%0 Journal Article %T Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents %J Iranian Journal of Basic Medical Sciences %I Mashhad University of Medical Sciences %Z 2008-3866 %A letafat, Bahram %A Shakeri, Raheleh %A Emami, Saeed %A Noushini, Saeedeh %A Mohammadhosseini, Negar %A Shirkavand, Nayyereh %A Kabudanian Ardestani, Sussan %A Safavi, Maliheh %A Samadizadeh, Marjaneh %A Letafat, Aida %A Shafiee, Abbas %A Foroumadi, Alireza %D 2013 %\ 11/01/2013 %V 16 %N 11 %P 1155-1162 %! Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents %K Chalcones Cytotoxic activity 4-Chromanone Synthesis %R 10.22038/ijbms.2013.1933 %X   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. %U https://ijbms.mums.ac.ir/article_1933_19969ded96e4c3feb2fcb849ef68c59f.pdf