Microwave-assisted Synthesis of Novel Pyrazole Derivatives and their Biological Evaluation as Anti-Bacterial Agents

Hadis       Khodadad; Farhad       Hatamjafari; Khalil       Pourshamsian; Babak       Sadeghi

doi:10.2174/1386207323666201019152206

Abstract

Aims and Objectives: Microwave-assisted condensation of acetophenone 1 and aromatic aldehydes 2 gave chalcone analogs 3, which were cyclized to pyrazole derivatives 6a-f via the reaction with hydrazine hydrate and oxalic acid in the presence of the catalytic amount of acetic acid in ethanol.

Materials and Methods: The structural features of the synthesized compounds were characterized by melting point, FT-IR, ¹H, ¹³C NMR and elemental analysis.

Results: The antibacterial activities of the synthesized pyrazoles were evaluated against three gram-positive bacteria, such as Enterococcus durans, Staphylococcus aureus, Bacillus subtilis and two gram-negative bacteria such as Escherichia coli and Salmonella typhimurium.

Conclusion: All the synthesized pyrazoles showed relatively high antibacterial activity against S. aureus strain, and none of them demonstrated antibacterial activity against E. coli.

Keywords: Pyrazole, chalcone, microwave assisted, antibacterial, FT-IR, ¹H NMR, ¹³C NMR.

