Table of Contents
Organic Chemistry International
Volume 2013, Article ID 976032, 8 pages
http://dx.doi.org/10.1155/2013/976032
Research Article

Green Chemical Synthesis and Analgesic Activity of Fluorinated Thiazolidinone, Pyrazolidinone, and Dioxanedione Derivatives

1Department of Chemistry, Faculty of Engineering and Technology, Mody Institute of Technology and Science, Lakshmangarh, Sikar, Rajasthan 332311, India
2Goenka College of Pharmacy, Goenka Institute of Education and Research (GIER), Lakshmangarh, Sikar, Rajasthan 332311, India

Received 7 April 2013; Revised 28 June 2013; Accepted 28 June 2013

Academic Editor: William Setzer

Copyright © 2013 Harshita Sachdeva 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. Ş. G. Küçükgüzel, S. Rollas, H. Erdeniz, M. Kiraz, A. Cevdet Ekinci, and A. Vidin, “Synthesis, characterization and pharmacological properties of some 4-arylhydrazono-2-pyrazoline-5-one derivatives obtained from heterocyclic amines,” European Journal of Medicinal Chemistry, vol. 35, no. 7-8, pp. 761–771, 2000. View at Publisher · View at Google Scholar · View at Scopus
  2. S. A. F. Rostom, I. M. El-Ashmawy, H. A. Abd El Razik, M. H. Badr, and H. M. A. Ashour, “Design and synthesis of some thiazolyl and thiadiazolyl derivatives of antipyrine as potential non-acidic anti-inflammatory, analgesic and antimicrobial agents,” Bioorganic and Medicinal Chemistry, vol. 17, no. 2, pp. 882–895, 2009. View at Publisher · View at Google Scholar · View at Scopus
  3. S. Khode, V. Maddi, P. Aragade et al., “Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents,” European Journal of Medicinal Chemistry, vol. 44, no. 4, pp. 1682–1688, 2009. View at Publisher · View at Google Scholar · View at Scopus
  4. M. Abdel-Aziz, G. E. A. Abuo-Rahma, and A. A. Hassan, “Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities,” European Journal of Medicinal Chemistry, vol. 44, no. 9, pp. 3480–3487, 2009. View at Publisher · View at Google Scholar · View at Scopus
  5. Z. S. Quan, R. L. Li, and Y. Z. Ling, “Study of the relationship between structure and anticonvulsant activities of 5-substituted-1-butry-3-pyrazolidinones and their synthesis,” Acta Pharmaceutica Sinica, vol. 27, no. 9, pp. 711–716, 1992. View at Google Scholar · View at Scopus
  6. N. Das, A. Verma, P. K. Shrivastava, and S. K. Shrivastava, “Synthesis and biological evaluation of some new aryl pyrazol-3-one derivatives as potential hypoglycemic agents,” Indian Journal of Chemistry B, vol. 47, no. 10, pp. 1555–1558, 2008. View at Google Scholar · View at Scopus
  7. G. A. Idrees, O. M. Aly, G. E. A. A. Abuo-Rahma, and M. F. Radwan, “Design, synthesis and hypolipidemic activity of novel 2-(naphthalen-2-yloxy)propionic acid derivatives as desmethyl fibrate analogs,” European Journal of Medicinal Chemistry, vol. 44, no. 10, pp. 3973–3980, 2009. View at Publisher · View at Google Scholar · View at Scopus
  8. G. Ouyang, Z. Chen, X. Cai et al., “Synthesis and antiviral activity of novel pyrazole derivatives containing oxime esters group,” Bioorganic and Medicinal Chemistry, vol. 16, no. 22, pp. 9699–9707, 2008. View at Publisher · View at Google Scholar · View at Scopus
  9. 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
  10. K. B. Umesha, K. M. L. Rai, and M. A. Harish Nayaka, “Antioxidant and antimicrobial activity of 5-methyl-2-(5-methyl-1,3-diphenyl-1H-pyrazole-4-carbonyl)-2,4-dihydro-pyrazol-3-one,” International Journal of Biomedical Science, vol. 5, no. 4, pp. 359–368, 2009. View at Google Scholar · View at Scopus
