Synthesis and Antioxidant Characteristics of Novel Heterocyclic Derivatives from 2-Thiol-5-Phenyl-1,3,4-Oxadiazole Compounds

Sumaya J. Jamal; Mohammed R.  Ahmad

doi:10.30526/37.4.3340

Authors

Sumaya J. Abed Department of Chemistry, College of Science, University of Baghdad and College of Dentistry/ Al-Iraqia University, Baghdad, Iraq. https://orcid.org/0009-0007-0287-0682
Mohammed R. Ahmad Department of Chemistry, College of Science, University of Baghdad, Baghdad, Iraq. https://orcid.org/0000-0002-2643-0813

DOI:

https://doi.org/10.30526/37.4.3340

Keywords:

Antioxidant activities, heterocyclic, oxadiazole, Schiff bases

Abstract

The 1,3,4-Oxadiazole-bearing compounds are among the most attractive classes for researchers because of their biological processes. The study used a current show of quinazoline-4-one and oxazine-4-one derivatives (8-13) were synthesized. Firstly; the reaction of benzyl salicylate was reacted with hydrazine hydrate (99%) to give 2-hydroxybenzohydrazide (1) then the produced was reacted with carbon disulfide dissolved in absolute ethanol and potassium hydroxide to make 2-(5-mercapto-1,3,4-oxadiazol-2-yl)phenol (2). After that, compound (2) was treated with ethyl chloroacetate to give ethyl 2-((5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)thio)acetate (3). Hydrazine hydrate and compound (3) interacted to create 2-((5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)thio) acetohydrazide (4) next combined with a different aromatic aldehyde substitution in absolute ethanol to produce derivatives of Schiff's bases (5-7). Lastly, preparations were made for the target compounds (8–13) by interacting chemicals (5-7) with anthranilic and salicylic acid. Using [FT-IR, 1H-NMR, and 13C-NMR] and measuring their physical properties, the newly synthesized compounds were recognized. We also examined the potential anti-oxidant properties of produced compounds. According to the obtained data, the synthesized compounds showed different inhibition activities against free radicals. Moreover, compounds (10 and 13) were found to be most effective against DPPH radicals, and higher than that of BHT. It has been concluded that the synthesized compounds have therapeutic potential for diseases mediated by oxidative stress.

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