Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 35, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2021.127827
Keywords
Synthesis; Claisen-Schmidt condensation; Nucleophilic O-substitution reaction; 4-O-substituted phenylcarbonyls; 4-O-substituted chalcones; Anticancer activity
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Funding
- TUBITAK-BIDEB-Funding of Visiting Scientists on Sabbatical Leave Fellowship Program [2221]
- Alexander von Humboldt Foundation [3.4 - 8151/Kuete, 19014, 3.4 - 8151 / 18026]
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A new series of O-substituted chalcone derivatives with different substituents were designed, synthesized, and characterized, showing promising cytotoxic effects against leukemia and colon adenocarcinoma cells in preliminary cytotoxicity tests.
A new series of O-substituted chalcone derivatives bearing an/a allyl-, prenyl- or propargyl-substituent at different positions of rings A and B and their derivatives as drug leads, was designed, synthesized, and characterized. The chalcone derivatives were synthesized via base catalyzed Claisen-Schmidt condensation in MeOH or EtOH solutions of appropriately substituted aromatic ketones with O-allyl, and O-propargylvanillin, respectively. The intermediates O-substituted phenylketone derivatives were firstly synthesized by nucleophilic substitution reaction. All the newly synthesized compounds were characterized by IR, NMR spectral data and elemental analyses. A preliminary cytotoxicity was performed with the compounds (1a, 1b, 2a, 2b, 3a, 3b, 4a, Sa-f, 6a-d, 7a-d) and the positive control, doxorubicin towards CCRF-CEM leukemia cells. Amongst them, compounds 1a, 2a, 5b-d, 6b, 7a, 7c and doxorubicin displayed IC50 values below 20 mu M while other compounds were less or not active at up to 50 mu M. Remarkably interesting cytotoxic effects, with IC50 values below 1 mu M were recorded with 5c against HCT116p53(-/-) colon adenocarcinoma cells, Se against CCRF-CEM cells and MDA-MB-231-BCRP breast adenocarcinoma cells, and 6b against HCT116 p53(+/+) cells and HCT116 p53(-/-) cells.
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