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Molecules 2017, 22(10), 1628; doi:10.3390/molecules22101628

Ionic Liquid-Catalyzed Green Protocol for Multi-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles as Potential Anticancer Scaffolds

1
Maulana Azad Post Graduate and Research Centre, Dr. Rafiq Zakaria Campus, Rauza Baug, Aurangabad 431001, India
2
Departamento de Química Orgánica, Facultad de Ciencias, Universidad of Santiago de Compostela, Alfonso X el Sabio, 27002 Lugo, Spain
3
Shreeyash Institute of Pharmaceutical Education and Research, Aurangabad 431010, India
4
Y.B. Chavan College of Pharmacy, Dr. Rafiq Zakaria Campus, Rauza Baug, Aurangabad 431001, India
*
Author to whom correspondence should be addressed.
Received: 1 August 2017 / Revised: 22 September 2017 / Accepted: 24 September 2017 / Published: 28 September 2017
(This article belongs to the Special Issue ECSOC-20)
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Abstract

A series of 6-amino-4-substituted-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles 5aj were synthesized via one-pot, four-component condensation reactions of aryl aldehydes 1aj, propanedinitrile (2), hydrazine hydrate (3) and ethyl acetoacetate (4) under solvent-free conditions. We report herein the use of the Brønsted acid ionic liquid (BAIL) triethylammonium hydrogen sulphate [Et3NH][HSO4] as catalyst for this multi-component synthesis. Compared with the available reaction methodology, this new method has consistent advantages, including excellent yields, a short reaction time, mild reaction conditions and catalyst reusability. Selected synthesized derivatives were evaluated for in vitro anticancer activity against four human cancer cell lines viz. melanoma cancer cell line (SK-MEL-2), breast cancer cell line(MDA-MB-231), leukemia cancer cell line (K-562) and cervical cancer cell line (HeLa). Compounds 5b, 5d, 5g, 5h and 5j exhibited promising anticancer activity against all selected human cancer cell lines, except HeLa. Molecular docking studies also confirmed 5b and 5d as good lead molecules. An in silico ADMET study of the synthesized anticancer agents indicated good oral drug-like behavior and non-toxic nature. View Full-Text
Keywords: ionic liquid; multi-component synthesis; dihydropyrano[2,3-c]pyrazoles; anticancer activity; ADMET prediction; molecular docking study ionic liquid; multi-component synthesis; dihydropyrano[2,3-c]pyrazoles; anticancer activity; ADMET prediction; molecular docking study
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Nimbalkar, U.D.; Seijas, J.A.; Vazquez-Tato, M.P.; Damale, M.G.; Sangshetti, J.N.; Nikalje, A.P.G. Ionic Liquid-Catalyzed Green Protocol for Multi-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles as Potential Anticancer Scaffolds. Molecules 2017, 22, 1628.

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