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Design and Synthesis of Novel Fluorescent 2-(aryloxy)-3-(4,5-diaryl)-1H-imidazol-2-yl)quinolines: Solvatochromic, DFT, TD-DFT Studies, COX-1 and COX-2 Inhibition and Antioxidant Properties

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Abstract

The present work focuses on the synthesis of novel heterocycles 2-(aryloxy)-3-(4,5-diaryl-1H-imidazol-2-yl)quinolines (6k-v) by an effective condensation reaction. These molecules exhibited fluorescent properties and hence for the proper understanding of their optical behavior and quantum yields, solvatochromic studies have been carried out. Further, frontier molecular orbitals, molecular electrostatic potential (MEP), and geometrical structure optimization have been investigated using the B3LYP/6-311G ++ (d, p) method. The energy gap between the HOMO, LUMO of the optical and energy band gap is determined by DFT and UV–visible spectra for TD-DFT studies are done. The screening of these compounds for in vitro COX-1 and COX-2 inhibition and DPPH free radical scavenging ability assays produced promising results. The binding interactions of these molecules against the COX-2 enzyme (PDB: 5IKR) were validated by docking studies.

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Acknowledgements

The authors thank DST, New Delhi (SAIF program) and the University Scientific Instrumentation Centre (USIC), Karnatak University, Dharwad, India for providing NMR, UV-Visible, Fluorescence, Powder X-ray, and EDX-SEM data. One of the authors (LB) thank University Grants Commission (UGC), Delhi for providing the Junior Research Fellowship.

Funding

The Junior Research Fellowship UGC Ref. No. 171/(CSIR-UGC NET JUNE 2019) was made available by the University Grants Commission (UGC), Delhi.

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Authors and Affiliations

  1. Department of Chemistry, Karnatak University, Dharwad, 580003, India

    Lokesh Bheemayya, Ravindra R. Kamble, Tukaram V. Metre & Barnabas Kodasi

  2. Department of Preclinical Research and Drug Development, Cytxon Biosolutions Pvt Ltd, Hubli, 580031, India

    Arun K. Shettar

  3. Department of Studies in Physics, Karnatak University, Dharwad, 580003, India

    Madivalagouda S. Sannaikar & Sanjeev R. Inamdar

  4. Department of Chemistry, Karnatak Science College, Dharwad, 580 003, India

    Mussuvir Pasha K. M

  5. Department of Bioinformatics and Biotechnology, Karnataka State Akkamahadevi Women’s University, Vijayapura, 586108, India

    Joy H. Hoskeri

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  1. Lokesh Bheemayya
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Contributions

Lokesh Bheemayya: Conceptualization; data curation; formal analysis; investigation; methodology; software; visualization. Ravindra R. Kamble: Formal analysis; investigation; project administration; resources; supervision. Arun K. Shettar: Data curation; formal analysis; validation; Tukaram V. Metre: Formal analysis; validation; visualization. Barnabas Kodasi: Formal analysis; validation; visualization. Madivalagouda S. Sannaikar: Data curation; formal analysis; validation. Sanjeev R. Inamdar: Data curation; formal analysis; validation. Mussuvir Pasha K. M: Data curation; formal analysis; validation. Joy H. Hoskeri: Data curation; formal analysis; Validation.

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Bheemayya, L., Kamble, R.R., Shettar, A.K. et al. Design and Synthesis of Novel Fluorescent 2-(aryloxy)-3-(4,5-diaryl)-1H-imidazol-2-yl)quinolines: Solvatochromic, DFT, TD-DFT Studies, COX-1 and COX-2 Inhibition and Antioxidant Properties. J Fluoresc (2023). https://doi.org/10.1007/s10895-023-03418-6

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