One-pot Synthesis and Antimicrobial Activities of N-Substituted Pyrazoles from Nitro-olefins and Hydrazones
DOI:
https://doi.org/10.37285/ijpsn.2019.12.1.4Abstract
The aim of the current work was to synthesize a series of N-monosubstituted pyrazoles by the Michael addition of nitro olefins with N-mono substituted hydrazones. The synthesis was accomplished by taking various aldehydes in the reaction at room temperature for simple hydrazones and reflux for bulky hydrazones. The final products were characterized by detailed spectral analysis using Mass, NMR and IR spectroscopy. The final products were evaluated for their antibacterial and antifungal properties. All the compounds (1-10) showed significant antibacterial properties on both gram-positive and gram-negative bacteria. Interestingly, the selected microbes were found to be highly sensitive for compound 1, 3, 4, 8 and 9. The molecules are also antifungal in nature, they have significant inhibitory effect on the growth of Candida albicans and Aspergillus niger. These results indicate that the prepared pyrazoles can be the leads to the development of antimicrobial agents for deadly infections
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Keywords:
Cyclo-addition reaction, N-substituted hydrazones, N-substituted pyrazoles, antibacterial, antifungal
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Published
2019-01-31
How to Cite
1.
Thatavarthi P. One-pot Synthesis and Antimicrobial Activities of N-Substituted Pyrazoles from Nitro-olefins and Hydrazones. Scopus Indexed [Internet]. 2019 Jan. 31 [cited 2024 May 13];12(1):4381-7. Available from: https://www.ijpsnonline.com/index.php/ijpsn/article/view/279
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Research Articles
References
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Deng X and Mani NS. (2006). Reaction of N-monosubstituted hydrazones with nitroolefins: A novel regioselective pyrazole synthesis. Org Lett 8(16): 3505-3508.
Desai NC (2018). Synthesis and Antimicrobial Activity of Fluorine Containing Pyrazole-clubbed Dihydropyrimidinones. Int J Med Chem 80: 242-252.
Dominguez JN, Charris JE, Caparelli M and Riggione F (2002). Synthesis and antimalarial activity of substituted pyrazole derivatives. Arzne-Forsch 52(6): 482-8.
Gokhan Kelekci N, Koyunoglu S, Yabanoglu S, Yelekci K, Ozgen O, Ucar G and Yesilada, A (2009). New pyrazoline bearing 4(3H)-quinazolinone inhibitors of monoamine oxidase: Synthesis, biological evaluation, and structural determinants of MAO-A and MAO-B selectivity. Bioorg Med Chem 17(2): 675-689.
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Koca I, Ozgur A, Coskun KA, and Tutar Y (2013). Synthesis and anticancer activity of acyl thioureas bearing pyrazole moiety. Bioorgc Med Chem 21(13): 3859-3865.
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Sauzem PD, Sant Anna, Machado P, Duarte MF, Ferreira J, Mello CF and Rubin MA (2009). Effect of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles on chronic inflammatory pain model in rats. Eur J Pharmacol 616(1-3): 91-100.
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Sudheer Kumar Dokuparthi and Suresh Kandagatla (2017). Synthesis and in vitro antifungal activity of chalcone derivatives linked with 1, 2, 4 – triazole. Asia J pharm Anal Med Chem 5(1): 60-64.
Tanitame A, Oyamada Y, Ofuji K, Terauchi H, Kawasaki M, Wachi, M and Yamagishi JI (2005). Synthesis and antibacterial activity of a novel series of DNA gyrase inhibitors: 5-[(E)-2-arylvinyl]-pyrazoles. Bioorg Med Chem Lett 15(19): 4299-4303.
Tripathi AC, Upadhyay S, Paliwal S and Saraf SK (2018). Derivatives of 4,5-dihydro (1H) pyrazoles as possible MAO-A inhibitors in depression and anxiety disorders: synthesis, biological evaluation and molecular modeling studies. Med Chem Res 27(5): 1485-1503.
Vaghasiya S, Dodiya D, Trivedi A and Shah V (2008). Synthesis and biological screening of some novel pyrazolo thieno pyrimidin-8-ones via a Gewald reaction. Arkivoc 12(12), 1–8.
Yusuf M and Jain P (2014). Synthetic and biological studies of pyrazolines and related heterocyclic compounds. Arab J Chem 7(5): 553-596.
Amir M, Kumar H and Khan SA (2008). Synthesis and pharmacological evaluation of pyrazoline derivatives as new anti-inflammatory and analgesic agents. Bioorg Med Chem Lett 18(3): 918-922.
Argade ND, Kalrale BK and Gill CH (2008). Microwave assisted improved method for the synthesis of pyrazole containing 2,4,-disubstituted oxazole-5-one and their antimicrobial activity. E J Chem 5(1): 120-129.
Beyhan N, Kocyigit-Kaymakcioglu B, Gumru S and Aricioglu F (2017). Synthesis and anticonvulsant activity of some 2-pyrazolines derived from chalcones. Arab J Chem 10: S2073-S2081.
