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

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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.


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).

2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).

3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).


Editor-in-Chief
European Journal of Chemistry

Keywords


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

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.7.3.363-367.1474

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1505 times | icon graph PDF Article downloaded 698 times


Citations

/


[1]. Pankaj Teli, Nusrat Sahiba, Anu Manhas, Prakash C. Jha, Priyadarshi Meena, Shikha Agarwal
Synthetic Access to Bis(pyrazolyl)methanes using cost‐efficient Triethylammonium Hydrogen Sulfate Ionic Liquid: Evaluation of Antioxidant Activity via in silico and in vitro Studies
ChemistrySelect  8(15), , 2023
DOI: 10.1002/slct.202204806
/


[2]. 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
/


[3]. 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
/


[4]. 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  127, 106001, 2022
DOI: 10.1016/j.bioorg.2022.106001
/


[5]. 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
/


[6]. Anant B. Kanagare, M.Sc.Ashok R. Yadav, Ashishkumar P. Katariya, Devidas S. Bhagat, Ajit K. Dhas, Dattatraya N. Pansare, Pratik A. Nagwade, Brajesh Kumar, Jaiprakash N. Sangshetti, Satish U. Deshmukh
Insights into 4,4′‐Arylmethylene‐Bis‐1H‐Pyrazol‐5‐Ols Scaffolds: Various Synthetic Routes and Their Applications
ChemistrySelect  8(4), , 2023
DOI: 10.1002/slct.202204088
/


[7]. Andrzej Danel, Elżbieta Porębska, Kacper Markiel, Oleksii Havrysh, Mateusz Kucharek, Arkadiusz Gut, Tomasz Uchacz
Multicomponent Synthesis of 4-Aryl-4,9-dihydro-1H-pyrazolo[3,4-b]quinolines Using L-Proline as a Catalyst—Does It Really Proceed?
Molecules  28(22), 7612, 2023
DOI: 10.3390/molecules28227612
/


[8]. Michail N. Elinson, Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Varvara M. Kalashnikova, Oleg I. Maslov
Stereoselective and efficient chemical transformation of aldehydes and two molecules of pyrazolin-5-one into bis(spiropyrazolone)cyclopropanes under a column chromatography-free protocol at room temperature
Monatshefte für Chemie - Chemical Monthly  154(6), 625, 2023
DOI: 10.1007/s00706-023-03072-5
/


[9]. 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
/


References


[1]. Gutteridge, J. M. C. Free Radic. Res. Commun. 1993, 19, 141-158.
http://dx.doi.org/10.3109/10715769309111598

[2]. Kehrer, J. P. Crit. Rev. Toxicol. 1993, 23, 21-48.
http://dx.doi.org/10.3109/10408449309104073

[3]. Becker, L. B. Cardiovasc. Res. 2004, 61, 461-470.
http://dx.doi.org/10.1016/j.cardiores.2003.10.025

[4]. Hayes, J. D.; McLellan, L. I. Free Radic. Res. 1999, 31, 273-300.
http://dx.doi.org/10.1080/10715769900300851

[5]. Masella, R.; Di Benedetto, R.; Vari, R.; Filesi, C.; Giovannini, C. J. Nutr. Biochem. 2005, 16, 577-586.
http://dx.doi.org/10.1016/j.jnutbio.2005.05.013

[6]. Hartmann, R. E.; Shah, A.; Fagan, A. M.; Schwetye, K. E.; Parsadanian, M.; Schulman, R. N.; Finn, M. B.; Holtzman, D. M. Neurobiol. Dis. 2006, 24, 506-515.
http://dx.doi.org/10.1016/j.nbd.2006.08.006

[7]. Elguero, J. In Comprehensive Heterocyclic Chemistry: Pyrazoles and their Benzo Derivatives, Vol. 5, ed. by Katritzky, A. R. and Rees, C. W., Pergamon Press, Oxford, 1984, 167-303.
http://dx.doi.org/10.1016/B978-008096519-2.00072-2

[8]. Kessler, P.; Aybek, T.; Neidhart, G.; Dogan, S.; Lischke, V.; Bremerich, D. H.; Byhahan, C. J. Cardiothorac. Vasc. Anesth. 2005, 19, 32-39.
http://dx.doi.org/10.1053/j.jvca.2004.11.006

[9]. Sugiura, S.; Ohno, S.; Ohtani, O.; Izumi, K.; Kitamikado, T.; Asai, H.; Kato, K. J. Med. Chem. 1977, 20, 80-85.
http://dx.doi.org/10.1021/jm00211a016

[10]. Bailey, D. M.; Hansen, P. E.; Hlavac, A. G.; Baizman, E. R.; Pearl, J. J. Med. Chem. 1985, 28, 256-260.
http://dx.doi.org/10.1021/jm00380a020

[11]. Mahajan, R. N.; Havaldar, F. H.; Fernandes, P. S. J. Indian Chem. Soc. 1991, 68, 245-246.

[12]. Chauhan, P. M. S.; Singh, S.; Chatterjee, R. K. Ind. J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1993, 32, 858-861.

[13]. Singh, D.; Singh, D. J. Ind. Chem. Soc. 1991, 68, 165-167.

[14]. Londershausen, M. Pestic. Sci. 1996, 48, 269-292.
http://dx.doi.org/10.1002/(SICI)1096-9063(199612)48:4<269::AID-PS478>3.0.CO;2-B

[15]. The Chemistry of Synthetic Dyes and Pigments; H. A. Lube (Ed. ); American Chemical Society: Washington, DC, 1970

[16]. Garnovskii, A. D.; Uraev, A. I.; Minkin, V. I. Arkivoc 2004, 3, 29-41.

