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Journal of Chemistry
Volume 2013 (2013), Article ID 148412, 9 pages
http://dx.doi.org/10.1155/2013/148412
Research Article

Synthesis and Antimicrobial and Antioxidant Activities of Some New 5-(2-Methyl-1H-indol-3-yl)-1,3,4-oxadiazol-2-amine Derivatives

1Department of Post-Graduate Studies and Research in Chemistry, Gulbarga University, Gulbarga 585 106, India
2Shri Prabhu Arts, Science & J. M. Bohra Commerce Degree College, Shorapur, Karnataka 585 224, India

Received 31 May 2013; Revised 18 August 2013; Accepted 9 September 2013

Academic Editor: Jose Alberto Pereira

Copyright © 2013 Anand R. Saundane 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. S. Harper, B. Pacini, S. Avolio et al., “Development and preliminary optimization of indole-N-acetamide inhibitors of hepatitis C virus NS5B polymerase,” Journal of Medicinal Chemistry, vol. 48, no. 5, pp. 1314–1317, 2005. View at Publisher · View at Google Scholar · View at Scopus
  2. G. N. Anilkumar, C. A. Lesburg, O. Selyutin et al., “I. Novel HCV NS5B polymerase inhibitors: Discovery of indole 2-carboxylic acids with C3-heterocycles,” Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 18, pp. 5336–5341, 2011. View at Publisher · View at Google Scholar · View at Scopus
  3. G. N. Anilkumar, C. A. Lesburg, O. Selyutin et al., “II Novel HVC NS5B polymerase inhibitors: discovovery of indole C2 acyl sulfuonamides,” Bioorganic & Medicinal Chemistry Letters, vol. 22, pp. 713–717, 2012. View at Google Scholar
  4. J. F. Dropinski, T. Akiyama, M. Einstein et al., “Synthesis and biological activities of novel aryl indole-2-carboxylic acid analogs as PPARγ partial agonists,” Bioorganic and Medicinal Chemistry Letters, vol. 15, no. 22, pp. 5035–5038, 2005. View at Publisher · View at Google Scholar · View at Scopus
  5. R. Akue-Gedu, E. Debiton, Y. Ferandin et al., “Synthesis and biological activities of aminopyrimidyl-indoles structurally related to meridianins,” Bioorganic and Medicinal Chemistry, vol. 17, no. 13, pp. 4420–4424, 2009. View at Publisher · View at Google Scholar · View at Scopus
  6. M.-J. R. P. Queiroz, A. S. Abreu, M. S. D. Carvalho, P. M. T. Ferreira, N. Nazareth, and M. São-José Nascimento, “Synthesis of new heteroaryl and heteroannulated indoles from dehydrophenylalanines: antitumor evaluation,” Bioorganic and Medicinal Chemistry, vol. 16, no. 10, pp. 5584–5589, 2008. View at Publisher · View at Google Scholar · View at Scopus
  7. C.-K. Ryu, J. H. Yoon, A. L. Song, H. A. Im, J. Y. Kim, and A. Kim, “Synthesis and antifungal evaluation of pyrido[1,2-a]indole-1,4-diones and benzo[f]pyrido[1,2-a]indole-6,11-diones,” Bioorganic and Medicinal Chemistry Letters, vol. 22, no. 1, pp. 497–499, 2012. View at Publisher · View at Google Scholar · View at Scopus
  8. D. S. Mehta, K. H. Sikotra, and V. H. Shah, “Synthesis and biological screening of some new novel indole derivatives,” Indian Journal of Chemistry B, vol. 44, no. 12, pp. 2594–2597, 2005. View at Google Scholar · View at Scopus
  9. A. Scribner, J. A. Moore III, G. Ouvry et al., “Synthesis and biological activity of anticoccidial agents: 2,3-diarylindoles,” Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 5, pp. 1517–1521, 2009. View at Publisher · View at Google Scholar · View at Scopus
  10. A. Zarghi, S. A. Tabatabai, M. Faizi et al., “Synthesis and anticonvulsant activity of new 2-substituted-5-(2- benzyloxyphenyl)-1,3,4-oxadiazoles,” Bioorganic and Medicinal Chemistry Letters, vol. 15, no. 7, pp. 1863–1865, 2005. View at Publisher · View at Google Scholar · View at Scopus
  11. A. N. Krasovskii, A. K. Bulgakov, A. P. Andrushko et al., “Antimicrobial and tuberculostatic activity of 5-aryl(hetaryl)-1,3,4-oxadiazole-2-thiones and their derivatives,” Pharmaceutical Chemistry Journal, vol. 34, no. 3, pp. 115–117, 2000. View at Google Scholar · View at Scopus
  12. S. V. Bhandari, K. G. Bothara, M. K. Raut, A. A. Patil, A. P. Sarkate, and V. J. Mokale, “Design, synthesis and evaluation of antiinflammatory, analgesic and ulcerogenicity studies of novel s-substituted phenacyl-1,3,4-oxadiazole-2-thiol and schiff bases of diclofenac acid as nonulcerogenic derivatives,” Bioorganic and Medicinal Chemistry, vol. 16, no. 4, pp. 1822–1831, 2008. View at Publisher · View at Google Scholar · View at Scopus
