Document Detail


Synthesis and in vitro cytotoxic activity of novel chalcone-like agents.
MedLine Citation:
PMID:  24494068     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Bahram Letafat; Raheleh Shakeri; Saeed Emami; Saeedeh Noushini; Negar Mohammadhosseini; Nayyereh Shirkavand; Sussan Kabudanian Ardestani; Maliheh Safavi; Marjaneh Samadizadeh; Aida Letafat; Abbas Sha Ee; Alireza Foroumadi
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Iranian journal of basic medical sciences     Volume:  16     ISSN:  2008-3866     ISO Abbreviation:  Iran J Basic Med Sci     Publication Date:  2013 Nov 
Date Detail:
Created Date:  2014-02-04     Completed Date:  2014-02-04     Revised Date:  2014-07-31    
Medline Journal Info:
Nlm Unique ID:  101517966     Medline TA:  Iran J Basic Med Sci     Country:  Iran    
Other Details:
Languages:  eng     Pagination:  1155-62     Citation Subset:  -    
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