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Synthesis and Anti‐Cancer Activity Evaluation of New Dimethoxylated Chalcone and Flavanone Analogs
Author(s) -
Ketabforoosh Shima H. M. E.,
Kheirollahi Asma,
Safavi Maliheh,
Esmati Nasim,
Ardestani Sussan K.,
Emami Saeed,
Firoozpour Loghman,
Shafiee Abbas,
Foroumadi Alireza
Publication year - 2014
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201400215
Subject(s) - chalcone , flavanone , chemistry , cytotoxicity , stereochemistry , apoptosis , moiety , cancer cell , cancer , cell culture , etoposide , biochemistry , pharmacology , flavonoid , in vitro , antioxidant , biology , chemotherapy , genetics
A novel series of chalcones and flavanones discriminated by the presence of a 3,4‐dimethoxyphenyl moiety in their structures were synthesized as anti‐cancer agents. The cytotoxicity evaluation of the analogs against the MCF‐7, MDA‐MB‐231 (human breast cancer), and SK‐N‐MC (human neuroblastoma) cell lines demonstrated that the introduction of a halogen on the 3,4‐dimethoxyphenyl part of both series and the attachment of a pyrrolidinylethoxy group on the C‐7 position of the flavanone derivatives increased their activity. Indeed, 3‐halogenated chalcones ( 1c and 1d ) were more potent than the standard drug etoposide against all tested cell lines. Fluorescence microscopy and flow cytometry analyses confirmed that the anti‐cancer effect of the most potent compounds 1c and 1d occurs via apoptosis induction.