Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity
نویسندگان
چکیده
Abstract Seven novel azo dyes with 2-pyridone and dihydropyrimidinone moieties have been synthesized thoroughly characterized. The azo-hydrazone tautomerism has investigated by experimental theoretical approaches. optimizations of geometries performed density functional theory (DFT). vibrational NMR spectra were calculated correlated ones. Furthermore, quantum chemical descriptors MEP maps plotted to determine biological reactivity dyes. antioxidant assay evinced that 5, 6 7 are promising candidates. In vitro cytotoxic activity was studied against three malignant cell lines: prostate adenocarcinoma (PC-3), lung carcinoma (A549) chronic myelogenous leukemia (K562), as well human normal fibroblasts (MRC-5), using MTT assay. Examination effects on cancer lines showed the concentration dependent cytotoxicity all compounds. K562 cells most sensitive compounds 3, 5 6, wherein compound particularly prominent selective in action between K562 (24.97 ?M) PC-3 (48.98 ?M) cells, MRC-5 (91.11 ?M) cells. Moreover, cycle analysis examined K562 cells, flow cytometry, study its mechanism anticancer action. Finally, silico evaluation physicochemical parameters, druglikeness ADME properties orally bioavailable no permeation blood brain barrier.
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ژورنال
عنوان ژورنال: Dyes and Pigments
سال: 2021
ISSN: ['1873-3743', '0143-7208']
DOI: https://doi.org/10.1016/j.dyepig.2020.109123