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Title
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Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents
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Type
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JournalPaper
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Keywords
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Chalcones Cytotoxic activity 4-Chromanone Synthesis
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Abstract
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Objective(s): Chalcones and their rigid analogues represent an important class of small molecules having anticancer activities. Therefore, in this study the synthesis and cytotoxic activity of new 3-benzylidenchroman-4-ones were described as rigid chalcone analogues. Materials and Methods: The reaction of resorcinol with 3-chloropropionic acid in the presence of CF3SO3H was afforded corresponding propiophenone. It was cyclized using 2M NaOH to give 7-hydroxy-4-chromanone. O-Alkylation of 7-hydroxy-4-chromanone with alkyl iodide in the presence of K2CO3 gave 7-alkoxychroman-4-one. Finally, condensation of chroman-4-one derivatives with different aldehydes afforded target compounds in good yields. The newly synthesized compounds were tested in vitro against different human cancer cell lines including K562 (human erythroleukemia), MDA-MB-231 (human breast cancer), and SK-N-MC (human neuroblastoma) cells. The cell viability was evaluated using MTT colorimetric assay. Results: Most of the compounds showed good inhibitory activity against cancer cells. Among them, compound 4a containing 7-hydroxy group on chromanone ring and 3-bromo-4-hydroxy-5-methoxy substitution pattern on benzylidene moiety was the most potent compound with IC50 values ≤ 3.86 μg/ml. It was 6-17 times more potent than etoposide against tested cell lines. Conclusion: We described synthesis and cytotoxic activity of poly-functionalized 3-benzylidenechroman-4-ones as new chalcone-like agents. These compounds can be considered as conformationally constrained congeners of chalcones to tolerate the poly-functionalization on the core structures for further optimization.
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Researchers
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Alireza Foroumadi (Not In First Six Researchers), Abbas Shafiee (Not In First Six Researchers), Aida Letafat (Not In First Six Researchers), Marjaneh Samadizadeh (Not In First Six Researchers), Maliheh Safavi (Not In First Six Researchers), Sussan Kaboudanian Ardestani (Not In First Six Researchers), Nayyereh Shirkavand (Not In First Six Researchers), Negar Mohammadhosseini (Fifth Researcher), Saeedeh Noushini (Fourth Researcher), Saeed Emami (Third Researcher), Bahram Letafat (First Researcher), Raheleh Shakeri (Second Researcher)
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