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3‐(2‐(5‐Amino‐3‐aryl‐1 H ‐pyrazol‐1‐yl) thiazol‐4‐yl)‐2 H ‐chromen‐2‐ones as Potential Anticancer Agents: Synthesis, Anticancer Activity Evaluation and Molecular Docking Studies
Author(s) -
Vaarla Krishnaiah,
Karnewar Santosh,
Panuganti Devayani,
Peddi Saikiran Reddy,
Vedula Rajeswar Rao,
Manga Vijjulatha,
Kotamraju Srigiridhar
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900077
Subject(s) - hela , chemistry , aryl , stereochemistry , docking (animal) , proton nmr , potency , cancer cell lines , cancer cell , combinatorial chemistry , cell culture , in vitro , cancer , biochemistry , organic chemistry , biology , medicine , alkyl , nursing , genetics
In an effort to design and develop efficient anticancer agents here, we report the synthesis, anticancer activity and molecular docking studies of new 3‐(2‐(5 amino‐3‐aryl‐1 H ‐pyrazol‐1‐yl)thiazol‐4‐yl)‐2 H ‐chromen‐2‐ones. The target products were synthesized via a facile one pot multicomponent approach by utilizing various substituted 3‐(2‐bromoacetyl)coumarins( 1 a‐j ), thiosemicarbazide ( 2 ) and benzoylacetonitriles ( 3 a–c ) with excellent yields. All the synthesized compounds were characterized by physical and analytical methods (IR, 1 H NMR, 13 C NMR and Mass spectra) and screened for their anti cancer property against five human cancer cell lines [L1210, CEM, DU‐145, HeLa, and MCF‐7]. Among the tested compounds, 6‐diethylamino substituted compound 4 k exhibited excellent potency against tested cancer cell lines, whereas 6,8‐Ditert‐butyl substituted compound 4 j shown promising activity against DU‐145 and MCF‐7 cancer cell lines with IC 50 values of 7±1 and 9±6 μM. Molecular docking study was carried out in order to understand the most plausible binding site interactions of the compounds with human Epidermal growth factor receptor (EGFR).