Azide–Alkyne Cycloaddition En Route to 1H-123-Triazole-Tethered Isatin–FerroceneFerrocenylmethoxy–Isatin and Isatin–FerrocenylchalconeConjugates: Synthesis and Antiproliferative Evaluation

摘要

Diverse series of isatin–ferrocene conjugates were synthesized via Cu-promoted azide–alkyne cycloaddition reaction with an aim of probing their antiproliferative structure–activity relationship against MCF-7 (estrogen receptor positive) and MDA-MB-231 (triple negative) cell lines. Among the synthesized conjugates, isatin–ferrocenes proved to be more potent against MCF-7, whereas ferrocenylmethoxy–isatins exhibited activity against MDA-MB-231 cell lines. However, the introduction of chalcone moiety among these hybrids resulted in the complete loss of activity against the tested cell lines, as evident by isatin–ferrocenylchalcones. The conjugates >5a and >9c proved to be the most potent among the series against MCF-7 and MDA-MB-213 cell lines, exhibiting IC50 values of 31.62 and 20.26 μM, respectively.