Azide-Alkyne Cycloaddition En Route to 1H -1,2,3-Triazole-Tethered Isatin-Ferrocene, Ferrocenylmethoxy-Isatin, and Isatin-Ferrocenylchalcone Conjugates: Synthesis and Antiproliferative Evaluation

ACS Omega
Amandeep SinghVipan Kumar

Abstract

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.

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Citations

Feb 19, 2019·Expert Opinion on Drug Discovery·Anu RaniVipan Kumar
Apr 22, 2020·Nucleosides, Nucleotides & Nucleic Acids·Hemat S KhalafWael A El-Sayed
Feb 16, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tamer El MalahWael A El-Sayed
Mar 14, 2019·Anti-cancer Agents in Medicinal Chemistry·Kamalpreet Kaur, Vikas Jaitak
Jan 4, 2021·European Journal of Medicinal Chemistry·Sumit KumarVipan Kumar
Dec 16, 2019·European Journal of Medicinal Chemistry·Dana ElkhalifaAshraf Khalil
Jul 18, 2020·Recent Patents on Anti-cancer Drug Discovery·Katerina I SlavovaIrena P Kostova

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Methods Mentioned

BETA
column chromatography
nuclear magnetic resonance

Software Mentioned

GraphPad Prism
Excel
Magellan

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