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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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,*) orcid , Mohammad Ibrahim (2) orcid , Abdullah Al‐Fawwaz (3) orcid , Armin Geyer (4) orcid

(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.


Keywords


Pyridine; Thiophene; Antioxidant; Nicotinonitrile; Cyanopyridone; Furo[2,3-b]pyridine

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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

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[1]. 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
/


[2]. Sherif M. H. Sanad, Ahmed E. M. Mekky
Synthesis, in-vitro antibacterial and anticancer screening of novel nicotinonitrile-coumarin hybrids utilizing piperazine citrate
Synthetic Communications  50(10), 1468, 2020
DOI: 10.1080/00397911.2020.1743318
/


[3]. Al-Refai, Ibrahim, Azmi, Osman, Bakar, Geyer
The Synthesis, Characterization, Cytotoxic Activity Assessment and Structure–Activity Relationship of 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-2-methoxypyridine-3-carbonitriles
Molecules  24(22), 4072, 2019
DOI: 10.3390/molecules24224072
/


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How to cite


Al‐Refai, M.; Ibrahim, M.; Al‐Fawwaz, A.; Geyer, A. Eur. J. Chem. 2018, 9(4), 375-381. doi:10.5155/eurjchem.9.4.375-381.1792
Al‐Refai, M.; Ibrahim, M.; Al‐Fawwaz, A.; Geyer, A. 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. Eur. J. Chem. 2018, 9(4), 375-381. doi:10.5155/eurjchem.9.4.375-381.1792
Al‐Refai, M., Ibrahim, M., Al‐Fawwaz, A., & Geyer, A. (2018). 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. European Journal of Chemistry, 9(4), 375-381. doi:10.5155/eurjchem.9.4.375-381.1792
Al‐Refai, Mahmoud, Mohammad Ibrahim, Abdullah Al‐Fawwaz, & Armin Geyer. "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." European Journal of Chemistry [Online], 9.4 (2018): 375-381. Web. 3 Aug. 2020
Al‐Refai, Mahmoud, Ibrahim, Mohammad, Al‐Fawwaz, Abdullah, AND Geyer, Armin. "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" European Journal of Chemistry [Online], Volume 9 Number 4 (31 December 2018)

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DOI Link: https://doi.org/10.5155/eurjchem.9.4.375-381.1792

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