SYNTHESIS AND IN-VITRO ANTIMICROBIAL STUDIES OF SOME NEW PYRAZOLONES

Authors

  • Poonam Gupta School of Studies in Chem istry, Jiwaji Un iversity, Gwalior
  • Jitendra Kumar Gupta School of Studies in Chem istry, Jiwaji Un iversity, Gwalior
  • Shivani Bansal School of Studies in Chem istry, Jiwaji Un iversity, Gwalior
  • A. K. Halve School of Studies in Chem istry, Jiwaji Un iversity, Gwalior

Keywords:

Pyrazolones, Thiosemicarbazides, Antimicrobial activity, Disc diffusion technique

Abstract

In the present scenario antibacterial agents are the greatest contribution of chemotherapy. They have great importance in the developing countries where infectious diseases predominate. Pyrazolone derivatives are an important class of heterocyclic compounds that occur in many drugs and synthetic products. It has a particular value due to their broad spectrum of biological activities and their utility as synthetic tools in the design of various bioactive molecules. It is also exhibited analgesic, antipyretic and anti-inflammatory activity. In the present study, a series of 3-methyl-N-(substituted phenyl)-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothioamide (3a-g) were synthesized by the reaction of thiosemicarbazides (1) and ethylacetoacetate (2) in DMF. The synthesized compounds were characterized on the basis of IR, 1H-NMR, 13C-NMR and elemental analysis.

All synthesized compounds were screened for antimicrobial activities using disc diffusion technique against four bacterial pathogens viz Staphylococcus aureus, Escherichia coli, Bacillus anthracis and Pseudomonas aeruginosa & two fungal pathogens namely Candida albicanes, Aspergillus niger. Chloramphenicol and Fluconazole were used as standard drug respectively. The compounds exhibit moderate activity.

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References

Mariappan G, Saha BP, Sutharson L, Singh A, Garg S, Pandey L, et al. The diverse pharmacological importance of pyrazolone derivatives. J Pharm Res 2010;3:2856-9.

Micha L. Hypersensitivity to pyrazolones. Thorax 2000;55:S72–S74.

Halen PK, Yadav MR, Murumkar P, Giridhar R. Prodrug designing of NSAIDs. Mini Rev Med Chem 2009;9:124-39.

Himly M, Jahn-Schmid B, Pittertschatscher K, Bohle B, Grubmayr K, Ferreira F, et al. Ig E-mediated immediate-type hypersensitivity to the pyrazolone drug propyhenazone. J Allergy Clin Immunol 2003;111:882-8.

Al-Haiza MA, El-Assiery SA, Sayed GH. Synthesis and potential antimicrobial activity of some new compounds containing the pyrazol-3-one moiety. Acta Pharm 2001;51:251-61.

Castagnolo D, Manetti F, Radi M, Bechi B, Pagano M, De Logu A, et al. Synthesis, biological evaluation, and SAR study of novel pyrazole analogues as inhibitors of Mycobacterium tuberculosis: Part 2. Synthesis of rigid pyrazolones. Bioorg Med Chem 2009;17:5716-21.

Radi M, Bernardo V, Bechi B, Castagnolo D. Microwave-assisted organocatalytic multicomponent Knoevenagel/hetero Diels–Alder reaction for the synthesis of 2,3-dihydropyran[2,3-c]pyrazoles. Tetrahedron Lett 2009;50:6572-5.

Moreau F, Desroy N, Genevard JM, Vongsouthi V, Gerusz V. Discovery of new Gram-negative antivirulence drugs: structure and properties of novel E. coli WaaC inhibitors. Bioorg Med Chem Lett 2008;18:4022-6.

Sauzem PD, Machado P, Rubin MA, Sant’Anna GS, Faber HB. Design and microwave-assisted synthesis of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles: novel agents with analgesic and anti-inflammatory properties. Eur J Med Chem 2008;43:1237-47.

Pasha FA, Muddassar M, Neaz MM, Cho SJ. Pharmacophore and docking-based combined in-silico study of KDR inhibitors. J Mol Graph Model 2009;28:54-61.

Rosiere CE, Grossman MI. An analog of histamine that stimulates gastric acid secretion without other actions of histamine. Sci 1951;113:651-3.

Bailey DM, Hansen PE, Hlavac AG, Baizman ER, Pearl J. 3, 4-Diphenyl-1H-Pyrazole-1-propanamine antidepressants. J Med Chem 1985;28:256-60.

Chauhan PMS, Singh S, Chatterjee RK. Antifilarial profile of substituted pyrazoles: a new class of antifilarial agents. Indian J Chem Sect B 1993;32:858-61.

Peruncheralathan S, Khan TA, Ila H, Junjappa H. Regioselective synthesis of 1-aryl-3,4-substituted/annulated-5-(methylthio)pyrazoles and 1-aryl-3-(methylthio)-4,5-substituted/annulated pyrazoles. J Org Chem 2005;70:10030-5.