  11. R. Tripathy, A. Ghose, J. Singh et al., “1,2,3-Thiadiazole substituted pyrazolones as potent KDR/VEGFR-2 kinase inhibitors,” Bioorganic and Medicinal Chemistry Letters, vol. 17, no. 6, pp. 1793–1798, 2007. View at Publisher · View at Google Scholar · View at Scopus
  12. H. Park, K. Lee, S. Park et al., “Identification of antitumor activity of pyrazole oxime ethers,” Bioorganic and Medicinal Chemistry Letters, vol. 15, no. 13, pp. 3307–3312, 2005. View at Publisher · View at Google Scholar · View at Scopus
  13. R. Murugan, S. Anbazhagan, and S. S. Narayanan, “Synthesis and in vivo antidiabetic activity of novel dispiropyrrolidines through [3 + 2] cycloaddition reactions with thiazolidinedione and rhodanine derivatives,” European Journal of Medicinal Chemistry, vol. 44, no. 8, pp. 3272–3279, 2009. View at Publisher · View at Google Scholar · View at Scopus
  14. S. Chandrappa, C. V. Kavitha, M. S. Shahabuddin et al., “Synthesis of 2-(5-((5-(4-chlorophenyl)furan-2-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid derivatives and evaluation of their cytotoxicity and induction of apoptosis in human leukemia cells,” Bioorganic and Medicinal Chemistry, vol. 17, no. 6, pp. 2576–2584, 2009. View at Publisher · View at Google Scholar · View at Scopus
  15. E. W. Brooke, S. G. Davies, A. W. Mulvaney et al., “Synthesis and in vitro evaluation of novel small molecule inhibitors of bacterial arylamine N-acetyltransferases (NATs),” Bioorganic and Medicinal Chemistry Letters, vol. 13, no. 15, pp. 2527–2530, 2003. View at Publisher · View at Google Scholar · View at Scopus
  16. S. Ozkirimli, F. Kazan, and Y. Tunali, “Synthesis, antibacterial and antifungal activities of 3-(1,2,4-triazol-3-yl)-4-thiazolidinones,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 24, no. 2, pp. 447–452, 2009. View at Publisher · View at Google Scholar · View at Scopus
  17. S. Chandrappa, S. B. Benaka Prasad, K. Vinaya, C. S. Ananda Kumar, N. R. Thimmegowda, and K. S. Rangappa, “Synthesis and in vitro antiproliferative activity against human cancer cell lines of novel 5-(4-methyl-benzylidene)-thiazolidine-2,4-diones,” Investigational New Drugs, vol. 26, no. 5, pp. 437–444, 2008. View at Publisher · View at Google Scholar · View at Scopus
  18. A. Verma and S. K. Saraf, “4-Thiazolidinone—a biologically active scaffold,” European Journal of Medicinal Chemistry, vol. 43, no. 5, pp. 897–905, 2008. View at Publisher · View at Google Scholar · View at Scopus
  19. D. Davidson and S. A. Bernhard, “The structure of Meldrum's supposed β-lactonic acid,” Journal of the American Chemical Society, vol. 70, no. 10, pp. 3426–3428, 1948. View at Google Scholar · View at Scopus
  20. K. Byun, Y. Mo, and J. Gao, “New insight on the origin of the unusual acidity of Meldrum's acid from αβ-initio and combined QM/MM simulation study,” Journal of the American Chemical Society, vol. 123, no. 17, pp. 3974–3979, 2001. View at Publisher · View at Google Scholar · View at Scopus
  21. B. Chen, “Meldrum's acid in organic synthesis,” Heterocycles, vol. 32, no. 3, pp. 529–597, 1991. View at Google Scholar · View at Scopus
  22. L. F. Tietze and U. Beifuss, “The knoevenagel reaction,” in Comprehensive Organic Synthesis, vol. 2, pp. 341–394, 1991. View at Google Scholar
  23. B. Pita, E. Sotelo, M. Suárez et al., “Pyridazine derivatives. Part 21: synthesis and structural study of novel 4-aryl-2,5-dioxo-8-phenylpyrido[2,3-d]pyridazines,” Tetrahedron, vol. 56, no. 16, pp. 2473–2479, 2000. View at Publisher · View at Google Scholar · View at Scopus
  24. F. C. Brown, C. K. Bradsher, and S. M. Bond, “Some 5-substituted rhodanines,” Industrial & Engineering Chemistry, vol. 45, pp. 1030–1032, 1953. View at Google Scholar
