SYNTHESIS AND IN VITRO CYTOTOXIC ACTIVITY OF NOVEL CHALCONE-LIKE AGENTS

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LETAFAT BAHRAM; SHAKERI RAHELEH; EMAMI SAEED; NOUSHINI SAEEDEH; MOHAMMADHOSSEINI NEGAR; SHIRKAVAND NAYYEREH; KABUDANIAN ARDESTANI SUSSAN; SAFAVI MALIHEH; SAMADIZADEH MARJANEH; LETAFAT AIDA; SHAFIEE ABBAS; FOROUMADI ALIREZA

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Journal: Iranian Journal of Basic Medical Sciences Year:2013 | Volume:16 | Issue:11 Page(s): 1155-1162

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Title

SYNTHESIS AND IN VITRO CYTOTOXIC ACTIVITY OF NOVEL CHALCONE-LIKE AGENTS

Author(s)

Keywords

CHALCONES

CYTOTOXIC ACTIVITY

4-CHROMANONE

SYNTHESIS

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 mg/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.

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APA: Copy

LETAFAT, BAHRAM, SHAKERI, RAHELEH, EMAMI, SAEED, NOUSHINI, SAEEDEH, MOHAMMADHOSSEINI, NEGAR, SHIRKAVAND, NAYYEREH, KABUDANIAN ARDESTANI, SUSSAN, SAFAVI, MALIHEH, SAMADIZADEH, MARJANEH, LETAFAT, AIDA, SHAFIEE, ABBAS, & FOROUMADI, ALIREZA. (2013). SYNTHESIS AND IN VITRO CYTOTOXIC ACTIVITY OF NOVEL CHALCONE-LIKE AGENTS. IRANIAN JOURNAL OF BASIC MEDICAL SCIENCES, 16(11), 1155-1162. SID. https://sid.ir/paper/630557/en

Vancouver: Copy

LETAFAT BAHRAM, SHAKERI RAHELEH, EMAMI SAEED, NOUSHINI SAEEDEH, MOHAMMADHOSSEINI NEGAR, SHIRKAVAND NAYYEREH, KABUDANIAN ARDESTANI SUSSAN, SAFAVI MALIHEH, SAMADIZADEH MARJANEH, LETAFAT AIDA, SHAFIEE ABBAS, FOROUMADI ALIREZA. SYNTHESIS AND IN VITRO CYTOTOXIC ACTIVITY OF NOVEL CHALCONE-LIKE AGENTS. IRANIAN JOURNAL OF BASIC MEDICAL SCIENCES[Internet]. 2013;16(11):1155-1162. Available from: https://sid.ir/paper/630557/en

IEEE: Copy

BAHRAM LETAFAT, RAHELEH SHAKERI, SAEED EMAMI, SAEEDEH NOUSHINI, NEGAR MOHAMMADHOSSEINI, NAYYEREH SHIRKAVAND, SUSSAN KABUDANIAN ARDESTANI, MALIHEH SAFAVI, MARJANEH SAMADIZADEH, AIDA LETAFAT, ABBAS SHAFIEE, and ALIREZA FOROUMADI, “SYNTHESIS AND IN VITRO CYTOTOXIC ACTIVITY OF NOVEL CHALCONE-LIKE AGENTS,” IRANIAN JOURNAL OF BASIC MEDICAL SCIENCES, vol. 16, no. 11, pp. 1155–1162, 2013, [Online]. Available: https://sid.ir/paper/630557/en

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