Tong A, Akama Y, Tanaka S. Reversed-phase high-performance liquid chromatography of aluminium (III) and indium (III) with 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone. J Chromatogr 1989;478:408-14.

Ziarati A, Safaei-Ghomi A, Rohani S. Sonochemically synthesis of pyrazolones using reusable catalyst CuI nanoparticles that was prepared by sonication. Ultrason Sonochem 2013;20:1069–75.

Pettinari C, Marchetti F, Cingolani A, Leonesi D, Troyanov S, Drozdov A. New co-ordination compounds derived from barium(II) and the anionic 4-tert-butylacetyl-3-methyl-1-phenylpyrazol-5-onate ligand (Q–). J Chem Soc Dalton Trans 1999;1555-62.

Ihesinachi KA, Augustus UB, Chukwu UJ. Extraction of Chromium (Vi) with 4-Adipoyl and 4-Sebacoyl Derivatives of Bis (1-Phenyl-3-Methylpyrazolone-5) in acid medium and the effect of butanol. Nat Sci 2011;9:147-53.

Samelson H, Lempicki A. Fluorescence and lifetimes of Eu chelates. J Chem Phys 1963;39:110-2.

Shestopalov AM, Emelyanova YM, Shestopalov AA, Rodinovskaya LA, Niazimbetova ZI, Evans DH. Cross of substituted 6-amino-spiro-4-(N-R-piperidine-4')-2H,4H-pyrano[2,3-condensation of derivatives of cyanoacetic acid and carbonyl compounds. Part 1. One-stage synthesis c]pyrazole-5-carbonitriles. Tetrahedron 2003;59:7491-6.

Otto HH. Synthesis of Some 4H-Pyrano[2.3-c]pyrazoles. Arch Pharm 1974:307:444-7.

Abdou S, Fahmy SM, Sadek KU, Elnagdi MH. Darstellung einiger 4H-Pyrano[2,3-c]pyrazolderivate. Heterocycl 1981;16:2177-80.

Gokcen E, Serdar U, Maria-Teresa N, Labeaga L, Francisco L. Synthesis, biological evalution, and docking studies of novel heterocyclic diaryl compounds as selective COX-2 inhibitors. Bioorg Med Chem 2010;18:6367–76.

Kuppusamy S, Gnanamani S, Nagarajan PS, Seeralan M, Paramasivan TP, Melani R. Synthesis and antiviral activity of 4,40-(arylmethylene)bis(1H-pyrazol-5-ols) against peste des petits ruminant virus (PPRV). Bioorg Med Chem Lett 2009;19:4501–3.

Anonymous, British Pharmacopoeia, Voll II, HMS Publication Center, London; 1988. p. A205,

Ochei J, Kolhatkar A. Medicinal Laboratory Science-Theory and Pracitces. Tata McGrow-Hill Publishing Co. Ltd. New Delhi; 2000. p. 808-18.

Barry AL. The Antimicrobial Susceptibility Test: Principal and Practices, lllu lea and Febiger, Philadephia, Pa, USA;1976. p. 180-95.

Isloor AM, Kalluraya B, Pai KS. Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives. Eur J Med Chem 2010;45:825-30.

Chandrakantha B, Shetty P, Nambiyar V, Isloor N, Isloor AM. Synthesis, characterization and biological activity of some new 1,3,4-oxadiazole bearing 2-flouro-4-methoxy phenyl moiety. Eur J Med Chem 2010;45:1206-10.

Rai US, Isloor AM, Shetty P, Vijesh AM, Prabhu N, Isloor S, et al. Novel chromeno [2,3-b]-pyrimidine derivatives as potential anti-microbial agents. Eur J Med Chem 2010;45:2695-9.

Vijesh AM, Isloor AM, Prabhu V, Ahmad S, Malladi S. Synthesis of some new pyrazolone derivatives as potent antimicrobial agents. Eur J Med Chem 2010;45:5460-4.

Khan R, Uddin MI, Alam MS, Hossain MM, Islam MR. Synthesis and preliminary evaluation of brominated 5-methyl-2,4-dihydropyrazol-3-one and its derivatives as cytotoxic agents. Bangladesh J Pharmacol 2008;3:27-35.

Published

06-01-2015

How to Cite

Gupta, P., J. K. Gupta, S. Bansal, and A. K. Halve. “SYNTHESIS AND IN-VITRO ANTIMICROBIAL STUDIES OF SOME NEW PYRAZOLONES”. International Journal of Current Pharmaceutical Research, vol. 7, no. 1, Jan. 2015, pp. 25-29, https://mail.innovareacademics.in/journals/index.php/ijcpr/article/view/4712.

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