Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents
Letafat, B; Shakeri, R; Emami, S; Noushini, S; Mohammadhosseini, N; Shirkavand, N; Ardestani, SK; Safavi, M; Samadizadeh, M; Letafat, A; Shafiee, A; Foroumadi, A
HERO ID
5410581
Reference Type
Journal Article
Year
2013
Language
English
PMID
| HERO ID | 5410581 |
|---|---|
| In Press | No |
| Year | 2013 |
| Title | Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents |
| Authors | Letafat, B; Shakeri, R; Emami, S; Noushini, S; Mohammadhosseini, N; Shirkavand, N; Ardestani, SK; Safavi, M; Samadizadeh, M; Letafat, A; Shafiee, A; Foroumadi, A |
| Journal | Iranian Journal of Basic Medical Sciences |
| Volume | 16 |
| Issue | 11 |
| Page Numbers | 1155-1162 |
| Abstract | <strong>OBJECTIVE(S): </strong>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.<br /><br /><strong>MATERIALS AND METHODS: </strong>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.<br /><br /><strong>RESULTS: </strong>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.<br /><br /><strong>CONCLUSION: </strong>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. |
| Pmid | 24494068 |
| Wosid | WOS:000330338300006 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |
| Keyword | Chalcones; Cytotoxic activity; 4-Chromanone; Synthesis |