Synthesis, characterization, and biological evaluation of new heterocyclic systems 1, 2, 3-triazole-isoxazoline from eugenol by the mixed condensation reactions

Application of triazoles in the structural modification of natural products

“…Taia et al. 105 reported the synthesis of a new series of heterocyclic eugenol derivatives through the mixed condensation reaction of 1,3-dipolar azide and the oxide of p-chlorophenylnitrile on 4-allyl-2-methoxy-1-(prop-2-yn-1-yloxy) benzene. The monoadducts and bis-heterocyclic derivatives were active against the fibrosarcoma cell line and against lung and breast carcinoma cell lines.…”

“…Eugenol-triazole derivatives not only possess anti-cancer activity 105 , but also they exhibit anti-leishmanial activity 135 . Eugenol derivatives exert leishmanicidal activities with varying degrees of effectiveness 135 .…”

“…Eugenol-triazole derivatives not only possess anticancer activity 105 and anti-leishmanial activity 135 , but also they exhibit anti-Trypanosoma cruzi activity 148 . De Souza et al.…”

Tailored Functionalization of Natural Phenols to Improve Biological Activity

“…Numerous eugenol derivatives bearing triazole functionalities have been successfully accessed through the “click chemistry” approach ( Figure 4 , Scheme 18 ). Several examples are present in the literature about ( i ) O -alkylation of eugenol with terminal alkynes, followed by reaction with different benzyl azides [ 203 , 204 , 205 ]; ( ii ) eugenol conversion in epoxide and ring opening to obtain the corresponding alkyl azides, followed by reaction with different alkynes [ 206 ]; ( iii ) hydroboration oxidation at the allylic position of eugenol, followed by mesylation and azidation reactions, to achieve the eugenol azide; then, reaction with phenylacetylene to afford the triazole. Importantly, the first step of this latter process requires -OH protection trough silylation, thus allowing the synthesis of variously substituted products ( Scheme 18 ) [ 207 ].…”

“…Synthesized eugenol triazole derivatives showed leishmanicidal [ 205 ], antimycobacterial [ 207 ], trypanocidal [ 206 ], anticancer [ 203 ] as well as protease inhibitory [ 204 ] activity. Triazole eugenol glucosides also showed significant bactericidal activity and low toxicity to normal cells [ 208 ].…”