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Synthesis of Fluorescent 1-(3-Amino-4-(4-(tert-butyl)phenyl)−6-(p-tolyl)furo[2,3-b]pyridin-2-yl)ethan-1-one: Crystal Structure, Fluorescence Behavior, Antimicrobial and Antioxidant Studies

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Abstract

Furopyridine III, namely 1-(3-amino-4-(4-(tert-butyl)phenyl)-6-(p-tolyl)furo[2,3-b]pyridin-2-yl)ethan-1-one, synthesized from 4-(4-(tert-butyl)phenyl)-2-oxo-6-(p-tolyl)-1,2-dihydropyridine-3-carbonitrile I in two steps. The title compound is characterized by NMR, MS and its X-ray structure. The molecular structure consists of planar furopyridine ring with both phenyl rings being inclined from the furopyridine scaffold to a significant different extent. There are three intramolecular hydrogen bonds within the structure. The lattice is stabilized by N—H…O, H2C—H …π and π…π intermolecular interactions leading to three-dimensional network. Compound III exhibits fluorescent properties, which are investigated. Antimicrobial potential and antioxidant activity screening studies for the title compound III and the heterocyclic derivatives, I and II, show no activity towards neither bacterial nor fungal strains, while they exhibited weak to moderate antioxidant activity compared to reference.

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Acknowledgements

The authors are grateful to Al Al-Bayt University (Mafraq, Jordan). The authors would like also to thank Professor Read Ghanem for his help in running the UV-visible spectra.

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Author notes

  1. Basem F. Ali

    Present address: Department of Chemistry, Faculty of Science, Al al-Bayt University, P.O. BOX 130040, Al-Mafraq, 25113, Jordan

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Al al-Bayt University, P.O. BOX 130040, Al-Mafraq, 25113, Jordan

    Mohammad M. Ibrahim & Mahmoud Al-Refai

  2. Department of Biological Sciences, Faculty of Science, Al al-Bayt University, Al-Mafraq, 25113, Jordan

    Abdullah Al-Fawwaz

  3. Department of Chemistry, King Faisal University, Al-Hasa, Saudi Arabia

    Basem F. Ali

  4. Faculty of Chemistry, Philipps University Marburg, Hans-Meerwein-Straße 4, 35032, Marburg, Germany

    Armin Geyer, Klaus Harms, Michael Marsch & Michelle Krüger

  5. School of Chemical Sciences, Universiti Sains Malaysia, 11800, Minden, Penang, Malaysia

    Hasnah Osman & Mohamad N. Azmi

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  1. Mohammad M. Ibrahim
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Correspondence to Mohammad M. Ibrahim.

Electronic supplementary material

ESM 1

CCDC 1816780 contains crystallographic data for compound III. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/getstructures, or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (44) 1223–336,033; or e-mail: deposit@ccdc.cam.ac.uk. (DOCX 676 kb)

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Ibrahim, M.M., Al-Refai, M., Al-Fawwaz, A. et al. Synthesis of Fluorescent 1-(3-Amino-4-(4-(tert-butyl)phenyl)−6-(p-tolyl)furo[2,3-b]pyridin-2-yl)ethan-1-one: Crystal Structure, Fluorescence Behavior, Antimicrobial and Antioxidant Studies. J Fluoresc 28, 655–662 (2018). https://doi.org/10.1007/s10895-018-2227-2

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