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The Scientific World Journal
Volume 2014, Article ID 581737, 10 pages
http://dx.doi.org/10.1155/2014/581737
Research Article

A Mini Library of Novel Triazolothiadiazepinylindole Analogues: Synthesis, Antioxidant and Antimicrobial Evaluations

1Central Research Lab, Department of Chemistry, Gulbarga University, Gulbarga, Karnataka State 585 106, India
2Smt. V.G. Degree College for Women, Gulbarga, Karnataka State 585 102, India
3Organic Chemistry Section, Chemical Science and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR), Thiruvanthapuram-695 019, Kerala, India

Received 23 August 2013; Accepted 4 December 2013; Published 20 February 2014

Academic Editors: L. Previtera and M. Wujec

Copyright © 2014 Jaiprakash Sharanappa Biradar 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. V. Lennon, S. J. Martin, and T. G. Cotter, “Dose-dependent induction of apoptosis in human tumour cell lines by widely diverging stimuli,” Cell Proliferation, vol. 24, no. 2, pp. 203–214, 1991. View at Google Scholar · View at Scopus
  2. H. Shirinzadeh, B. Eren, H. Gurer-Orhan, S. Suzen, and S. Özden, “Novel indole-based analogs of melatonin: synthesis and in vitro antioxidant activity studies,” Molecules, vol. 15, no. 4, pp. 2187–2202, 2010. View at Publisher · View at Google Scholar · View at Scopus
  3. M. L. Circu and T. Y. Aw, “Reactive oxygen species, cellular redox systems, and apoptosis,” Free Radical Biology and Medicine, vol. 48, no. 6, pp. 749–762, 2010. View at Publisher · View at Google Scholar · View at Scopus
  4. Y. Hangun-Balkir and M. L. McKenney, “Determination of antioxidant activities of berries and resveratrol,” Green Chemistry Letters and Reviews, vol. 5, no. 2, pp. 147–153, 2012. View at Publisher · View at Google Scholar · View at Scopus
  5. F. Regoli and G. Principato, “Glutathione, glutathione-dependent and antioxidant enzymes in mussel, Mytilus galloprovincialis exposed to metals under field and laboratory conditions: implications for the use of biochemical biomarkers,” Aquatic Toxicology, vol. 31, no. 2, pp. 143–164, 1995. View at Publisher · View at Google Scholar · View at Scopus
  6. N. Topalca, E. Yegin, and I. Celik, “Influence of indole-3-butyric acid on antioxidant defense systems in various tissues of rats at subacute and subchronic exposure,” Food and Chemical Toxicology, vol. 47, no. 10, pp. 2441–2444, 2009. View at Publisher · View at Google Scholar · View at Scopus
  7. H. E. Poulsen, H. Prieme, and S. Loft, “Role of oxidative DNA damage in cancer initiation and promotion,” European Journal of Cancer Prevention, vol. 7, no. 1, pp. 9–16, 1998. View at Google Scholar · View at Scopus
  8. M. Liu, X. Q. Li, C. Weber, C. Y. Lee, J. Brown, and R. H. Liu, “Antioxidant and antiproliferative activities of raspberries,” Journal of Agricultural and Food Chemistry, vol. 50, no. 10, pp. 2926–2930, 2002. View at Publisher · View at Google Scholar · View at Scopus
  9. B. Halliwell, “Role of free radicals in the neurodegenerative diseases: therapeutic implications for antioxidant treatment,” Drugs & Aging, vol. 18, no. 9, pp. 685–716, 2001. View at Google Scholar · View at Scopus
  10. K. Sudha, A. Rao, S. Rao, and A. Rao, “Free radical toxicity and antioxidants in Parkinson's disease,” Neurology India, vol. 51, no. 1, pp. 60–62, 2003. View at Google Scholar · View at Scopus
  11. G. S. Yossi, M. Eldad, and O. Daniel, “Oxidative stress induced-neurodegenerative diseases: the need for antioxidants that penetrate the blood brain barrier,” Neuropharmacology, vol. 40, no. 8, pp. 959–975, 2001. View at Publisher · View at Google Scholar · View at Scopus
  12. K. Asplund, “Antioxidant vitamins in the prevention of cardiovascular disease: a systematic review,” Journal of Internal Medicine, vol. 251, no. 5, pp. 372–392, 2002. View at Publisher · View at Google Scholar · View at Scopus
  13. K. N. Prasad, W. C. Cole, and B. Kumar, “Multiple antioxidants in the prevention and treatment of Parkinson's disease,” Journal of the American College of Nutrition, vol. 18, no. 5, pp. 413–423, 1999. View at Google Scholar · View at Scopus