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[1] 
Balaban, A.T.; Oniciu, D.C.; Katritzky, A.R. Aromaticity as a cornerstone of heterocyclic chemistry. Chem. Rev.,  2004, 104(5), 2777-2812.
[http://dx.doi.org/10.1021/cr0306790] [PMID:  15137807] 
[2] 
Zeydi, M.M.; Mahmoodi, N.O. Overview on developed synthesis methods of triazepane heterocycles. J. Chin. Chem. Soc. (Taipei),  2017, 64, 1023-1034.
[http://dx.doi.org/10.1002/jccs.201700069] 
[3] 
Mahmoodi, N.O.; Zeydi, M.M.; Mamaghani, M.; Montazeri, N. Synthesis and antibacterial evaluation of several novel tripod pyrazoline with triazine core (TPTC) compounds. Res. Chem. Intermed.,  2017, 43, 2641-2651.
[http://dx.doi.org/10.1007/s11164-016-2786-2] 
[4] 
Hauptmann, S.; Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications, 2nd ed; John Wiley & Sons press, 2003, pp. 401-403.
[5] 
Wu, C.; Wang, J.; Zhang, X-Y.; Jia, G-K.; Cao, Z.; Tang, Z.; Yu, X.; Xu, X.; He, W-M. Palladium-catalyzed selective synthesis of 3,4-dihydroquinazolines from electron-rich arylamines, electron-poor arylamines and glyoxalates. Org. Biomol. Chem.,  2018, 16(27), 5050-5054.
[http://dx.doi.org/10.1039/C8OB01005F] [PMID:  29956708] 
[6] 
Gui, Q-W.; He, X.; Wang, W.; Zhou, H.; Dong, Y.; Wang, N.; Tang, J-X.; Cao, Z.; He, W-M. The clean preparation of multisubstituted pyrroles under metal- and solvent-free conditions. Green Chem.,  2020, 22, 118-122.
[http://dx.doi.org/10.1039/C9GC02657F] 
[7] 
Cao, Z.; Zhu, Q.; Lin, Y-W.; He, W-M. The concept of dual roles design in clean organic preparation. Chin. Chem. Lett.,  2019, 30, 2132-2138.
[http://dx.doi.org/10.1016/j.cclet.2019.09.041] 
[8] 
Ansari, A.; Ali, A.; Asif Shamsuzzaman, M. Review: biologically active pyrazole derivatives. New J. Chem.,  2016, 41, 16-41.
[http://dx.doi.org/10.1039/C6NJ03181A] 
[9] 
Kumar, V.; Kaur, K.; Gupta, G.K.; Sharma, A.K. Pyrazole containing natural products: synthetic preview and biological significance. Eur. J. Med. Chem.,  2013, 69, 735-753.
[http://dx.doi.org/10.1016/j.ejmech.2013.08.053] [PMID:  24099993] 
[10] 
Küçükgüzel, Ş.G.; Şenkardeş, S. Recent advances in bioactive pyrazoles. Eur. J. Med. Chem.,  2015, 97, 786-815.
[http://dx.doi.org/10.1016/j.ejmech.2014.11.059] [PMID:  25555743] 
[11] 
Wu, Y.; Tang, C.; Rui, R.; Yang, L.; Ding, W.; Wang, J.; Li, Y.; Lai, C.C.; Wang, Y.; Luo, R.; Xiao, W.; Zhang, H.; Zheng, Y.; He, Y. Synthesis and biological evaluation of a series of 2-(((5-akly/aryl-1H-pyrazol-3-yl)methyl)thio)-5-alkyl-6-(cyclohexylmethyl)-pyrimidin-4(3H)-ones as potential HIV-1 inhibitors. Acta Pharm. Sin. B,  2020, 10(3), 512-528.
[http://dx.doi.org/10.1016/j.apsb.2019.08.009] [PMID:  32140396] 
[12] 
Zampieri, D.; Mamolo, M.G.; Laurini, E.; Scialino, G.; Banfi, E.; Vio, L. Antifungal and antimycobacterial activity of 1-(3,5-diaryl-4,5-dihydro-1H-pyrazol-4-yl)-1H-imidazole derivatives. Bioorg. Med. Chem.,  2008, 16(8), 4516-4522.
[http://dx.doi.org/10.1016/j.bmc.2008.02.055] [PMID:  18321714] 
[13] 
Kumbar, M.N.; Kamble, R.R.; Dasappa, J.P.; Bayannavar, P.K.; Khamees, H.A.; Mahendra, M.; Joshi, S.D.; Dodamani, S.; Rasal, V.P.; Jalalpure, S. 5-(1-Aryl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)-1H-tetrazoles: Synthesis, structural characterization, Hirshfeld analysis, anti-inflammatory and anti-bacterial studies. J. Mol. Struct.,  2018, 116015, 63-72.
[http://dx.doi.org/10.1016/j.molstruc.2018.01.047] 
[14] 
Rai, N.P.; Narayanaswamy, V.K.; Shashikanth, S.; Arunachalam, P.N. Synthesis, characterization and antibacterial activity of 2-[1-(5-chloro-2-methoxy-phenyl)-5-methyl-1H-pyrazol-4-yl]-5-(substituted-phenyl)-[1,3,4]oxadiazoles. Eur. J. Med. Chem.,  2009, 44(11), 4522-4527.
[http://dx.doi.org/10.1016/j.ejmech.2009.06.020] [PMID:  19640616] 
[15] 
