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Synthesis and characterization of new 4-aryl-2-(2-oxopropoxy)-6-(2,5-dichlorothiophene)nicotinonitrile and their furo[2,3-b]pyridine derivatives: Assessment of antioxidant and biological activity
Mahmoud Al‐Refai (1,*)
, Mohammad Ibrahim (2) , Abdullah Al‐Fawwaz (3) , Armin Geyer (4) (1) Department of Chemistry, Faculty of Science, Al Al-Bayt University, Al-Mafraq, 25113, Jordan
(2) Department of Chemistry, Faculty of Science, Al Al-Bayt University, Al-Mafraq, 25113, Jordan
(3) Department of Biological Sciences, Faculty of Science, Al Al-Bayt University, Al-Mafraq, 25113, Jordan
(4) Faculty of Chemistry, Philipps University Marburg, Hans-Meerwein-Straße 4, 35032 Marburg, Germany
(*) Corresponding Author
Received: 27 Sep 2018 | Revised: 18 Oct 2018 | Accepted: 20 Oct 2018 | Published: 31 Dec 2018 | Issue Date: December 2018
Abstract
A new series of furo[2,3-b]pyridine derivatives bearing aryl substituents were synthesized in two steps, where, the cyano-(2H)-pyridones (1a-l) were converted to the corresponding nicotinonitriles (2a-l), followed by the Thorpe-Ziegler ring cyclization to the furo[2,3-b]pyridine derivatives (3a-l). All new compounds were characterized by 1D-NMR experiments (1H and 13C) and 2D-NMR experiments (COSY, HMBC and HSQC), as well as ESI-MS and HR-ESI-MS data. The new compounds were screened for their antioxidant activities by 2,2-diphenyl-1-picryl-hydrazylhydrate (DPPH) free radical assay. The highest radical scavenging effect was observed for nicotinonitriles 2d, 2h and 2l and furo[2,3-b]pyridines 3b, 3f and 3j by methanolic solvent at 4.0 mg/mL concentration. Remarkably, all nicotinonitriles and furo[2,3-b]pyridine exhibited a significant radical scavenging activity after 24 and 48 hours compared with 0.5 hour.
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DOI: 10.5155/eurjchem.9.4.375-381.1792
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Funding information
We are grateful to Al Al-Bayt University (Mafraq, Jordan), and the Deutsche Forschungemeinschaft (DFG, Germany) for financial support.
Citations
[1]. Hanan A. Soliman, Ahmed H. Shamroukh, Eman R. Kotb, Khaled. Mahmoud, El Hassane. Anouar, Mohamed I. Hegab
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[2]. Mohammad M. Ibrahim, Mahmoud Al-Refai, Mohamad Nurul Azmi, Hasnah Osman, Mohamad Hafizi Abu Bakar, Armin Geyer
Synthesis, characterization and cytotoxicity of new nicotinonitriles and their furo[2,3-b]pyridine derivatives
Journal of the Iranian Chemical Society 16(4), 715, 2019
DOI: 10.1007/s13738-018-1549-y
[3]. Rasha K. Abuflaha, Fakhri O. Yousef, Raed Ghanem, Khaldoun Al-Sou’od, Ihsan A. Shahdi, Omar K. Almashaqbeh, Mahmoud Al-Refai
Investigation of Solvent Effect and H-Bonding on Spectroscopic Properties of 1-(3-Amino-6-(2,5-dichlorothiophen-3-yl)-4-phenylfuro[2,3-b]Pyridin-2-yl) Ethenone: Experimental and Computational Study
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[4]. Sherif M. H. Sanad, Ahmed E. M. Mekky
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[6]. Al-Refai, Ibrahim, Azmi, Osman, Bakar, Geyer
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DOI: 10.3390/molecules24224072
[7]. Mohammad M. Ibrahim, Hasan Abumahmoud, Abdullah T. Al-Fawwaz
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DOI Link: https://doi.org/10.5155/eurjchem.9.4.375-381.1792
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European Journal of Chemistry 2018, 9(4), 375-381 | doi: https://doi.org/10.5155/eurjchem.9.4.375-381.1792 | Get rights and content
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