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Journal of Chemistry
Volume 2013 (2013), Article ID 543815, 9 pages
http://dx.doi.org/10.1155/2013/543815
Research Article

Synthesis, Antioxidant, Antimicrobial, Antimycobacterial, and Cytotoxic Activities of Azetidinone and Thiazolidinone Moieties Linked to Indole Nucleus

Department of Postgraduate Studies and Research in Chemistry, Gulbarga University, Gulbarga 585 106, India

Received 29 June 2012; Revised 20 August 2012; Accepted 3 October 2012

Academic Editor: Marco Radi

Copyright © 2013 A. R. Saundane and Prabhaker Walmik. 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. T. Finkel and N. J. Hoolbrook, “Oxidants, oxidative stress and the biology of ageing,” Nature, vol. 408, no. 6809, pp. 239–247, 2000.
  2. C. Soler-Rivas, J. C. Espin, and J. H. Wichers, “An easy and fast test to compare total free radical scavenger capacity of foodstuffs,” Phytochemical Analysis, vol. 11, pp. 330–338, 2000.
  3. S. P. Hussain, L. J. Hofseth, and C. C. Harris, “Radical causes of cancer,” Nature Reviews Cancer, vol. 3, no. 4, pp. 276–285, 2003. View at Scopus
  4. M. S. Cooke, M. D. Evans, M. Dizdaroglu, and J. Lunec, “Oxidative DNA damage: mechanisms, mutation, and disease,” FASEB Journal, vol. 17, no. 10, pp. 1195–1214, 2003. View at Publisher · View at Google Scholar · View at Scopus
  5. M. A. Babizhayev, A. I. Deyev, V. N. Yermakova, I. V. Brikman, and J. Bours, “Lipid peroxidation and cataracts: N-Acetylcarnosine as a therapeutic tool to manage age-related cataracts in human and in canine eyes,” Drugs in R and D, vol. 5, no. 3, pp. 125–139, 2004. View at Publisher · View at Google Scholar · View at Scopus
  6. I. Liu and M. Meydani, “Combined vitamin C and E supplementation retards early progression of arteriosclerosis in heart transplant patients,” Nutrition Reviews, vol. 60, no. 11, pp. 368–371, 2002. View at Publisher · View at Google Scholar
  7. S. Suzen, “Recent developments of melatonin related antioxidant compounds,” Combinatorial Chemistry and High Throughput Screening, vol. 9, no. 6, pp. 409–419, 2006. View at Publisher · View at Google Scholar · View at Scopus
  8. S. Suzen, Bozkaya, T. Coban, and D. Nebioglu, “Investigation of the in vitro antioxidant behaviour of some 2-phenylindole derivatives: discussion on possible antioxidant mechanisms and comparison with melatonin,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 21, no. 4, pp. 405–411, 2006. View at Publisher · View at Google Scholar
  9. D. L. Oliveria, S. M. Pugine, M. S. Ferreria, P. G. Links, E. J. Costa, and M. P. Demelo, “Influence of indole acetic acid on antioxidant levels and enzyme activities of glucose metabolism in rat liver,” Cell Biochemistry and Function, vol. 25, no. 2, pp. 195–201, 2007. View at Publisher · View at Google Scholar
  10. Y. Yamamoto and M. Kurazono, “A new class of anti-MRSA and anti-VRE agents: preparation and antibacterial activities of indole-containing compounds,” Bioorganic & Medicinal Chemistry Letters, vol. 17, no. 6, pp. 1626–1628, 2007. View at Publisher · View at Google Scholar
  11. S. Mahboobi, E. Eichhorn, A. Popp, A. Sellmer, S. Elz, and U. Mollmann, “3-Bromo-4-(1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione derivatives as new lead compounds for antibacterially active substances,” European Journal of Medicinal Chemistry, vol. 41, no. 2, pp. 176–191, 2006.
  12. C. K. Ryu, J. Y. Lee, R. E. Park, M. Y. Ma, and J. H. Nho, “Synthesis and antifungal activity of 1H-indole-4,7-diones,” Bioorganic & Medicinal Chemistry Letters, vol. 17, no. 1, pp. 127–131, 2007. View at Publisher · View at Google Scholar
  13. R. K. Tiwari, A. K. Verma, A. K. Chillar, et al., “Synthesis and antifungal activity of substituted-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indoles,” Bioorganic & Medicinal Chemistry, vol. 14, no. 8, pp. 2747–2752, 2006. View at Publisher · View at Google Scholar
  14. J. D. Williams, J. C. Drach, and L. B. Townsend, “Synthesis and antiviral activity of some 2-substituted 3-formyl-and 3-cyano-5,6-dichloroindole nucleosides,” Nucleosides, Nucleotides and Nucleic Acids, vol. 24, no. 10–12, pp. 1613–1626, 2005. View at Publisher · View at Google Scholar
