Synthesis, Characterization and Study the Biological Activity of Some New Heterocyclic Compounds Derived from Terephthalic Acid

Journal of Chemical Health Risks

دوره 13، شماره 4، اسفند 2023، صفحه 635-645   

نوع مقاله: Original Article

شناسه دیجیتال (DOI): 10.22034/jchr.2023.1976713.1665

نویسندگان

Eman M. Hussain^* ؛ Rajaa K. Baqir؛ Jumbad H. Tomma

Department of Chemistry, College of Education for Pure Science (Ibn-Al Haitham), University of Baghdad, Baghdad, Iraq

چکیده

The organic compound imidazole has the chemical formula C₃N₂H₄. Numerous significant biological compounds contain imidazole. The amino acid histidine is the most prevalent. The substituted imidazole derivatives have great potential for treating a variety of systemic fungi infections. Thiourea is an organosulfur compound with the formula SC(NH₂)₂. It is a reagent in organic synthesis. In this paper, some new imidazole and thiourea derivatives are synthesized, characterized, and studied for their biological activity. These new compounds were synthesized from the starting material terephthalic acid, which was transformed to corresponding ester [I] by the refluxing of diacid with methanol in the presence of H₂SO₄ as a catalyst, compound [I] condensation with hydrazine hydrate 80% to yielded acid hydrazide [II], which was refluxed with 2 moles of various aromatic aldehydes in the presence of few drops of glacial acetic acid as a catalyst to yielded Schiff bases . Refluxing of chosen derivative  with acetyl chloride in dry benzene gave new acetyl compounds  which were reacted with thiourea and anhydrous sodium carbonate with acetone as a solvent to give new thiourea derivatives . Compounds  were used to synthesize new imidazole derivatives  by the reaction of appropriate compound  with 2 moles of benzoin in dry DMF under cyclization reaction. FTIR, ¹HNMR, and mass spectroscopy are used to characterize the synthesized compounds.

کلیدواژه‌ها

Acid hydrazide؛ Imidazole؛ Schiff bases؛ Terephthalic acid؛ Thiourea derivatives

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