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Journal of Chemistry
Volume 2013, Article ID 741953, 9 pages
http://dx.doi.org/10.1155/2013/741953
Research Article

Ultrasonication-Induced Synthesis and Antimicrobial Evaluation of Some Multifluorinated Pyrazolone Derivatives

1P. G. Department of Chemistry and Research Centre, Padmashri Vikhe Patil College, Pravaranagar, Ahmednagar 413713, India
2Department of Chemistry, Radhabai Kale Mahila Mahavidyalaya, Ahmednagar 414001, India

Received 6 June 2012; Revised 6 August 2012; Accepted 28 August 2012

Academic Editor: Qing Li

Copyright © 2013 Anil Gadhave et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. N. Woodford, “Novel agents for the treatment of resistant Gram-positive infections,” Expert Opinion on Investigational Drugs, vol. 12, no. 2, pp. 117–137, 2003. View at Publisher · View at Google Scholar · View at Scopus
  2. L. Kuznetsova, M. I. Ungureau, and A. Pepe, “Trifluoromethyl- and difluoromethyl-β-lactams as useful building blocks for the synthesis of fluorinated amino acids, dipeptides, and fluoro-taxoids,” Journal of Fluorine Chemistry, vol. 125, no. 4, pp. 415–500, 2004. View at Publisher · View at Google Scholar
  3. M. A. Al-Haiza, S. A. El-Assiery, and G. H. Sayed, “Synthesis and potential antimicrobial activity of some new compounds containing the pyrazol-3-one moiety,” Acta Pharmaceutica, vol. 51, no. 4, pp. 251–261, 2001. View at Google Scholar · View at Scopus
  4. F. Moreau, N. Desroy, J. M. Genevard et al., “Discovery of new Gram-negative antivirulence drugs: structure and properties of novel E. coli WaaC inhibitors,” Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 14, pp. 4022–4026, 2008. View at Publisher · View at Google Scholar · View at Scopus
  5. R. N. Mahajan, F. H. Havaldar, and P. S. Fernandes, “Syntheses and biological activity of heterocycles derived from 3-methoxy-1-phenyl-1H-pyrazole-5-carboxylate,” Journal of the Indian Chemical Society, vol. 68, no. 4, pp. 245–246, 1991. View at Google Scholar · View at Scopus
  6. D. Castagnolo, F. Manetti, M. Radi et al., “Synthesis, biological evaluation, and SAR study of novel pyrazole analogues as inhibitors of Mycobacterium tuberculosis: part 2. Synthesis of rigid pyrazolones,” Bioorganic and Medicinal Chemistry, vol. 17, no. 15, pp. 5716–5721, 2009. View at Publisher · View at Google Scholar · View at Scopus
  7. M. Radi, V. Bernardo, B. Bechi, D. Castagnolo, M. Pagano, and M. Botta, “Microwave-assisted organocatalytic multicomponent Knoevenagel/hetero Diels-Alder reaction for the synthesis of 2,3-dihydropyran[2,3-c]pyrazoles,” Tetrahedron Letters, vol. 50, no. 47, pp. 6572–6575, 2009. View at Publisher · View at Google Scholar · View at Scopus
  8. E. A. M. Badawey and I. M. El-Ashmawey, “Nonsteroidal antiinflammatory agents—part 1: antiinflammatory, analgesic and antipyretic activity of some new 1-(pyrimidin-2-yl)-3-pyrazolin-5-ones and 2-(pyrimidin-2-yl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-ones,” European Journal of Medicinal Chemistry, vol. 33, no. 5, pp. 349–361, 1998. View at Publisher · View at Google Scholar
  9. A. Tantawy, H. Eisa, A. Ismail, and M. E. Alexandria, “Synthesis of 1-(substituted) 4-arylhydrazono-3-methyl-2-pyrazolin-5-ones as potential antiinflammatory agents,” Journal of Pharmaceutical Sciences, vol. 2, p. 133, 1988. View at Google Scholar
  10. F. A. Pasha, M. Muddassar, M. M. Neaz, and S. J. Cho, “Pharmacophore and docking-based combined in-silico study of KDR inhibitors,” Journal of Molecular Graphics and Modelling, vol. 28, no. 1, pp. 54–61, 2009. View at Publisher · View at Google Scholar · View at Scopus
