Synthesis and Anticancer Activity of Triazole Linked Macrocycles and Heterocycles

Synthesis of macrocylic enones starting from alkyl ether and triazole as a linker was achieved using click reaction and intramolecular aldol condensation. The newly synthesized macrocyclic enone was successfully utilized as a dipolarophile in 1,3-dipolar cycloaddition. The dipoles generated from hydrazine hydrochloride, hydroxylamine and guanidine hydrochloride were reacted with macrocyclic enone to give a new class of spiro aminopyrimidines, phenyl pyrazoles and isoxazoles grafted macrocycles in good yield. The structures of newly synthesized compounds were confirmed with IR, NMR and mass spectroscopy and evaluated for their anti cancer activity.

Automated summary

In this study, macrocyclic enones were successfully synthesized starting from alkyl ether and triazole as a linker using click reaction and intramolecular aldol condensation. The newly synthesized macrocyclic enone demonstrated good reactivity as a dipolarophile in 1,3-dipolar cycloaddition and reacted with dipoles generated from hydrazine hydrochloride, hydroxylamine, and guanidine hydrochloride to form a new class of spiro aminopyrimidines, phenyl pyrazoles, and isoxazoles grafted macrocycles in good yield. The structures of the newly synthesized compounds were confirmed using IR, NMR, and mass spectroscopy and evaluated for their anti-cancer activity.