  15. J. J. Chen, Y. Wei, J. D. Williums, J. C. Drach, and L. B. Townsend, “Design, synthesis, and antiviral evaluation of some polyhalogenated indole C-nucleosides,” Nucleosides, Nucleotides and Nucleic Acids, vol. 24, no. 10–12, pp. 1417–1437, 2005. View at Publisher · View at Google Scholar
  16. H. Chai, Y. Zhao, and C. P. Gong, “Synthesis and in vitro anti-hepatitis B virus activities of some ethyl 6-bromo-5-hydroxy-1H-indole-3-carboxylates,” Bioorganic & Medicinal Chemistry, vol. 14, no. 4, pp. 911–917, 2006. View at Publisher · View at Google Scholar
  17. A. Agarwal, K. Srivastav, S. K. Puri, and P. M. Chauhan, “Synthesis of substituted indole derivatives as a new class of antimalarial agents,” Bioorganic & Medicinal Chemistry Letters, vol. 15, no. 12, pp. 3133–3136, 2005. View at Publisher · View at Google Scholar
  18. J. L. Kgokong, P. P. Smith, and G. M. Matasabisa, “1,2,4-triazino-[5,6b]indole derivatives: effects of the trifluoromethyl group on in vitro antimalarial activity,” Bioorganic & Medicinal Chemistry, vol. 13, no. 8, pp. 2935–2942, 2005. View at Publisher · View at Google Scholar
  19. S. Suzen and B. Buyunkbingal, “Evaluation of anti-HIV activity of 5-(2-phenyl-3-indolal)-2-thiohydantoin,” IL Farmaco, vol. 53, no. 7, pp. 525–527, 1998. View at Publisher · View at Google Scholar
  20. G. De Martino, G. La Regina, R. Ragno et al., “Indolyl aryl sulphones as HIV-1 non-nucleoside reverse transcriptase inhibitors: synthesis, biological evaluation and binding mode studies of new derivatives at indole-2-carboxamide,” Antiviral Chemistry and Chemotherapy, vol. 17, no. 2, pp. 59–77, 2006. View at Scopus
  21. G. Dannhardt and W. Kiefer, “Cyclooxygenase inhibitors-Current status and future prospects,” European Journal of Medicinal Chemistry, vol. 36, pp. 109–126, 2001.
  22. D. W. Brown, P. R. Graupner, M. Sainsbury, and H. G. Shertzer, “New antioxidants incorporating indole and indoline chromophores,” Tetrahedron, vol. 47, no. 25, pp. 4383–4408, 1991. View at Publisher · View at Google Scholar · View at Scopus
  23. S. Suzen, Z. Alagoz, and M. O. Puskullu, “Antioxidant activities of indole and benzimidazole derivatives,” Fabad Journal of Pharmaceutical Sciences, vol. 25, no. 3, pp. 113–119, 2000. View at Scopus
  24. G. S. Singh and B. J. Mmolotsi, “Synthesis of 2-azetidinones from 2-diazo-1, 2-diarylethanones and N-(2-thienylidene)imines as possible antimicrobial agents,” Il Farmaco, vol. 60, no. 9, pp. 727–730, 2005. View at Publisher · View at Google Scholar · View at Scopus
  25. J. Anaya, D. S. Gero, H. Grande, J. Hermando, and N. M. Laso, “D-glucosamine propanedithioacetal, an efficient chiral auxiliary in β-Lactam chemistry1,” Bioorganic & Medicinal Chemistry, vol. 7, no. 5, pp. 837–850, 1999. View at Publisher · View at Google Scholar
  26. E. E. Kucukguzel, S. Oruc Rollas, F. Sahin, and A. Ozbek, “Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds,” European Journal of Medicinal Chemistry, vol. 37, no. 3, pp. 197–206, 2002. View at Publisher · View at Google Scholar
  27. G. Capan, N. Ulusoy, N. Ergenc, and M. Kiraz, “New 6-phenylimidazo[2,1-b]thiazole derivatives: synthesis and antifungal activity,” Monatshefte für Chemie, vol. 130, no. 11, pp. 1399–1407, 1999.
  28. A. R. Bhat and S. Shetty, “Synthesis of 4-thiazolidinones and azetidin-2-ones and their biological activities,” Indian Journal of Pharmaceutical Sciences, vol. 49, no. 5, pp. 194–197, 1987.
  29. N. S. Mahajan, S. R. Pattana, R. L. Jadhav, N. V. Pimpodhar, and A. M. Manikrao, “Synthesis of some thiazole compounds of biological interest containing mercapto group,” International Journal of Chemical Sciences, vol. 6, no. 2, pp. 800–806, 2008.
  30. K. M. Basavaraja, B. Somasekhar, and S. Appalaraju, “Synthesis and biological activity of some 2-[3-substituted-2-thione-1,3,4-thiazole-5-yl)aminobenzothiazoles,” Indian Journal of Heterocyclic Chemistry, vol. 18, pp. 69–72, 2008.
  31. A. A. Chowki, C. S. Magdum, P. L. Ladda, and S. K. Mohite, “Synthesis and antitubercular activity of 6-nitro-2-[4-formyl-3-(substituted phenyl)pyrazol-1-yl]benzothiazoles,” International Journal of Chemical Sciences, vol. 6, no. 3, pp. 1600–1605, 2008.
