Iodine catalyzed simple and efficient synthesis of antiproliferative 2-pyridones
| Autor: | Komuraiah Buduma, Niranjana Kumar Arigari, K.V.N.S. Srinivas, Srinivas Chinde, Paramjit Grover, J. Kotesh Kumar |
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| Rok vydání: | 2016 |
| Předmět: |
Pyridones
Clinical Biochemistry Pharmaceutical Science chemistry.chemical_element Antineoplastic Agents Apoptosis 010402 general chemistry Iodine 01 natural sciences Biochemistry Catalysis chemistry.chemical_compound Cell Line Tumor Drug Discovery medicine Humans Topoisomerase II Inhibitors Doxorubicin Molecular Biology IC50 A549 cell Caspase 3 010405 organic chemistry Chemistry Organic Chemistry Caspase 9 0104 chemical sciences DNA Gyrase Cell culture Pyran Cancer cell Molecular Medicine Drug Screening Assays Antitumor Nuclear chemistry medicine.drug |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 26:2159-2163 |
| ISSN: | 0960-894X |
| Popis: | A simple and efficient method for the selective synthesis of 2-pyrdones from 4H-pyrans using iodine as catalyst and ethanol as solvent was developed. The present method is equally effective for both aromatic and hetero aromatic ring containing 4H-pyrans. The compatibility with various functional groups, mild reaction conditions, high yields and application of inexpensive, readily and easily available iodine as catalyst and formation of 2-pyridones as major products are the advantages of the present procedure. In vitro antiproliferative activity of the final synthesized compounds was evaluated with four different human cancer cell lines (Lung adenocarcinoma-A549, Hepatocarcinoma-HepG2, Breast carcinoma-MCF-7 and Ovarian carcinoma-SKOV3) and normal human lung fibroblast cell line (MRC-5). Compounds 2b showed better inhibition against MCF-7, HepG2 and A549 cell lines (IC50 8.00 ± 0.11, 11.93 ± 0.01 and 15.85 ± 0.04 μM, respectively) as compared with doxorubicin and also 2e showed moderate inhibition against MCF-7, HepG2 (IC50 9.32 ± 0.21 and 20.22 ± 0.01 μM, respectively, cell lines, respectively) as compared with doxorubicin. As many clinically used antiproliferative agents induce apoptosis in cancer cells hence, the 2-pyridone analogues were also tested for their ability to induce apoptosis in MCF-7 cells using the caspases-3 and -9 assays. |
| Databáze: | OpenAIRE |
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