European Journal of Chemistry 2016, 7(3), 363-367 | doi: https://doi.org/10.5155/eurjchem.7.3.363-367.1474 | Get rights and content

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One-pot pseudo five-component synthesis and antioxidant evaluation of 4,4'-(aryl-methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)


Moustafa Ahmed Gouda (1,*) , Majed Musallam Mutlaq Al‐Balawi (2) , Ameen Ali Abu-Hashem (3)

(1) Chemistry Department, Faculty of Science, Mansoura University, Mansoura 35516, Egypt
(2) Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
(3) Department of Photochemistry, National Research Center, Dokki, Giza 12622, Egypt
(*) Corresponding Author

Received: 09 Jul 2016 | Revised: 14 Jul 2016 | Accepted: 23 Jul 2016 | Published: 30 Sep 2016 | Issue Date: September 2016

Abstract


A simple method for the synthesis of some 4,4'-(aryl-methylene)bis(3-methyl-1H-pyrazol-5-ol) derivatives via a one-pot pseudo five-component reaction of phenyl hydrazine, ethyl acetoacetate and aldehydes in acetic acid is reported. The prepared compounds were characterized by elemental analyses and spectral data. Some of the synthesized compounds were screened for their antioxidant activity using 2,2'-azino-bis(3-ethyl benzothiazoline-6-sulfonic acid (ABTS) method; all the investigated compounds showed similar and higher antioxidant activity than ascorbic acid and exhibited high protection against DNA damage induced by the bleomycin iron complex.


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Keywords


Arylmethylene; Bis-pyrazol-5-ol; Michael reaction; One pot reaction; Antioxidant activity; Tandem Knoevenagel reaction

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DOI: 10.5155/eurjchem.7.3.363-367.1474

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Citations

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[1]. Nader Ghaffari Khaligh, Taraneh Mihankhah, Hayedeh Gorjian, Mohd Rafie Johan
Greener and facile synthesis of 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s through a conventional heating procedure
Synthetic Communications  50(21), 3276, 2020
DOI: 10.1080/00397911.2020.1799014
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[2]. Mahdieh Sadeghpour, Abolfazl Olyaei
Recent advances in the synthesis of bis(pyrazolyl)methanes and their applications
Research on Chemical Intermediates  47(11), 4399, 2021
DOI: 10.1007/s11164-021-04592-7
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[3]. Daniele Florio, Valentina Roviello, Sara La Manna, Fabiana Napolitano, Anna Maria Malfitano, Daniela Marasco
Small molecules enhancers of amyloid aggregation of C-terminal domain of Nucleophosmin 1 in Acute Myeloid Leukemia
Bioorganic Chemistry  , 106001, 2022
DOI: 10.1016/j.bioorg.2022.106001
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[4]. Valentin G. Nenajdenko
Access to molecular complexity. Multicomponent reactions involving five or more components
Russian Chemical Reviews  89(11), 1274, 2020
DOI: 10.1070/RCR5010
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[5]. Nader Ghaffari Khaligh, Taraneh Mihankhah
Greener and practical synthesis of 4,4′‐(arylmethylene)bis( 3‐methyl‐1‐phenyl‐1H ‐pyrazol‐5‐ol)s through a conventional heating and a mechanochemical procedure
Journal of Heterocyclic Chemistry  57(11), 4036, 2020
DOI: 10.1002/jhet.4113
/


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How to cite


Gouda, M.; Al‐Balawi, M.; Abu-Hashem, A. Eur. J. Chem. 2016, 7(3), 363-367. doi:10.5155/eurjchem.7.3.363-367.1474
Gouda, M.; Al‐Balawi, M.; Abu-Hashem, A. One-pot pseudo five-component synthesis and antioxidant evaluation of 4,4'-(aryl-methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol). Eur. J. Chem. 2016, 7(3), 363-367. doi:10.5155/eurjchem.7.3.363-367.1474
Gouda, M., Al‐Balawi, M., & Abu-Hashem, A. (2016). One-pot pseudo five-component synthesis and antioxidant evaluation of 4,4'-(aryl-methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol). European Journal of Chemistry, 7(3), 363-367. doi:10.5155/eurjchem.7.3.363-367.1474
Gouda, Moustafa, Majed Musallam Mutlaq Al‐Balawi, & Ameen Ali Abu-Hashem. "One-pot pseudo five-component synthesis and antioxidant evaluation of 4,4'-(aryl-methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)." European Journal of Chemistry [Online], 7.3 (2016): 363-367. Web. 4 Jul. 2022
Gouda, Moustafa, Al‐Balawi, Majed, AND Abu-Hashem, Ameen. "One-pot pseudo five-component synthesis and antioxidant evaluation of 4,4'-(aryl-methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)" European Journal of Chemistry [Online], Volume 7 Number 3 (30 September 2016)

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