3‐(2‐(5‐Amino‐3‐aryl‐1H‐pyrazol‐1‐yl) thiazol‐4‐yl)‐2H‐chromen‐2‐ones as Potential Anticancer Agents: Synthesis, Anticancer Activity Evaluation and Molecular Docking Studies. Issue 14 (15th April 2019)

• Record Type: Journal Article
• Authors: Vaarla, Krishnaiah; Karnewar, Santosh; Panuganti, Devayani; Peddi, Saikiran Reddy; Vedula, Rajeswar Rao; Manga, Vijjulatha; Kotamraju, Srigiridhar
• Is Part Of: ChemistrySelect. Volume 4:Issue 14(2019)
• Page Start: 4324
• Page End: 4330
• Publication Date: 2019-04-15
• Subjects: Aminopyrazolylthiazoles, Anticancer activity, Coumarins, Molecular docking studies, Multicomponent reaction, .; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201900077
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: 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 compound4 k exhibited excellent potency against tested cancer cell lines, whereas 6, 8‐Ditert‐butyl substituted compound4 j shown promising activity against DU‐145 and MCF‐7 cancer cell lines with IC50 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). Abstract : A facile one pot multicomponent synthesis of 3‐(2‐(5‐amino‐3‐aryl‐1H‐pyrazol‐1‐yl)thiazol‐4‐yl)‐2H‐chromene‐2‐ones were obtained by utilizing various substituted 3‐(2‐bromoacetyl)coumarins(1a‐j), thiosemicarbazide (2) and benzoylacetonitriles (3 a‐c) with excellent yields in a shorter reaction time. All the synthesized compounds were characterized by physical and analytical methods and screened for their anti cancer property against five human cancer cell lines [L1210, CEM, DU‐145, HeLa, and MCF‐7].