  25. K. Ramkumar, V. N. Yarovenko, A. S. Nikitina et al., “Design, synthesis and structure-activity studies of rhodanine derivatives as HIV-1 integrase inhibitors,” Molecules, vol. 15, no. 6, pp. 3958–3992, 2010. View at Publisher · View at Google Scholar · View at Scopus
  26. J. Iwao and K. J. Tomino, “Synthesis of pyrazolo [3, 4-b] pyridine by knovengel condensation,” Pharmaceutical Society of Japan, vol. 76, pp. 748–755, 1956. View at Google Scholar
  27. B. A. Alekseenko, T. E. Gorizdra, and S. N. Baranov, “Synthesis and structure of noncondensed bicyclic thiazolidino-4-one derivatives,” Khimiya Geterotsiklicheskikh Soedinenii, vol. 5, pp. 230–231, 1969. View at Google Scholar
  28. G. G. Allan, D. Maclean, and G. T. Newbold, “Condensation products of rhodanine, and keto-acids,” Journal of the Chemical Society, pp. 5132–5153, 1952. View at Google Scholar · View at Scopus
  29. F. C. Brown, C. K. Bradsher, S. G. McCallum, and M. Potter, “Rhodanine derivatives of ketones,” Journal of Organic Chemistry, vol. 15, no. 1, pp. 174–176, 1950. View at Google Scholar · View at Scopus
  30. M. M. Chowdhry, D. M. P. Mingos, A. J. P. White, and D. J. Williams, “Syntheses and characterization of 5-substituted hydantoins and thiazolines - Implications for crystal engineering of hydrogen bonded assemblies. Crystal structures t of 5-(2-pyridylmethylene)-hydantoin, 5-(2-pyridylmethylene)-2-thiohydantoin, 5-(2-pyridylmethylene)thiazolidine-2,4-dione, 5-(2-pyridylmethylene)rhodanine and 5-(2-pyridylmethylene)pseudothiohydantoin,” Journal of the Chemical Society, Perkin Transactions 1, vol. 1, no. 20, pp. 3495–3504, 2000. View at Publisher · View at Google Scholar · View at Scopus
  31. R. V. Hangarge, D. V. Jarikote, and M. S. Shingare, “Knoevenagel condensation reactions in an ionic liquid,” Green Chemistry, vol. 4, no. 3, pp. 266–268, 2002. View at Publisher · View at Google Scholar · View at Scopus
  32. S. S. Shindalkar, B. R. Madje, and M. S. Shingare, “Microwave induced, solvent-free Knoevenagel condensation of 4-oxo-(4H)-1-benzopyran-3-carbaldehyde with Meldrum's acid using alumina support,” Indian Journal of Chemistry B, vol. 45, no. 11, pp. 2571–2573, 2006. View at Google Scholar · View at Scopus
  33. S. Santosh, B. R. Shindalkar, R. V. Madje, P. T. Hangarge, M. K. D. Patil, and M. S. Shingare, “Borate zirconia mediated Knoevenagel condensation reaction in water,” Journal of the Korean Chemical Society, vol. 49, pp. 377–380, 2005. View at Google Scholar
  34. S. S. Shindalkar, B. R. Madje, and M. S. Shingare, “Ultrasonically accelerated Knoevenagel condensation reaction at room temperature in distilled water,” Indian Journal of Chemistry B, vol. 44, no. 7, pp. 1519–1521, 2005. View at Google Scholar · View at Scopus
  35. N. B. Darvatkar, A. R. Deorukhkar, S. V. Bhilare, and M. M. Salunkhe, “Ionic liquid-mediated knoevenagel condensation of Meldrum's acid and aldehydes,” Synthetic Communications, vol. 36, no. 20, pp. 3043–3051, 2006. View at Publisher · View at Google Scholar · View at Scopus
  36. J. M. Khurana and K. Vij, “Nickel nanoparticles catalyzed chemoselective Knoevenagel condensation of Meldrum's acid and tandem enol lactonizations via cascade cyclization sequence,” Tetrahedron Letters, vol. 52, no. 28, pp. 3666–3669, 2011. View at Publisher · View at Google Scholar · View at Scopus
  37. S. Ghosh, J. Das, and S. Chattopadhyay, “A novel light induced Knoevenagel condensation of Meldrum's acid with aromatic aldehydes in aqueous ethanol,” Tetrahedron Letters, vol. 52, no. 22, pp. 2869–2872, 2011. View at Publisher · View at Google Scholar · View at Scopus
