SELECTIVE SYNTHESIS OF THE NOVEL S-ALKYL 3-PHENYLQUINAZOLIN-4(3H)-ONES
Abstract
In recent years, quinazolones have been extensively investigated as inhibitors of biological targets involved in numerous biochemical processes. Therefore, considerable research efforts have been directed toward the targeted synthesis and structural modification of these heterocyclic compounds, evaluation of their biological activities, and the development of novel drug candidates based on promising biologically active molecules. Drugs such as neratinib, fruquintinib, and vandetanib, which have recently been used in the treatment of tuberculosis and cancer, are representative examples of the therapeutic potential of quinazolone-based compounds [1,2]. In this study, the 2-mercapto-3-phenylquinazolin-4(3H)-one (1) was subjected to S-alkylation with various alkylating agents in DMF in the presence of K2CO3 at 75–80°C for 4 h. As the alkylating agents were used methyl iodide, 2-methoxyethyl chloride and heptyl bromide. As a result, the corresponding S-methyl- (2), S-(2-methoxyethyl)- (3), and S-heptyl- (4) derivatives were obtained. The target products were synthesized in good (67-70%) yields. The physicochemical properties of the synthesized compounds were characterized by 1H NMR and single crystal X-ray structure analysis. The use of different alkylating reagents enabled the synthesis of new alkyl thioether derivatives.
References
- Kalpana Singh, P.P. Sharma, A. Kumar, Anurag Chaudhary, R.K. Roy. (2013). 4-Aminoquinazoline Analogs: A Novel Class of Anticancer Agents.Mini-Reviews in Medicinal Chemistry.[Crossref]
- Prashant S. Auti, Ginson George, Atish T. Paul. (2020). Recent advances in the pharmacological diversification of quinazoline/quinazolinone hybrids.RSC Advances.[Crossref]
Publication Details
This article is licensed under a Creative Commons Attribution 4.0 International License.