TAILORED FUNCTIONALIZATION OF HETEROCYCLIC DERIVATIVES OF CARBOXYLIC ACIDS AND IMINES: SYNTHESIS, CHARACTERIZATION, AND BIOLOGICAL IMPLICATIONS
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Date
2023-10-05
Authors
Inas Ibrahim Mahmoud Bsharat
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Abstract
Abstract
Background: A large number of different natural and synthetic chemicals depend on heterocyclic molecules as key building blocks due to their different structures and properties. In the presence of many drugs based on heterocyclic structures, the study of heterocyclic compounds is a prominent area in organic chemistry and has several uses in numerous industries.
Objectives: In this study, a group of ester, amide and imine compounds were prepared, and they were studied as antibacterial and anticancer, and some of them were studied as antioxidants.
Methodology: All the novel ester, amide and imine compounds in this study were prepared by condensation reactions of heterocyclic compounds, and then the new compounds were identified through FT-IR and NMR analysis, and their biological properties were tested and studied.
Results: All prepared heterocyclic compounds showed effective biological activities in varying proportions. Ee1 and E4 were the best bioactive esters in all assays. Amide A1 showed remarkable biological activity, and imines 4 and 6 were the best imines in all biological tests.
Conclusion: In this study, thymol ester E2 was better at preserving normal muscle cells than thymol. The E4 carvacrol ester compound was the best compound in its group, as it showed anti-cancer activity against HepG2 liver cancer cells in cytotoxic assay and against MCF7 breast cancer cells in cytostatic assay and also gave a distinctive activity against all types of bacteria studied. Ester compound Ea was more effective against MCF7 breast cancer cells in cytotoxic assay and against PC3 prostate cancer cells in cytostatic assay. The ester compound Eb performed better in cytotoxic and cytostatic tests on HepG2 liver cancer cells and MCF7 breast cancer cells, respectively. Ester compound Ec was more effective against Hela cancer cells and MCF7 breast cancer cells, respectively, in cytotoxic and cytostatic experiments. Also in both cytotoxic and cytostatic experiments, the ester compound Ed was more efficient against HepG2 liver cancer cells. Flavonoid ester Ee1 gave a distinctive activity in all biological tests. Amide compound A1 was the best of the compounds of its group on all the studied biological activities, as were imine 4 and imine 6 as well.
Keywords: Heterocyclic compounds; Antibacterial; Anticancer; Antioxidant.