  13. B. S. Sudha, S. Shashikanth, S. A. Khanum, and S. N. Sriharsha, “Synthesis and pharmacological screening of 5-(4-aroyl)-aryloxy methyl-2-thio-1,3,4-oxadiazole,” Indian Journal of Pharmaceutical Sciences, vol. 65, no. 5, pp. 465–470, 2003. View at Google Scholar · View at Scopus
  14. K. M. Lokanatha Rai and N. Linganna, “Synthesis and evaluation of antimitotic activity of alkylated 2-amino- 1,3,4-oxadiazole derivatives,” Farmaco, vol. 55, no. 5, pp. 389–392, 2000. View at Publisher · View at Google Scholar · View at Scopus
  15. S. Saxena, M. Verma, A. K. Saxena, and K. Shanker, “1,3,4-oxadiazole thiones as inflammation inhibitors,” Indian Journal of Pharmaceutical Sciences, vol. 54, no. 1, pp. 1–3, 1992. View at Google Scholar · View at Scopus
  16. M. Zareef, R. Iqbal, N. A. Al-Masoudi, J. H. Zaidi, M. Arfan, and S. A. Shahzad, “Synthesis, anti-HIV, and antifungal activity of new benzensulfonamides bearing the 2,5-disubstituted-1,3,4-oxadiazole moiety,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 182, no. 2, pp. 281–298, 2007. View at Publisher · View at Google Scholar · View at Scopus
  17. E. Meyer, A. C. Joussef, and L. D. B. P. De Souza, “Synthesis of new 1,2,4- and 1,3,4-oxadiazole derivatives as potential nonpeptide angiotensin II receptor antagonists,” Synthetic Communications, vol. 36, no. 6, pp. 729–741, 2006. View at Publisher · View at Google Scholar · View at Scopus
  18. K. M. Khan, S. A. Shahzadi, M. Ranil et al., “Structure-activity relationship of tyrosinase inhibitory combinatorial library of 2,5- disubstituted-1,3,4-oxadiazole,” Letters in Organic Chemistry, pp. 3286–3288, 2006. View at Google Scholar
  19. M. Shaban, A. E. Nasar, and S. M. EL-Badary, “Synthesis of some 1,3,4-oxadiazole and bis 1,3,4-oxadiazole that possess nematicidal insecticidal and herbicidal activity,” Journal of Islamic Academy of Sciences, vol. 4, no. 3, pp. 184–191, 1991. View at Google Scholar
  20. A.-R. A. H. Farghaly, “Synthesis, reactions and antimicrobial activity of some new indolyl-1,3,4-oxadiazole, triazole and pyrazole derivatives,” Journal of the Chinese Chemical Society, vol. 51, no. 1, pp. 147–156, 2004. View at Google Scholar · View at Scopus
  21. B. Narayana, B. V. Ashalatha, K. K. Vijaya Raj, and B. K. Sarojini, “Synthesis and studies on antimicrobial, antiinflammatory and antiproliferative activities of heterocycles derived from 4-/5-/6-/7-nitro/ 5fluoro/chloro/bromoindole-2-carbohydrazides,” Indian Journal of Chemistry B, vol. 48, no. 12, pp. 1794–1805, 2009. View at Google Scholar · View at Scopus
  22. M. Bhalla, V. K. Srivastava, T. N. Bhalla, and K. Shanker, “Anti-inflammatory and analgesic activity of indolyl quinazolones and their congeners,” Arzneimittel-Forschung/Drug Research, vol. 43, no. 5, pp. 595–600, 1993. View at Google Scholar · View at Scopus
  23. P. B. R. Kumar, S. Subramaniyan, K. Yamini, and R. Suthakaran, “Synthesis of some novel 1-H pyrazole derivatives and their antibacterial activity studies,” Rasayan Journal of Chemistry, vol. 4, no. 2, pp. 400–404, 2011. View at Google Scholar · View at Scopus
  24. 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. View at Google Scholar
  25. Indian Pharmacopeia, Appendix 4, Government of India, New Delhi, India, 3rd edition, 1985.
  26. T. Hatano, H. Kagawa, T. Yasuhara, and T. Okuda, “Two new flavonoids and other constituents in licorice root: their relative astringency and radical scavenging effects,” Chemical and Pharmaceutical Bulletin, vol. 36, no. 6, pp. 2090–2097, 1988. View at Google Scholar · View at Scopus
  27. M. Strlič, T. Radovič, J. Kolar, and B. Pihlar, “Anti- and prooxidative properties of gallic acid in fenton-type systems,” Journal of Agricultural and Food Chemistry, vol. 50, no. 22, pp. 6313–6317, 2002. View at Publisher · View at Google Scholar · View at Scopus
  28. M. Oyaizu, “Studies on products of the browning reaction. Antioxidative activities of browning reactionproducts prepared fromglucosamine,” Japanese Journal of Nutrition, vol. 44, no. 6, pp. 307–315, 1986. View at Google Scholar
  29. T. C. P. Dinis, V. M. C. Madeira, and L. M. Almeida, “Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers,” Archives of Biochemistry and Biophysics, vol. 315, no. 1, pp. 161–169, 1994. View at Publisher · View at Google Scholar · View at Scopus