Chovatia PT, Akabari JD, Kachhadia PK, Zalavadia PD and Joshi HS (2006). Synthesis and selective antitubercular and antimicrobial inhibitory activity of 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives. J Serb Chem Soc 71(7): 713-720.
Datar PA and Jadhav SR (2015). Design and Synthesis of Pyrazole-3-one Derivatives as Hypoglycaemic Agents. Int J Med Chem 15: 1-10.
Deng X and Mani NS. (2006). Reaction of N-monosubstituted hydrazones with nitroolefins: A novel regioselective pyrazole synthesis. Org Lett 8(16): 3505-3508.
Desai NC (2018). Synthesis and Antimicrobial Activity of Fluorine Containing Pyrazole-clubbed Dihydropyrimidinones. Int J Med Chem 80: 242-252.
Dominguez JN, Charris JE, Caparelli M and Riggione F (2002). Synthesis and antimalarial activity of substituted pyrazole derivatives. Arzne-Forsch 52(6): 482-8.
Gokhan Kelekci N, Koyunoglu S, Yabanoglu S, Yelekci K, Ozgen O, Ucar G and Yesilada, A (2009). New pyrazoline bearing 4(3H)-quinazolinone inhibitors of monoamine oxidase: Synthesis, biological evaluation, and structural determinants of MAO-A and MAO-B selectivity. Bioorg Med Chem 17(2): 675-689.
Kaplanckl ZA, Ozdemir A, Turan Zitouni G, Altntop MD and Can OD (2010). New pyrazoline derivatives and their antidepressant activity. Eur J Med Chem 45(9): 4383-4387.
Kavanagh F (1972) Analytical Microbiology. Kavanagh F, Vol. 11: Academic Press, New York & London, 11.
Koca I, Ozgur A, Coskun KA, and Tutar Y (2013). Synthesis and anticancer activity of acyl thioureas bearing pyrazole moiety. Bioorgc Med Chem 21(13): 3859-3865.
Liu X, Huang X, Lin W, Wang D, Diao Y, Li H, and Ke D (2011). New aromatic substituted pyrazoles as selective inhibitors of human adipocyte fatty acid-binding protein. Bioorgc Med Chem Lett 21(10): 2949–2952.
Marzinzik AL, and Felder, ER (1997). Combinatorial libraries on rigid scaffolds: Solid phase synthesis of variably substituted pyrazoles and isoxazoles. Molecules 2(1): 17-30.
NSR and Kalluraya B (2007). Note A Novel synthesis of nitrofuran containing dipolar addition reaction, Ind J Chem 46: 375-378.
Pattan SR, Rabara PA, Pattan, JS, Bukitagar AA, Wakale VS and Musmade DS (2009). Synthesis and evaluation of some novel substituted 1,3,4-oxadiazole and pyrazole derivatives for antitubercular activity. Ind J Chem - Section B Org Med Chem 48(10): 1453-1456.
Ragavan RV, Vijayakumar V and Kumari NS (2010). Synthesis and antimicrobial activities of novel 1,5-diaryl pyrazoles. Eur J Med Chem 45(3): 1173-1180.
Rollas S and Kucukguzel SG (2007). Biological activities of hydrazone derivatives. Molecules 12(8): 1910-1939.
Sauzem PD, Sant Anna, Machado P, Duarte MF, Ferreira J, Mello CF and Rubin MA (2009). Effect of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles on chronic inflammatory pain model in rats. Eur J Pharmacol 616(1-3): 91-100.
Shih SR, Chu TY, Reddy GR, Tseng SN, Chen HL, Tang WF and Horng JT (2010). Pyrazole compound BPR1P0034 with potent and selective anti-influenza virus activity. J Biomed Sci 17: 13-18.
Singh P, Paul K and Holzer W (2006). Synthesis of pyrazole-based hybrid molecules: Search for potent multidrug resistance modulators. Bioorg Med Chem 14(14): 5061-5071.
Sudheer Kumar Dokuparthi and Suresh Kandagatla (2017). Synthesis and in vitro antifungal activity of chalcone derivatives linked with 1, 2, 4 – triazole. Asia J pharm Anal Med Chem 5(1): 60-64.
Tanitame A, Oyamada Y, Ofuji K, Terauchi H, Kawasaki M, Wachi, M and Yamagishi JI (2005). Synthesis and antibacterial activity of a novel series of DNA gyrase inhibitors: 5-[(E)-2-arylvinyl]-pyrazoles. Bioorg Med Chem Lett 15(19): 4299-4303.
Tripathi AC, Upadhyay S, Paliwal S and Saraf SK (2018). Derivatives of 4,5-dihydro (1H) pyrazoles as possible MAO-A inhibitors in depression and anxiety disorders: synthesis, biological evaluation and molecular modeling studies. Med Chem Res 27(5): 1485-1503.
Vaghasiya S, Dodiya D, Trivedi A and Shah V (2008). Synthesis and biological screening of some novel pyrazolo thieno pyrimidin-8-ones via a Gewald reaction. Arkivoc 12(12), 1–8.
Yusuf M and Jain P (2014). Synthetic and biological studies of pyrazolines and related heterocyclic compounds. Arab J Chem 7(5): 553-596.
