Synthesis of 5-Amino-4-Carboxylate-1,2,3-triazole-Chalcone Structures

The 12th International Drug Chemistry Congress, Antalya, Türkiye, 7 - 10 Mart 2024, ss.159

Thanks to their strong antioxidant properties, chalcones can protect the body from the harmful effects of free

radicals, reduce inflammation, support the immune system.1

Some studies have shown that chalcones can be

used as potential treatment agents for various types of cancers, such as breast cancer, colon cancer, lung

cancer and prostate cancer.2,3 Chalcones attract the attention of researchers due to the wide range of

biological effetcs they exhibit,and today intensive studies are being conducted on the synthesis and biological

effects of new chalcone structures with some changes in the structures of natural chalcones. 1,2,3-Triazoles are

an important class of nitrogen-containing heterocyclic compounds with broad applications in synthetics and

attract attention due to their wide range of biological properties such as antifungal, anti-HIV, antimalarial and

anti-inflammatory.4

1,2,3-Triazoles have a high dipole moment and their active participation in hydrogen bond

formation, dipole-dipole and π stacking interactions helps them to easily bind to biological targets and increase

their solubility.5,6 In this study, we synthesized 12 new chalcone-5-amino-1,2,3-triazole hybrid molecules. For

this purpose, we first synthesized 4-acetylphenzylazide from 4-acetylaniline. The reaction of 4-

acetylphenzylazide with ethyl cyanoacetate gave ethyl 1-(4-acetylphenyl)-5-amino-1H-1,2,3-triazole-4-

carboxylate. Finally the Claisen-Schmidt condensation of them with benzaldehydes produce diethyl 5-amino-1-

(4-cinnamoylphenyl)-1H-1,2,3-triazole-4-carboxylate. The structures of all the new compounds were

characterized using IR, 1

H and 13CNMR spectroscopic methods.