their in vitro potential antioxidant activities in three different methods. In addition, to investigate the effects of solvents and molecular structure upon acidity compounds 4 were titrated potentiometrically with tetrabutylammonium hydroxide in four non-aqueous solvents (isopropyl alcohol, tert-butyl alcohol, acetone and N,N-dimethylformamide).

Keywords

• 1.2.4-Triazol-5-one
• Schiff base
• synthesis
• antioxidant activity
• acidity

References

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