ElBordiny, H.S.; El-Miligy, M.M.; Kassab, S.E.; Daabees, H.; Mohamed Ali, W.A.; Abdelhamid Mohamed El-Hawash, S. Design, synthesis, biological evaluation and docking studies of new 3-(4,5-dihydro-1H-pyrazol/isoxazol-5-yl)-2-phenyl-1H-indole derivatives as potent antioxidants and 15-lipoxygenase inhibitors. Eur. J. Med. Chem.,  2018, 145, 594-605.
[http://dx.doi.org/10.1016/j.ejmech.2018.01.026] [PMID:  29339254] 
[16] 
Yin, Y.; Zhou, Y.; Sha, S.; Wu, X.; Wang, S-F.; Qiao, F.; Song, Z-C.; Zhu, H-L. Development of novel chromeno[4,3-c]pyrazol-4(2H)-one derivates containing piperazine as inhibitors of PI3Kα. Bioorg. Chem.,  2019, 92103238
[http://dx.doi.org/10.1016/j.bioorg.2019.103238] [PMID:  31499259] 
[17] 
García-López, V.; Palacios-Corella, M.; Clemente-León, M.; Coronado, E. Fe(II) spin crossover complexes of a derivative of 2,6-bis(pyrazol-1-yl)pyridine (1-bpp) functionalized with a carboxylic acid in the 3-pyridyl position. Polyhedron,  2019, 17015, 95-100.
[http://dx.doi.org/10.1016/j.poly.2019.05.029] 
[18] 
Angelova, V.T.; Valcheva, V.; Pencheva, T.; Voynikov, Y.; Vassilev, N.; Mihaylova, R.; Momekov, G.; Shivachev, B. Synthesis, antimycobacterial activity and docking study of 2-aroyl-[1]benzopyrano[4,3-c]pyrazol-4(1H)-one derivatives and related hydrazide-hydrazones. Bioorg. Med. Chem. Lett.,  2017, 27(13), 2996-3002.
[http://dx.doi.org/10.1016/j.bmcl.2017.05.011] [PMID:  28512022] 
[19] 
Epishina, M.A.; Kulikov, A.S.; Fershtat, L.L.; Ananyev, I.V.; Makhova, N.N. Synthesis of new pharmacologically oriented heterocyclic ensembles, [2-(1H-pyrazol-1-yl)thiazol-4-yl]furoxans. Mendeleev Commun.,  2019, 29, 288-291.
[http://dx.doi.org/10.1016/j.mencom.2019.05.015] 
[20] 
Abbas, H.S.; Abd El-Karim, S.S. Design, synthesis and anticervical cancer activity of new benzofuran-pyrazol-hydrazono- thiazolidin-4-one hybrids as potential EGFR inhibitors and apoptosis inducing agents. Bioorg. Chem.,  2019, 89103035
[http://dx.doi.org/10.1016/j.bioorg.2019.103035] [PMID:  31200286] 
[21] 
Ma, Q.; Zhang, G.; Li, J.; Zhang, Z.; Lu, H.; Liao, L.; Fan, G.; Nie, F. Pyrazol-triazole energetic hybrid with high thermal stability and decreased sensitivity: facile synthesis, characterization and promising performance. Chem. Eng. J.,  2020, 3791122331
[http://dx.doi.org/10.1016/j.cej.2019.122331] 
[22] 
Pechmann, H.V. Pechmann: Ueber. Ber. Dtsch. Chem. Ges.,  1894, 146, 9-12.
[23] 
Nair, D.; Pavashe, P.; Katiyar, S.; Namboothiri, I.N.N. Regioselective synthesis of pyrazole and pyridazine esters from chalcones and α-diazo-β-ketoesters. Tetrahedron Lett.,  2016, 57, 3146-3149.
[http://dx.doi.org/10.1016/j.tetlet.2016.06.020] 
[24] 
Knorr, L. Einwirkung substituirter Acetessigester auf Phenylhydrazin. Ber. Dtsch. Chem. Ges.,  1883, 16, 2597-2599.
[http://dx.doi.org/10.1002/cber.188301602194] 
[25] 
Andrews, J.M. BSAC Working Party on Susceptibility Testing. BSAC standardized disc susceptibility testing method (version 4). J. Antimicrob. Chemother.,  2005, 56(1), 60-76.
[http://dx.doi.org/10.1093/jac/dki124] [PMID:  15911553] 
[26] 
Sanjeeva Reddy, C.; Sanjeeva Rao, L.; Rajesh Kumar, G.; Nagaraj, A.; Agaraj, A.N. Synthesis of new 1,2,4-triazole[3,4-b][1,3,4] thiadiazoles bearing pyrazole as potent antimicrobial agents. Chem. Pharm. Bull. (Tokyo),  2010, 58(10), 1328-1331.
[http://dx.doi.org/10.1248/cpb.58.1328] [PMID:  20930399] 
[27] 
Syed, M.A.; Ramappa, A.K.; Alegaon, S. Synthesis and evaluation of antitubercular and anti-fungal activity of some novel 6-(4-substituted aryl)-2-(3, 5-dimethyl-1H-pyrazol-1-yl) imidazo [2,1-b][1, 3, 4] thiadiazole derivatives. Asian J. Pharm. Clin. Res.,  2013, 6, 47-51.

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DOI https://dx.doi.org/10.2174/1386207323666201019152206	Print ISSN 1386-2073
Publisher Name Bentham Science Publisher	Online ISSN 1875-5402

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Microwave-assisted Synthesis of Novel Pyrazole Derivatives and their Biological Evaluation as Anti-Bacterial Agents

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