  11. C. E. Rosiere and M. I. Grossman, “An analog of histamine that stimulates gastric acid secretion without other actions of histamine,” Science, vol. 113, no. 2945, p. 651, 1951. View at Google Scholar · View at Scopus
  12. D. M. Bailey, P. E. Hansen, A. G. Hlavac et al., “3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants,” Journal of Medicinal Chemistry, vol. 28, no. 2, pp. 256–260, 1985. View at Google Scholar · View at Scopus
  13. P. M. S. Chauhan, S. Singh, and R. K. Chatterjee, “Antifilarial profile of substituted pyrazoles: a new class of antifilarial agents,” Indian Journal of Chemistry B, vol. 32, pp. 858–861, 1993. View at Google Scholar
  14. X. Zhang, Y. Kluger, Y. Nakayama et al., “Gene expression in mature neutrophils: early responses to inflammatory stimuli,” Journal of Leukocyte Biology, vol. 75, no. 2, pp. 358–372, 2004. View at Publisher · View at Google Scholar · View at Scopus
  15. M. T. Quinn and K. A. Gauss, “Structure and regulation of the neutrophil respiratory burst oxidase: comparison with nonphagocyte oxidases,” Journal of Leukocyte Biology, vol. 76, pp. 760–781, 2004. View at Publisher · View at Google Scholar
  16. S. J. Weiss, “Tissue destruction by neutrophils,” The New England Journal of Medicine, vol. 320, pp. 365–376, 1989. View at Publisher · View at Google Scholar
  17. M. Himly, B. Jahn-Schmid, K. Pittertschatscher et al., “Ig E-mediated immediate-type hypersensitivity to the pyrazolone drug propyphenazone,” Journal of Allergy and Clinical Immunology, vol. 111, no. 4, pp. 882–888, 2003. View at Publisher · View at Google Scholar · View at Scopus
  18. T. Watanabe, S. Yuki, M. Egawa, and H. Nishi, “Protective effects of MCI-186 on cerebral ischemia: possible involvement of free radical scavenging and antioxidant actions,” Journal of Pharmacology and Experimental Therapeutics, vol. 268, pp. 1597–1604, 1994. View at Google Scholar
  19. H. Kawai, H. Nakai, M. Suga, S. Yuki, T. Watanabe, and K. I. Saito, “Effects of a novel free radical scavenger, MCI-186, on ischemic brain damage in the rat distal middle cerebral artery occlusion model,” Journal of Pharmacology and Experimental Therapeutics, vol. 281, no. 2, pp. 921–927, 1997. View at Google Scholar · View at Scopus
  20. T. W. Wu, L. H. Zeng, J. Wu, and K. P. Fung, “Myocardial protection of MCI-186 in rabbit ischemia-reperfusion,” Life Sciences, vol. 71, no. 19, pp. 2249–2255, 2002. View at Publisher · View at Google Scholar · View at Scopus
  21. R. Aggarwal, V. Kumar, P. Tyagi, and S. P. Singh, “Synthesis and antibacterial activity of some new 1-heteroaryl-5-amino-3H/ methyl-4-phenylpyrazoles,” Bioorganic and Medicinal Chemistry, vol. 14, no. 6, pp. 1785–1791, 2006. View at Publisher · View at Google Scholar · View at Scopus
  22. V. Kumar, R. Aggarwal, P. Tyagi, and S. P. Singh, “Synthesis and antibacterial activity of some new 1-heteroaryl-5-amino-4-phenyl-3-trifluoromethylpyrazoles,” European Journal of Medicinal Chemistry, vol. 40, no. 9, pp. 922–927, 2005. View at Publisher · View at Google Scholar
  23. J. L. Kane, B. H. Hirth, B. Liang, B. B. Gourlie, S. Nahill, and G. Barsomian, “Ureas of 5-aminopyrazole and 2-aminothiazole inhibit growth of gram-positive bacteria,” Bioorganic and Medicinal Chemistry Letters, vol. 13, no. 24, pp. 4463–4466, 2003. View at Publisher · View at Google Scholar · View at Scopus
  24. P. P. Deohate, J. P. Deohate, and B. N. Berad, “Synthesis of some novel 1,2,4-dithiazolidines and their antibacterial and antifungal activity,” Asian Journal of Chemistry, vol. 16, no. 1, pp. 255–260, 2004. View at Google Scholar · View at Scopus
  25. O. Prakash, R. Kumar, and V. Prakash, “Synthesis and antifungal activity of some new 3-hydroxy-2-(1-phenyl-3-aryl-4-pyrazolyl) chromones,” European Journal of Medicinal Chemistry, vol. 43, pp. 435–440, 2008. View at Publisher · View at Google Scholar
