Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents | ||
| Iranian Journal of Basic Medical Sciences | ||
| مقاله 6، دوره 16، شماره 11، بهمن 2013، صفحه 1155-1162 اصل مقاله (754.22 K) | ||
| نوع مقاله: Original Article | ||
| شناسه دیجیتال (DOI): 10.22038/ijbms.2013.1933 | ||
| نویسندگان | ||
| Bahram letafat1؛ Raheleh Shakeri2؛ Saeed Emami3؛ Saeedeh Noushini4؛ Negar Mohammadhosseini4؛ Nayyereh Shirkavand1؛ Sussan Kabudanian Ardestani2؛ Maliheh Safavi5؛ Marjaneh Samadizadeh1؛ Aida Letafat6؛ Abbas Shafiee4؛ Alireza Foroumadi* 4 | ||
| 1Department of Chemistry, Central Tehran-Branch, Islamic Azad University, Tehran, Iran | ||
| 2Institute of Biochemistry and Biophysics, University of Tehran, Tehran, Iran | ||
| 3Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran | ||
| 4Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran | ||
| 5Institute of Biochemistry and Biophysics, University of Tehran, Tehran, IranDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran | ||
| 6Department of Chemistry, Tabriz Branch, Islamic Azad University, Tabriz, Iran | ||
| چکیده | ||
| 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. | ||
| کلیدواژهها | ||
| Chalcones Cytotoxic activity 4-Chromanone Synthesis | ||
| مراجع | ||
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