Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents

letafat, Bahram and Shakeri, Raheleh and Emami, Saeed and Noushini, Saeedeh and Mohammadhosseini, Negar and Shirkavand, Nayyereh and Kabudanian Ardestani, Sussan and Safavi, Maliheh and Samadizadeh, Marjaneh and Letafat, Aida and Shafiee, Abbas and Foroumadi, Alireza (2013) Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents. Iranian Journal of Basic Medical Sciences, 16 (11). pp. 1155-1162.

[img]
Preview
Text
IJBMS_Volume 16_Issue 11_Pages 1155-1162.pdf

Download (772kB) | Preview
Official URL: http://ijbms.mums.ac.ir/article_1933.html

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 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.

Item Type: Article
Subjects: QV pharmacology
Divisions: Journals > Iranian J Basic Medical Sciences
Depositing User: ijbms ijbms
Date Deposited: 09 Oct 2017 17:15
Last Modified: 09 Oct 2017 17:15
URI: http://eprints.mums.ac.ir/id/eprint/8075

Actions (login required)

View Item View Item