[17]. Pavlov, T.; Goleneva, A. F.; Lesnov, A. E.; Prokhorova, T. S. Pharm. Chem. J. 1998, 32, 370-372.
http://dx.doi.org/10.1007/BF02645994

[18]. Buzykin, I.; Lonshchakova, T. I. Russ. Chem. B+ 1971, 20, 2224-2226.
http://dx.doi.org/10.1007/BF00851295

[19]. Li, L.; Ma, H.; Wang, Y. M.; Meng, J. B. Chem. J. Chin. Univ. 1995, 12, 1903-1910.

[20]. Bai, J.; Lu, J.; Wang, Z. J.; Gan, H. Y.; Ma, H. R. Chin. J. Org. Chem. 2004, 6, 616-620.

[21]. Shi, D. Q.; Chen, J.; Wu, B.N.; Zhuang, Q. Y.; Wang, X. S. Chin. J. Org. Chem. 2005, 25, 405-408.

[22]. Wang, W.; Wang, S. X.; Qin, X. Y.; Li, J. T. Synth. Commun. 2005, 9, 1263-1269.
http://dx.doi.org/10.1081/SCC-200054854

[23]. Elinson, M. N.; Dorofeev, A. S.; Nasybullin, R. F.; Nikishin, G. I. Synthesis 2008, 12, 1933-1937.
http://dx.doi.org/10.1055/s-2008-1067079

[24]. Sujatha, K.; Shanthi, G.; Selvam, N. P.; Manoharan, S.; Perumal, P. T.; Rajendran, M.; Bioorg. Med. Chem. Lett. 2009, 19, 4501-4503.
http://dx.doi.org/10.1016/j.bmcl.2009.02.113

[25]. Niknam, K.; Saberi, D.; Sadegheyan, M.; Deris, A. Tetrahedron Lett. 2010, 51, 692-694.
http://dx.doi.org/10.1016/j.tetlet.2009.11.114

[26]. Zang, H.; Su, Q.; Mo, Y.; Cheng, B. Ultrason. Sonochem. 2011, 18, 68-72.
http://dx.doi.org/10.1016/j.ultsonch.2010.08.001

[27]. Babaie, M.; Sheibani, H. Arab. J. Chem. 2011, 4, 159-162.
http://dx.doi.org/10.1016/j.arabjc.2010.06.032

[28]. Sobhani, S.; Hasaninejad, A. R.; Maleki M. F; Parizi Z. P. Synth. Commun. 2012, 42, 2245-2255.
http://dx.doi.org/10.1080/00397911.2011.555589

[29]. Sobhani, S.; Safaei, E.; Hasaninejad, A. R.; Rezazadeh, S. J. Organomet. Chem. 2009, 694, 3027-3031.
http://dx.doi.org/10.1016/j.jorganchem.2009.05.004

[30]. Gouda, M. A. J. Heterocyclic Chem. 2016, 53, 356-376.
http://dx.doi.org/10.1002/jhet.2313

[31]. Hassankhani, A. J. Mex. Chem. Soc. 2015, 59(1), 1-4.

[32]. Kimata, A.; Nakagawa, H.; Ohyama, R.; Fukuuchi, T.; Ohta, S.; Suzuki, T.; Miyata. N. J. Med. Chem. 2007, 50, 5053-5056.
http://dx.doi.org/10.1021/jm070688r

[33]. Porai-Koshits, A. E.; Porai-Koshits, B. A.; Lipina, N. G. Zh. Obshch. Khim. 1956, 26, 872-877.

[34]. Ahluwalia, V. K.; Sharma, P.; Goyal, B. A. Indian J. Chem. B 1997, 36, 1059-1061

[35]. Hasaninejad, A.; Zare, A.; Shekouhy, M. Golzar, N. Org. Prep. Proced. Int. 2011, 43, 131-137.
http://dx.doi.org/10.1080/00304948.2010.526827

[36]. Karimi-Jaberi, Z.; Pooladian, B.; Moradi, M.; Ghasemi, E. Chin. J. Catal. 2012, 33, 1945-1949
http://dx.doi.org/10.1016/S1872-2067(11)60477-4

[37]. Lissi, E. A.; Modak, B.; Torres, R.; Esocbar, J.; Urzua, A. Free Radic. Res. 1999, 30(6), 471-477.
http://dx.doi.org/10.1080/10715769900300511

[38]. Gutteridge, J.; Rowley, D.; Halliwell, B. Biochem. J. 1981, 199, 263-265.
http://dx.doi.org/10.1042/bj1990263

[39]. Abdel-Wahab, B. F.; El-Ahl A. A.; Badria F. A Chem. Pharm. Bull. 2009, 57, 1348-1351
http://dx.doi.org/10.1248/cpb.57.1348

[40]. Gouda, M. A. J. Heterocyclic. Chem. 2015, DOI: 10.1002/jhet.2576.
http://dx.doi.org/10.1002/jhet.2576

[41]. Metwally, M. A.; Gouda, M. A.; Harmal, A. N.; Khalil, A. M. Eur. J. Med. Chem. 2012, 56, 254-62.
http://dx.doi.org/10.1016/j.ejmech.2012.08.034


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. 10 Dec. 2023
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)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.7.3.363-367.1474


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



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

Refbacks

  • There are currently no refbacks.




Copyright (c)





© Copyright 2010 - 2023  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.