Synthesis, Antioxidant and Antibacterial Activities of Salicylaldehyde Azine

Abstract

Salicylaldehyde azine (SA) were synthesized with salicylaldehyde and hydrazine hydrate as a raw material. The crystal structure was characterized by X-ray diffraction, as well as the total antioxidant capacity and antibacterial activities against Staphylococcus aureus and Escherichia coli were investigated. It was found that SA exhibited significant antibacterial activities and total antioxidant capacity.

The Reaction of Ethyl 2-oxo-2H-chromene-3-carboxylate with Hydrazine Hydrate

“…In an exhaustive literature survey of the reaction product(s) of ester 1 and hydrazine hydrate, bearing in consideration the possible ring-openings of chromene-2-ones [ 37 ], Soliman et al [ 38 ] described, in 1985, the reaction of ethyl 2-oxo-2 H -chromene-3-carboxylate ( 1 ) with hydrazine hydrate in refluxing ethanol, in which they obtained salicylaldehyde azine ( 3 ) in 31.5% and 42.4% yields for one and two equivalent of hydrazine hydrate, respectively, instead of the claimed hydrazide 2 . The structure of the well-known and commercially available salicylaldehyde azine ( 3 ), was rigorously proven by independent synthesis using the reaction of salicylaldehyde with hydrazine hydrate [ 39 ]. Comparison of the melting point and spectral data for an authentic sample of compound 3 and the yellow crystals produced in our trials, gave us absolute confidence to assign the structure of these crystals to be salicylaldehyde azine ( 3 ), in complete agreement with the results of Soliman and his co-workers ( Scheme 1 ).…”

“…A mixture of ethyl 2-oxo-2 H -chromene-3-carboxylate ( 1 , 2.18 g, 10 mmol) and hydrazine hydrate, (99%, 1.3 g, 25 mmol) in absolute ethanol (50 mL) was heated under reflux for 2 h. The precipitate formed was filtered off, washed with ethanol and dried. Recrystallization from ethanol gave yellow crystalsof salicyaldehyde azine ( 3 ) [ 38 , 39 ] (1.15 g, 48%); m.p. 205–206 °C (204.3 °C) [ 39 ]; IR ν 3350–2830 (OH), 1633 (C=N) cm −1 ; 1 H-NMR δ 6.84–7.72 (m, 8H, ArH), 8.86 (s, 2H, –CH=), 10.90 (s, D 2 O exch., 2H, OH); 13 C-NMR δ 117.9, 118.7, 121.4, 132.0, 132.5, 159.2, 162.0; MS m/z : 240.5 (M + ).…”

“…Recrystallization from ethanol gave yellow crystalsof salicyaldehyde azine ( 3 ) [ 38 , 39 ] (1.15 g, 48%); m.p. 205–206 °C (204.3 °C) [ 39 ]; IR ν 3350–2830 (OH), 1633 (C=N) cm −1 ; 1 H-NMR δ 6.84–7.72 (m, 8H, ArH), 8.86 (s, 2H, –CH=), 10.90 (s, D 2 O exch., 2H, OH); 13 C-NMR δ 117.9, 118.7, 121.4, 132.0, 132.5, 159.2, 162.0; MS m/z : 240.5 (M + ). Anal.…”

Fluorescence staining of salicylaldehyde azine, and applications in the determination of potassium tert-butoxide

“…17 Some uorescent compounds have been successfully synthesized to overcome this disadvantage such as polythiophene and its derivatives, 18,19 as well as tetraphenylethene derivatives, 20 1methyl-1,2,3,4,5-pentaphenylsilole, 21 and p-sexiphenyl. 22 Concurrently, some studies on salicylaldehyde azines have been reported including pharmacological proprieties 23,24 and optical properties. 25,26 The AIE characteristic of salicylaldehyde azine was rst fully studied by Tang.…”

Synthesis, complete assignment of 1H- and 13C-NMR spectra and antioxidant activity of new azine derivative bearing coumarin moiety

“…The chemical properties and biological activities of these compounds mostly are the consequence of the presence of double bonds and nitrogen atoms. It is well known that they possess antibacterial (Veena et al, 2011;Chourasiya et al, 2015), antifungal (Kurteva et al, 2011), anticonvulsant (Gul et al, 2004), antineuroinflammatory (Subedi et al, 2017), anticancer (Krezel et al, 1999;Qian et al, 2010;Liang et al, 2014) and antioxidant (Li et al, 2011) activities. Also, they behave as aldose reductase inhibitors (Meanwell et al, 1991) and MDR reversal agents (Paterna et al, 2018).…”