  26. K. L. Kees, J. J. Fitzgerald, K. E. Steiner et al., “New potent antihyperglycemic agents in db/db mice: synthesis and structure-activity relationship studies of (4-substituted benzyl)(trifluoromethyl)pyrazoles and -pyrazolones,” Journal of Medicinal Chemistry, vol. 39, no. 20, pp. 3920–3928, 1996. View at Publisher · View at Google Scholar · View at Scopus
  27. G. Meazza, F. Bettarini, P. La Porta et al., “Synthesis and herbicidal activity of novel heterocyclic protoporphyrinogen oxidase inhibitors,” Pest Management Science, vol. 60, no. 12, pp. 1178–1188, 2004. View at Publisher · View at Google Scholar · View at Scopus
  28. T. W. Waldrep, J. R. Beck, M. P. Lynch, and F. L. Wright, “Synthesis and herbicidal activity of 1-aryl-5-halo- and 1-aryl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamides,” Journal of Agricultural and Food Chemistry, vol. 38, no. 2, pp. 541–544, 1990. View at Google Scholar · View at Scopus
  29. D. J. Wustrow, T. Capiris, R. Rubin et al., “Pyrazolo[1,5-a]pyrimidine CRF-1 receptor antagonists,” Bioorganic and Medicinal Chemistry Letters, vol. 8, no. 16, pp. 2067–2070, 1998. View at Publisher · View at Google Scholar · View at Scopus
  30. A. G. Habeeb, P. N. Praveen Rao, and E. E. Knaus, “Design and synthesis of celecoxib and rofecoxib analogues as selective cyclooxygenase-2 (COX-2) inhibitors: replacement of sulfonamide and methylsulfonyl pharmacophores by an azido bioisostere,” Journal of Medicinal Chemistry, vol. 44, no. 18, pp. 3039–3042, 2001. View at Publisher · View at Google Scholar · View at Scopus
  31. A. M. Martel, A. Graul, X. Rabasseda, and R. Castañer, “Sildenafil,” Drugs of the Future, vol. 22, no. 2, pp. 138–143, 1997. View at Google Scholar · View at Scopus
  32. A. S. Bhat, J. L. Whetstone, and R. W. Brueggemeier, “Novel synthetic routes suitable for constructing benzopyrone combinatorial libraries,” Tetrahedron Letters, vol. 40, no. 13, pp. 2469–2472, 1999. View at Publisher · View at Google Scholar · View at Scopus
  33. B. Bauvois, M. L. Puiffe, J. B. Bongui, S. Paillat, C. Monneret, and D. Dauzonne, “Synthesis and biological evaluation of novel flavone-8-acetic acid derivatives as reversible inhibitors of aminopeptidase N/CD13,” Journal of Medicinal Chemistry, vol. 46, no. 18, pp. 3900–3913, 2003. View at Publisher · View at Google Scholar · View at Scopus
  34. H. P. Kim, K. H. Son, H. W. Chang, and S. S. Kang, “Anti-inflammatory plant flavonoids and cellular action mechanisms,” Journal of Pharmacological Sciences, vol. 96, no. 3, pp. 229–245, 2004. View at Publisher · View at Google Scholar
  35. E. Middleton, C. Kandaswami, and T. C. Theoharides, “The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer,” Pharmacological Reviews, vol. 52, no. 4, pp. 673–751, 2000. View at Google Scholar · View at Scopus
  36. C. J. Bennett, S. T. Caldwell, D. B. McPhail, P. C. Morrice, G. G. Duthie, and R. C. Hartley, “Potential therapeutic antioxidants that combine the radical scavenging ability of myricetin and the lipophilic chain of vitamin E to effectively inhibit microsomal lipid peroxidation,” Bioorganic and Medicinal Chemistry, vol. 12, no. 9, pp. 2079–2098, 2004. View at Publisher · View at Google Scholar · View at Scopus
  37. V. Krishnamachari, L. H. Levine, C. Zhou, and P. W. Pare, “In vitro flavon-3-ol oxidation mediated by a B ring hydroxylation pattern,” Chemical Research in Toxicology, vol. 17, no. 6, pp. 795–804, 2004. View at Publisher · View at Google Scholar
  38. E. Knoevenagel, “Condensation von Malonsure mit aromatischen Aldehyden durch Ammoniak und Amine,” Berichte der deutschen chemischen Gesellschaft, vol. 31, no. 3, pp. 2596–2619, 1898. View at Publisher · View at Google Scholar
