Design, synthesis, characterization, and anticancer activity of a novel series of O-substituted chalcone derivatives
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, cilt.35, 2021 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 35
- Basım Tarihi: 2021
- Doi Numarası: 10.1016/j.bmcl.2021.127827
- Dergi Adı: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Chimica, EMBASE, MEDLINE, Veterinary Science Database
- Atatürk Üniversitesi Adresli: Evet
Özet
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.