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Synthesis, Structure, Electrochemistry, and In Vitro Anticancer and Anti-Migratory Activities of (Z)- and (E)-2-Substituted-3-Ferrocene-Acrylonitrile Hybrids and Their Derivatives
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Synthesis, Structure, Electrochemistry, and In Vitro Anticancer and Anti-Migratory Activities of (Z)- and (E)-2-Substituted-3-Ferrocene-Acrylonitrile Hybrids and Their Derivatives
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Synthesis, Structure, Electrochemistry, and In Vitro Anticancer and Anti-Migratory Activities of (Z)- and (E)-2-Substituted-3-Ferrocene-Acrylonitrile Hybrids and Their Derivatives
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Journal Article
Synthesis, Structure, Electrochemistry, and In Vitro Anticancer and Anti-Migratory Activities of (Z)- and (E)-2-Substituted-3-Ferrocene-Acrylonitrile Hybrids and Their Derivatives
2025
Overview
In this study, a series of (Z)- and (E)-2-substituted-3-ferrocene-acrylonitrile derivatives were synthesized, characterized, and evaluated in vitro for their anticancer and anti-migration properties. The compounds were synthesized via the Knoevenagel condensation of the appropriate benzyl cyanide or benzoyl acetonitrile with ferrocenecarboxaldehyde 1, producing isolated yields of 99 to 23%. The structures of the compounds were analyzed using IR, 1H NMR, 13C1H NMR, GC-MS, and UV/Vis spectroscopic methods. Single-crystal X-ray diffraction analysis of representative compounds 21, 27, and 29 demonstrated that the geometry of the double bond was that of the (Z)-isomer. For representative compound 33, the geometry of the double bond was that of the (E)-isomer. Additionally, the electrochemistry of the compounds was investigated using cyclic voltammetry. The cytotoxic and anti-migratory effects of these compounds were evaluated in the MCF-7 and MDA-MB-231 breast cancer cell lines, providing insight into the structure–activity relationships. Preliminary investigations of their anticancer activity revealed that several compounds exhibit moderate antiproliferative effects on cancer cell lines, with GI50 values ranging from 23 to 44 μM for the MCF-7 cell line and from 9 to 41 μM for the MDA-MB-231 cell line. Moreover, compound (Z)-25 inhibited 13% of the migration activity of the metastatic MDA-MB-231 cell line.
Publisher
MDPI AG,MDPI
Subject
/ Acrylonitrile - chemical synthesis
/ Acrylonitrile - pharmacology
/ Analysis
/ Antineoplastic Agents - chemical synthesis
/ Antineoplastic Agents - chemistry
/ Antineoplastic Agents - pharmacology
/ Cancer
/ Cell Movement - drug effects
/ Cell Proliferation - drug effects
/ Ferrous Compounds - chemical synthesis
/ Ferrous Compounds - chemistry
/ Ferrous Compounds - pharmacology
/ Geometry
/ Humans
/ Ligands
/ Metallocenes - chemical synthesis
/ Structure-Activity Relationship
/ Tumors
/ X-rays
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