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Synthesis, anticancer evaluation, and docking studies of some novel azo chromene derivatives.
- Source :
-
Journal of the Chinese Chemical Society . Oct2020, Vol. 67 Issue 10, p1877-1886. 10p. - Publication Year :
- 2020
-
Abstract
- We have described a simple, convenient, and high‐yielding one‐pot synthesis of novel azo chromene derivatives via a three‐component reaction of various azo aldehydes with dimedone and malononitrile using 10 mol% of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) as catalyst and ethanol as solvent at reflux condition. All the synthesized compounds have been characterized using Fourier‐transform infrared spectroscopy (FT‐IR), 1H NMR, 13C NMR, and HR‐MS spectra and molecular docking was performed to explore new inhibitors of human placental aromatase cytochrome P450 and cyclooxygenase‐2 enzymes. Of all the compounds docked, compound (E)‐2‐amino‐4‐(4,4‐dimethyl‐2,6‐dioxocyclohexyl)‐6‐((3‐methoxyphenyl)diazenyl‐4H‐chromene‐3‐carbonitrile (4o) showed good binding affinity with the active site of human placental aromatase cytochrome P450 enzyme (PDB: 3EQM) with inhibition constant (Ki) 1.66 nM and compound 4o also showed good binding affinity with the active site of cyclooxygenase‐2 enzyme (PDB: 6COX) with inhibition constant (Ki) 367.17 pM. In vitro anti‐cancer activity studies against MCF‐7 cells were also performed for compounds 4o, anastrozole and celecoxib. Compound 4o showed an effective cytotoxicity at 19.8 μg/ml compared to anastrozole and celecoxib (24.7 and 26.2 μg/ml). [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00094536
- Volume :
- 67
- Issue :
- 10
- Database :
- Academic Search Index
- Journal :
- Journal of the Chinese Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 146677821
- Full Text :
- https://doi.org/10.1002/jccs.201900481