European Journal of Chemistry

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

Main Article Content

Moustafa Ahmed Gouda
Majed Musallam Mutlaq Al‐Balawi
Ameen Ali Abu-Hashem


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.

icon graph This Abstract was viewed 1671 times | icon graph Article PDF downloaded 772 times

How to Cite
Gouda, M. A.; Al‐Balawi, M. M. M.; Abu-Hashem, A. 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, 363-367.

Article Details

Crossref - Scopus - Google - European PMC

[1]. Gutteridge, J. M. C. Free Radic. Res. Commun. 1993, 19, 141-158.

[2]. Kehrer, J. P. Crit. Rev. Toxicol. 1993, 23, 21-48.

[3]. Becker, L. B. Cardiovasc. Res. 2004, 61, 461-470.

[4]. Hayes, J. D.; McLellan, L. I. Free Radic. Res. 1999, 31, 273-300.

[5]. Masella, R.; Di Benedetto, R.; Vari, R.; Filesi, C.; Giovannini, C. J. Nutr. Biochem. 2005, 16, 577-586.

[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.

[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.

[8]. Kessler, P.; Aybek, T.; Neidhart, G.; Dogan, S.; Lischke, V.; Bremerich, D. H.; Byhahan, C. J. Cardiothorac. Vasc. Anesth. 2005, 19, 32-39.

[9]. Sugiura, S.; Ohno, S.; Ohtani, O.; Izumi, K.; Kitamikado, T.; Asai, H.; Kato, K. J. Med. Chem. 1977, 20, 80-85.

[10]. Bailey, D. M.; Hansen, P. E.; Hlavac, A. G.; Baizman, E. R.; Pearl, J. J. Med. Chem. 1985, 28, 256-260.

[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.<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.

[18]. Buzykin, I.; Lonshchakova, T. I. Russ. Chem. B+ 1971, 20, 2224-2226.

[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.

[23]. Elinson, M. N.; Dorofeev, A. S.; Nasybullin, R. F.; Nikishin, G. I. Synthesis 2008, 12, 1933-1937.

[24]. Sujatha, K.; Shanthi, G.; Selvam, N. P.; Manoharan, S.; Perumal, P. T.; Rajendran, M.; Bioorg. Med. Chem. Lett. 2009, 19, 4501-4503.

[25]. Niknam, K.; Saberi, D.; Sadegheyan, M.; Deris, A. Tetrahedron Lett. 2010, 51, 692-694.

[26]. Zang, H.; Su, Q.; Mo, Y.; Cheng, B. Ultrason. Sonochem. 2011, 18, 68-72.

[27]. Babaie, M.; Sheibani, H. Arab. J. Chem. 2011, 4, 159-162.

[28]. Sobhani, S.; Hasaninejad, A. R.; Maleki M. F; Parizi Z. P. Synth. Commun. 2012, 42, 2245-2255.

[29]. Sobhani, S.; Safaei, E.; Hasaninejad, A. R.; Rezazadeh, S. J. Organomet. Chem. 2009, 694, 3027-3031.

[30]. Gouda, M. A. J. Heterocyclic Chem. 2016, 53, 356-376.

[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.

[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.

[36]. Karimi-Jaberi, Z.; Pooladian, B.; Moradi, M.; Ghasemi, E. Chin. J. Catal. 2012, 33, 1945-1949

[37]. Lissi, E. A.; Modak, B.; Torres, R.; Esocbar, J.; Urzua, A. Free Radic. Res. 1999, 30(6), 471-477.

[38]. Gutteridge, J.; Rowley, D.; Halliwell, B. Biochem. J. 1981, 199, 263-265.

[39]. Abdel-Wahab, B. F.; El-Ahl A. A.; Badria F. A Chem. Pharm. Bull. 2009, 57, 1348-1351

[40]. Gouda, M. A. J. Heterocyclic. Chem. 2015, DOI: 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.

Supporting Agencies

Most read articles by the same author(s)

Dimensions - Altmetric - scite_ - PlumX

Downloads and views


Download data is not yet available.


Metrics Loading ...
License Terms

License Terms


Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License ( By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License ( are administered by Atlanta Publishing House LLC (European Journal of Chemistry).