  38. A. M. Dumas, A. Seed, A. K. Zorzitto, and E. Fillion, “Triphenylphosphine mediated Knoevenagel condensation of Meldrum's acid with aromatic aldehydes,” Tetrahedron Letters, vol. 48, pp. 7072–7276, 2007. View at Google Scholar
  39. K. Gong, Z. He, Y. Xu, D. Fang, and Z. Liu, “Green synthesis of 5-benzylidene rhodanine derivatives catalyzed by 1-butyl-3-methyl imidazolium hydroxide in water,” Monatshefte fur Chemie, vol. 139, no. 8, pp. 913–915, 2008. View at Publisher · View at Google Scholar · View at Scopus
  40. K. F. Shelke, S. B. Sapkal, B. R. Madja, B. B. Shingate, and M. S. Shingare, “Ionic liquid promoted an efficient synthesis of 5-arylidene-2, 4-thiazolidinedione,” Bulletin of the Catalysis Society of India, vol. 8, pp. 30–34, 2009. View at Google Scholar
  41. J. Zhou, Y. Song, F. Zhu, and Y. Zhu, “Facile synthesis of 5-benzylidene rhodamine derivatives under microwave irradiation,” Synthetic Communications, vol. 36, no. 22, pp. 3297–3303, 2006. View at Publisher · View at Google Scholar · View at Scopus
  42. K. Bourahla, A. Derdour, M. Rahmouni, F. Carreaux, and J. P. Bazureau, “A practical access to novel 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones via sulfur/nitrogen displacement under solvent-free microwave irradiation,” Tetrahedron Letters, vol. 48, no. 33, pp. 5785–5789, 2007. View at Publisher · View at Google Scholar · View at Scopus
  43. S. Patil, S. D. Jadhav, and U. P. Patil, “Natural acid catalyzed synthesis of schiff base under solvent-free condition: as a green approach,” Journal of Applied Sciences Research, vol. 4, no. 2, pp. 1074–1078, 2012. View at Google Scholar
  44. H. L. Yale, “The trifluoromethyl group in medicinal chemistry,” Journal of Medicinal and Pharmaceutical Chemistry, vol. 1, no. 2, pp. 121–133, 1959. View at Google Scholar · View at Scopus
  45. P. C. Appelbaum and P. A. Hunter, “The fluoroquinolone antibacterials: past, present and future perspectives,” International Journal of Antimicrobial Agents, vol. 16, no. 1, pp. 5–15, 2000. View at Publisher · View at Google Scholar · View at Scopus
  46. F. M. D. Ismail, G. B. D. Michael, and J. Michael, “Modulation of drug pharmacokinetics and pharmacodynamics by fluorine substitution,” Chemistry today, vol. 27, no. 3, pp. 18–21, 2009. View at Google Scholar
  47. H. Sachdeva, D. Dwivedi, K. Arya, S. Khaturia, and R. Saroj, “Anti-inflammatory activity, and QSAR study of some Schiff bases derived from 5-mercapto-3-(4-pyridyl)-4H-1,2,4-triazol-4-yl-thiosemicarbazide,” Medicinal Chemistry Research, 2013. View at Publisher · View at Google Scholar
  48. A. Dandia, H. Sachdeva, and R. Singh, “Improved synthesis of 3-spiro indolines in dry media under microwave irradiation,” Synthetic Communications, vol. 31, no. 12, pp. 1879–1892, 2001. View at Publisher · View at Google Scholar · View at Scopus
  49. H. Sachdeva, D. Dwivedi, and S. Khaturia, “Aqua mediated facile synthesis of 2-(5/7-fluorinated-2-oxoindolin-3-ylidene)-N- (4-substituted phenyl) hydrazine carbothioamides,” Research Journal of Pharmaceutical, Biological and Chemical Sciences, vol. 2, no. 2, pp. 213–219, 2011. View at Google Scholar · View at Scopus
  50. H. Sachdeva and D. Dwivedi, “Lithium-acetate-mediated biginelli one-pot multicomponent synthesis under solvent-free conditions and cytotoxic activity against the human lung Cancer Cell line A549 and Breast Cancer cell line MCF7,” The Scientific World Journal, vol. 2012, Article ID 109432, 9 pages, 2012. View at Publisher · View at Google Scholar