  32. K. P. Bhusari, P. B. khedekar, S. N. Umathe, R. H. Bahekar, and R. R. A. Raghu, “Synthesis of 8-bromo-9-substituted-1,3-benzothiazolo[5,1-b]1,3,4-triazoles and their anthelmintic activity,” Indian Journal of Heterocyclic Chemistry, vol. 9, pp. 275–278, 2000.
  33. R. Basavaraj, M. Suresh, and S. S. Sangapure, “Synthesis and pharmacological activities of some 2-arylamino/arylidene hydrazino-4-(5’-chloro-3’-methylbenzofuran-2’-yl)thiazoles,” Indian Journal of Heterocyclic Chemistry, vol. 15, pp. 153–156, 2005.
  34. N. Lozach, “Forty years of Heterocyclic Sulphur Chemistry in Sulphur Reports,” vol. 10, no. 7, 1990.
  35. A. K. Zafer, T. Z. Gulhan, O. Ahmet, and R. Gilbert, “New triazole and triazolothiadiazine derivatives as possible antimicrobial agents,” European Journal of Medicinal Chemistry, vol. 43, no. 1, pp. 155–159, 2008. View at Publisher · View at Google Scholar
  36. T. P. T. Cushnie and A. J. Lamb, “Antimicrobial activity of flavonoids,” International Journal of Antimicrobial Agents, vol. 26, no. 5, pp. 343–356, 2005. View at Publisher · View at Google Scholar · View at Scopus
  37. Q. Meng, H. Luo, Y. Chen, Y. Wang, and Q. Yao, “Synthesis of novel [1,2]-diamines with antituberculosis activity,” Bioorganic & Medicinal Chemistry Letters, vol. 19, no. 18, pp. 5372–5375, 2006. View at Publisher · View at Google Scholar
  38. A. R. Saundane, M. Yarlakatti, W. Prabhaker, and V. Katkar, “Synthesis, antioxidant and antimicrobial evaluation of thiazolidinone, azetidinone encompassing indolylthienopyrimidines,” Journal of Chemical Sciences, vol. 124, no. 2, pp. 469–481, 2012. View at Publisher · View at Google Scholar
  39. A. R. Saundane, V. Katkar, A. V. Vaijinath, and W. Prabhaker, “Synthesis, antimicrobial and antioxidant activities of some new indole derivatives containing pyridopyrimidine and pyrazolopyridine moieties,” Medicinal Chemistry Research. In press. View at Publisher · View at Google Scholar
  40. A. R. Saundane, W. Prabhaker, V. Katkar, and M. Yarlakatti, “Synthesis, antimicrobial and antioxidant activities of pyrimido[5,4-e]thiazolo[3,2-a]pyrimidines linked to indole nucleus,” Heterocyclic Letters, vol. 2, no. 1, pp. 53–70, 2012.
  41. A. R. Saundane, V. Katkar, M. Yarlakatti, A. V. Vaijinath, and W. Prabhaker, “Synthesis and biological activity of some 5-substituted 2-phenyl-3-(6-aryl-3-cyano-2-substituted pyridin-4-yl)indole and their derivatives,” Indian Journal of Heterocyclic chemistry, vol. 20, pp. 321–324, 2011.
  42. R. M. Dodson and L. C. King, “The reaction of ketones with halogens and thiourea,” Journal of the American Chemical Society, vol. 67, no. 12, pp. 2242–2243, 1945. View at Scopus
  43. S. P. Hiremath, J. S. Biradar, and M. G. Purohit, “A new route to indolo[3,2-b]isoquinolines,” Indian Journal of Chemistry B, vol. 21, pp. 249–253, 1982.
  44. I. Calis, M. Hosny, T. Khalifa, and S. Nishibe, “Secoiridoids from Fraxinus angustifolia,” Phytochemistry, vol. 33, no. 6, pp. 1453–1456, 1993. View at Scopus
  45. T. Hatano, H. Kangawa, T. Yasuhara, and T. Okuda, “Two new flavonoids and other constituents in licorice root: their relative astringency and radical scavenging effects,” Chemical & Pharmaceutical Bulletin, vol. 36, no. 6, pp. 2090–2097, 1988. View at Publisher · View at Google Scholar
  46. M. Oyaizu, “Antioxidative activity of browning substances on glucosamine,” Japan Nutrition, vol. 44, no. 6, pp. 307–315, 1986. View at Publisher · View at Google Scholar
  47. T. C. P. Dinis, V. M. C. Maderia, and L. M. Almeida, “Action of phenolic derivatives (acetoaminophen, salycilate, and 5-aminosalycilate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers,” Archives of Biochemistry and Biophysics, vol. 315, pp. 161–169, 1994.
  48. Indian Pharmacopeia, Government of India, New Delhi Appendix IV, 3rd edition, 1985.
  49. C. S. L. Maria, M. V. N. de Souza, C. Alessandra, et al., “Evaluation of anti-tubercular activity of nicotinic and isoniazid analogues,” ARKIVOK, vol. 15, pp. 181–191, 2007.
  50. A. Dolly and J. B. Griffiths, Cell and Tissue Culture for Medical Research, John Wiley & Sons.