  39. E. Castelli, G. Cascio, and E. Manghisi, WO, 9807698, 1988.
  40. A. J. Kesel and W. Oberthur, WO, 9820013, 1998.
  41. A. Gaplovsky, M. Gaplovsky, S. Toma, and J. L. Luche, “Ultrasound effects on the photopinacolization of benzophenone,” Journal of Organic Chemistry, vol. 65, no. 25, pp. 8444–8447, 2000. View at Publisher · View at Google Scholar · View at Scopus
  42. R. Rajgopal, D. V. Jarikote, and K. V. Srinivasan, “Ultrasound prompted Suzuki cross-coupling reactions in ionic liquids at ambient conditions,” Chemical Communications, no. 6, pp. 616–617, 2002. View at Publisher · View at Google Scholar
  43. B. A. Song, G. P. Zhang, S. Yang, D. Y. Hu, and L. H. Jin, “Synthesis of N-(4-bromo-2-trifluoromethylphenyl)-1-(2-fluorophenyl)-O,O-dialkyl-α-aminophosphonates under ultrasonic irradiation,” UltraChem, vol. 13, p. 1544, 2001. View at Google Scholar
  44. S. S. Shindalkar, B. R. Madje, and M. S. Shingare, “A simple procedure for the preparation of acylals from 4-oxo-(4H)-1- benzopyran-3-carboxaldehyde using envirocat EPZ10R catalyst under ultrasonic irradiation,” Indian Journal of Heterocyclic Chemistry, vol. 15, no. 1, pp. 81–82, 2005. View at Google Scholar · View at Scopus
  45. B. K. Karale and A. G. Gadhave, “Synthesis and antibacterial activity of some spiroisoxazolines,” Indian Journal of Heterocyclic Chemistry, vol. 19, no. 4, pp. 389–392, 2010. View at Google Scholar · View at Scopus
  46. R. B. Gaikar, A. G. Gadhave, and B. K. Karale, “Synthesis of some biologically active pyrazolones,” Indian Journal of Heterocyclic Chemistry, vol. 19, no. 4, pp. 325–328, 2010. View at Google Scholar · View at Scopus
  47. A. V. Gadakh, C. Pandit, S. S. Rindhe, and B. K. Karale, “Synthesis and antimicrobial activity of novel fluorine containing 4-(substituted-2-hydroxybenzoyl)-1H-pyrazoles and pyrazolyl benzo[d]oxazoles,” Bioorganic and Medicinal Chemistry Letters, vol. 20, no. 18, pp. 5572–5576, 2010. View at Publisher · View at Google Scholar · View at Scopus
  48. Clinical and Laboratory Standards Institute (CLSI), “Performance standards for antimicrobial susceptibility testing: 15th informational supplement,” CLSI Document M100-S15, Wayne, Pa, USA, 2005. View at Google Scholar
  49. B. S. Furniss, A. J. Hannaford, P. W. G. Smith, and A. R. Patchel, Vogels Text Book of Practical Organic Chemistry, Pearson Education, 5th edition, 2007.