scholarly journals SYNTHESIS, COMPLETE ASSIGNMENT OF 1H- AND 13C-NMR SPECTRA AND ANTIOXIDANT ACTIVITY OF NEW AZINE DERIVATIVE BEARING COUMARIN MOIETY

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Milenko Ristić ◽  
Biljana Dekić ◽  
Niko Radulović ◽  
Marija Aksić

In this research, the synthesis of a new azine derivative with coumarin moiety was performed in three reaction steps, starting from 4-hydroxycoumarin. The first step in synthesis was the acetylation of 4-hydroxycoumarin to yield 3-acetyl-4-hydroxycoumarin and then the obtained 3-acetyl-4-hydroxycoumarin was reacted with hydrazine hydrate and give a corresponding hydrazone. Condensation of the hydrazone with 4-ethoxy-3-methoxybenzaldehyde afforded the target compound 1-[1-(4-hydroxy-2-oxo-2H-chromen-3-yl)-ethylidene]-2-(4-etoxy-3-methoxybenzylidene)-hydrazine in a good yield. The resulting azine derivative is fully spectrally characterized, including complete assignment of 1H- and 13C-NMR spectra, as well as 2D NMR (1H-1H COSY, NOESY, HSQC and HMBC) spectra. The antioxidant activity of corresponding hydrazone and target compound was evaluated by DPPH method where hydrazone derivative displayed a significant and target azine good antioxidant activity, with IC50 (μM) values 11.69 and 216.60, respectively.

2015 ◽  
Vol 13 (2) ◽  
pp. 121-132 ◽  
Author(s):  
Ana Miltojevic ◽  
Niko Radulovic

We report on the detailed NMR spectral analyses of amino- or/and hydroxy-substituted benzoic acids: anthranilic (AA), 3-hydroxyanthranilic (3-HAA), 5-hydroxyanthranilic (5-HAA), salicylic (SA), 4-aminosalicylic (4-ASA) and 5-aminosalicylic (5-ASA) acids. According to a literature survey, there are limited, unassigned or even incorrectly assigned spectral data to these benzoic acid derivatives. In order to amend the situation, a complete assignment of 1H- and 13C-NMR spectra of these compounds, recorded in perdeuteriodimethyl sulfoxide (DMSO-d6), based on a combination of 1D- and 2D-NMR experiments, including 1H-1H COSY, NOESY, HSQC and HMBC, was performed.


2011 ◽  
Vol 49 (7) ◽  
pp. 437-442 ◽  
Author(s):  
Pedro Besada ◽  
Tamara Costas ◽  
Noemi Vila ◽  
Carla Chessa ◽  
Carmen Terán

2010 ◽  
Vol 48 (11) ◽  
pp. 896-902 ◽  
Author(s):  
Vidoslav Dekić ◽  
Niko Radulović ◽  
Rastko Vukićević ◽  
Biljana Dekić ◽  
Danielle Skropeta ◽  
...  

Tetrahedron ◽  
1995 ◽  
Vol 51 (26) ◽  
pp. 7215-7222 ◽  
Author(s):  
John A. Parkinson ◽  
Ian H. Sadler ◽  
Michael B. Pickup ◽  
Alethea B. Tabor

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