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- Title
Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents.
- Authors
Letafat, Bahram; Shakeri, Raheleh; Emami, Saeed; Noushini, Saeedeh; Mohammadhosseini, Negar; Shirkavand, Nayyereh; Ardestani, Sussan Kabudanian; Safavi, Maliheh; Samadizadeh, Marjaneh; Letafat, Aida; Shafiee, Abbas; Foroumadi, Alireza
- Abstract
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 CF3SO 3H 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.
- Subjects
CHALCONES; CELL survival; CELL lines; CELLULAR pathology; MOLECULAR biology
- Publication
Iranian Journal of Basic Medical Sciences, 2013, Vol 16, Issue 11, p1155
- ISSN
2008-3866
- Publication type
Article