Synthesis, structural characterization, and cytotoxic evaluation of chalcone derivatives
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Chalcones containing amino or acetamide groups on ring A and electron donating/withdrawing groups on ring B have been shown to have great cytotoxic potential against human cancer cell lines. In this work, a series of twenty chalcones, including nine 1-(4′-aminophenyl)-3-(substituted aryl)-2-propen-1-ones (1–9), nine 1-(4′-acetamidophenyl)-3-(substituted aryl)-2-propen-1-ones (1a–9a), and two 1-(3′-methoxy-4′-hydroxyphenyl)-3-(substituted aryl)-2-propen-1-ones (10, 11), were synthesized and submitted for initial biological screening using HCT-116 cells. Among the evaluated compounds, chalcone 6a showed strong and selective activity against HCT-116 cells (IC50 = 2.37 ± 0.73 µM). The preliminary structure–activity relationship analysis indicated that the cytotoxic effect of these compounds might be attributed to the combined effect of two electron withdrawing groups: the nitro group (NO2) at the meta-position of ring B and the acetyl group at the para-position of ring A. Moreover, chalcone 6a was able to induce G2/M cell cycle arrest and apoptosis at a concentration of 10 µM after 24 h of incubation. These data reinforce that compound 6a could be a promising lead compound for the future exploration of selective anti-colon carcinoma cancer agents.
KeywordsSynthesis NMR Infrared Chalcone 4′-acetamidochalcones Cytotoxic activity
The authors thank the National Cancer Institute (Bethesda, MD, USA) for donating of all human tumor cell lines used in this study. CENAUREMN—Northeastern Center for the Application and Use of Nuclear Magnetic Resonance and EMBRAPA AGROINDÚSTRIA TROPICAL-Multiuser Laboratory of Natural Product Chemistry by obtaining the spectral data. Teixeira AMR also acknowledges financial support from the PQ/CNPq (Grant#: 3 05719/2018-1).
Compliance with ethical standards
Conflict of interest
The authors declare that they have no conflict of interest.
This article does not contain any studies with human participants or animals performed by any of the authors.
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