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Ultrasound-promoted convenient and ionic liquid [BMIM]BF4 assisted green synthesis of diversely functionalized pyrazolo quinoline core via one-pot multicomponent reaction, DFT study and pharmacological evaluation

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Abstract

An ultrasound-assisted green protocol for one-pot synthesis of a new series of pharmaceutically relevant pyrazolo quinoline derivatives (4a–t) were synthesized, characterized, and evaluated using DFT and biological activities. Pyrazolo quinoline derivatives (4a–t) were synthesized via a three-component tandem reaction of 1,3-dicarbonyl compound (1a–b), substituted aromatic aldehyde (2a–o), and 5-amino indazole (3a) in the presence of 1-butyl-3-methylimidazolium tetrafluoroborate [BMIM]BF4 ionic liquid in ethanol at ambient conditions. The main purpose of the present work is selective functionalization of pyrazolo quinoline (4a–t) core excluding another potential parallel reaction under environmentally benign reaction conditions. The present protocol shows features such as amphiphilic behavior of ionic liquid during reaction transformation, and reusability of the [BMIM]BF4 ionic liquid under mild reaction condition. All newly derived compounds were evaluated for their in vitro anti-inflammatory and antioxidant activity. Among them, compound 4c showed encouraging antioxidant activity compared with standard antioxidant ascorbic acid, and compounds 4n and 4r displayed very good anti-inflammatory activity compared with a standard drug. In this study, a theoretical computational density functional study was also executed to perform the geometry optimizations, frontier molecular orbital approach, and molecular electrostatic potential (MESP). The DFT study was carried out with the basis set DFT/B3LYP/6-31+G (d, p) level of theory. The quantum chemical descriptors (QCDS) and MESP diagrams were plotted to examine the biological reactivities of representative pyrazolo quinolines (4a–t).

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Acknowledgements

This research was supported by the Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Gujarat, India. All the authors are grateful to UGC, New Delhi for UGC-CPEPA Phase-II program sponsored under award letter no. F. No. 1-14/2002-2016 (NS/PE) dated 28 April, 2016, as well as UGC-CAS, Phase-II sponsored under award latter no. F-540/5/CASII/2018 (SAP-I) dated 25 July, 2018 for the assistance in general. We also thankful to Microbiology Department of R. C. Patel A. S. C College, Shirpur, Maharashtra, India for the biological screening of the compounds reported herein. The authors are also thankful to SynZeal Research Pvt. Ltd. Ahmedabad for analytical testing. One of the authors (Dipakkumar D. Chudasama) is grateful to the SHODH-ScHeme of Developing High quality research, student Ref No: 202001640021, Education Department, Gujarat State.

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  1. Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Anand, 388120, Gujarat, India

    Dipakkumar D. Chudasama, Manan S. Patel, Jaydeepkumar N. Parekh, Harsh C. Patel, Chetan V. Rajput, Navin P. Chikhaliya & Kesur R. Ram

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Chudasama, D.D., Patel, M.S., Parekh, J.N. et al. Ultrasound-promoted convenient and ionic liquid [BMIM]BF4 assisted green synthesis of diversely functionalized pyrazolo quinoline core via one-pot multicomponent reaction, DFT study and pharmacological evaluation. Mol Divers 27, 1409–1425 (2023). https://doi.org/10.1007/s11030-022-10498-2

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