Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents
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 r...
| Main Authors: | , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Mashhad University of Medical Sciences
2013-11-01
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| Series: | Iranian Journal of Basic Medical Sciences |
| Subjects: | |
| Online Access: | http://ijbms.mums.ac.ir/pdf_1933_19969ded96e4c3feb2fcb849ef68c59f.html |
| _version_ | 1811261058261712896 |
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| author | Bahram letafat Raheleh Shakeri Saeed Emami Saeedeh Noushini Negar Mohammadhosseini Nayyereh Shirkavand Sussan Kabudanian Ardestani Maliheh Safavi Marjaneh Samadizadeh Aida Letafat Abbas Shafiee Alireza Foroumadi |
| author_facet | Bahram letafat Raheleh Shakeri Saeed Emami Saeedeh Noushini Negar Mohammadhosseini Nayyereh Shirkavand Sussan Kabudanian Ardestani Maliheh Safavi Marjaneh Samadizadeh Aida Letafat Abbas Shafiee Alireza Foroumadi |
| author_sort | Bahram letafat |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-12T18:56:50Z |
| format | Article |
| id | doaj.art-905d2b038f6d4703bc8020bc3083490c |
| institution | Directory Open Access Journal |
| issn | 2008-3866 2008-3874 |
| language | English |
| last_indexed | 2024-04-12T18:56:50Z |
| publishDate | 2013-11-01 |
| publisher | Mashhad University of Medical Sciences |
| record_format | Article |
| series | Iranian Journal of Basic Medical Sciences |
| spelling | doaj.art-905d2b038f6d4703bc8020bc3083490c2022-12-22T03:20:18ZengMashhad University of Medical SciencesIranian Journal of Basic Medical Sciences2008-38662008-38742013-11-011611115511621933Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like AgentsBahram letafat0Raheleh Shakeri1Saeed Emami2Saeedeh Noushini3Negar Mohammadhosseini4Nayyereh Shirkavand5Sussan Kabudanian Ardestani6Maliheh Safavi7Marjaneh Samadizadeh8Aida Letafat9Abbas Shafiee10Alireza Foroumadi11Department of Chemistry, Central Tehran-Branch, Islamic Azad University, Tehran, IranInstitute of Biochemistry and Biophysics, University of Tehran, Tehran, IranDepartment of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, IranDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, IranDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, IranDepartment of Chemistry, Central Tehran-Branch, Islamic Azad University, Tehran, IranInstitute of Biochemistry and Biophysics, University of Tehran, Tehran, IranInstitute 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, IranDepartment of Chemistry, Central Tehran-Branch, Islamic Azad University, Tehran, IranDepartment of Chemistry, Tabriz Branch, Islamic Azad University, Tabriz, IranDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, IranDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, IranObjective(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.http://ijbms.mums.ac.ir/pdf_1933_19969ded96e4c3feb2fcb849ef68c59f.htmlChalcones Cytotoxic activity 4-Chromanone Synthesis |
| spellingShingle | Bahram letafat Raheleh Shakeri Saeed Emami Saeedeh Noushini Negar Mohammadhosseini Nayyereh Shirkavand Sussan Kabudanian Ardestani Maliheh Safavi Marjaneh Samadizadeh Aida Letafat Abbas Shafiee Alireza Foroumadi Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents Iranian Journal of Basic Medical Sciences Chalcones Cytotoxic activity 4-Chromanone Synthesis |
| title | Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents |
| title_full | Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents |
| title_fullStr | Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents |
| title_full_unstemmed | Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents |
| title_short | Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents |
| title_sort | synthesis and in vitro cytotoxic activity of novel chalcone like agents |
| topic | Chalcones Cytotoxic activity 4-Chromanone Synthesis |
| url | http://ijbms.mums.ac.ir/pdf_1933_19969ded96e4c3feb2fcb849ef68c59f.html |
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