  14. C. Li-Hsun, C. Chia-Mao, B. S. Deepak, and S. Chung-Ming, “Divergent synthesis of unsymmetrical annulated biheterocyclic compound libraries: benzimidazole linked indolo-benzodiazepines/quinoxaline,” ACS Combinatorial Science, vol. 13, no. 4, pp. 391–398, 2011. View at Publisher · View at Google Scholar · View at Scopus
  15. M. García-Valverde and T. Torroba, “Special issue: sulfur-nitrogen heterocycles,” Molecules, vol. 10, no. 2, pp. 318–320, 2005. View at Google Scholar · View at Scopus
  16. T. Karabasanagouda, A. V. Adhikari, and N. S. Shetty, “Synthesis and antimicrobial activities of some novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines carrying thioalkyl and sulphonyl phenoxy moieties,” European Journal of Medicinal Chemistry, vol. 42, no. 4, pp. 521–529, 2007. View at Publisher · View at Google Scholar · View at Scopus
  17. M. D. Mullican, M. W. Wilson, D. T. Connor, C. R. Kostlan, D. J. Schrier, and R. D. Dyer, “Design of 5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-thiadiazoles, -1,3,4-oxadiazoles, and -1,2,4-triazoles as orally-active, nonulcerogenic antiinflammatory agents,” Journal of Medicinal Chemistry, vol. 36, no. 8, pp. 1090–1099, 1993. View at Google Scholar · View at Scopus
  18. T. Wen-Jie and H. Yong-Zhou, “Simple and efficient one-pot synthesis of 2,4-diaryl-1,2,3-triazoles,” Synthetic Communications, vol. 36, no. 17, pp. 2461–2468, 2006. View at Publisher · View at Google Scholar · View at Scopus
  19. Y. A. Al-Soud, N. A. Al-Masoudi, and A. R. Ferwanah, “Synthesis and properties of new substituted 1,2,4-triazoles: potential antitumor agents,” Bioorganic & Medicinal Chemistry, vol. 11, no. 8, pp. 1701–1708, 2003. View at Publisher · View at Google Scholar · View at Scopus
  20. B. S. Holla, B. Veerendra, M. K. Shivananda, and B. Poojary, “Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles,” European Journal of Medicinal Chemistry, vol. 38, no. 7-8, pp. 759–767, 2003. View at Publisher · View at Google Scholar · View at Scopus
  21. S. F. Barbuceanu, G. L. Almajan, I. Saramet, C. Draghici, R. Socoteanu, and F. Barbuceanu, “New S-alkylated 1,2,4-triazoles incorporating diphenyl sulfone moieties with potential antibacterial activity,” Journal of the Serbian Chemical Society, vol. 74, no. 10, pp. 1041–1049, 2009. View at Publisher · View at Google Scholar · View at Scopus
  22. A.-R. Farghaly, E. De Clercq, and H. El-Kashef, “Synthesis and antiviral activity of novel [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles, [1,2,4]triazolo[3,4-b][1,3,4] thiadiazines and [1,2,4]triazolo[3,4-b] [1,3,4] thiadiazepines,” Arkivoc, vol. 2006, no. 10, pp. 137–151, 2006. View at Publisher · View at Google Scholar · View at Scopus
  23. M. Kidwai, P. Sapra, P. Misra, R. Saxena, and M. Singh, “Microwave assisted solid support synthesis of novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazepines as potent antimicrobial agents,” Bioorganic & Medicinal Chemistry, vol. 9, no. 2, pp. 217–220, 2001. View at Publisher · View at Google Scholar · View at Scopus
  24. E. R. Abbey, L. N. Zakharov, and S.-Y. Liu, “Boron in disguise: the parent fused BN indole,” Journal of the American Chemical Society, vol. 133, no. 30, pp. 11508–11511, 2011. View at Publisher · View at Google Scholar · View at Scopus
  25. F.-R. Alexandre, A. Amador, S. Bot et al., “Synthesis and biological evaluation of aryl-phospho-indole as novel HIV-1 non-nucleoside reverse transcriptase inhibitors,” Journal of Medicinal Chemistry, vol. 54, no. 1, pp. 392–395, 2011. View at Publisher · View at Google Scholar · View at Scopus
  26. A. J. Kochanowska-Karamyan and M. T. Hamann, “Marine indole alkaloids: potential new drug leads for the control of depression and anxiety,” Chemical Reviews, vol. 110, no. 8, pp. 4489–4497, 2010. View at Publisher · View at Google Scholar · View at Scopus
  27. B. S. Sasidhar and J. S. Biradar, “Synthesis of some bisindolyl analogs for in vitro cytotoxic and DNA cleavage studies,” Medicinal Chemistry Research, vol. 22, no. 7, pp. 3518–3526, 2013. View at Publisher · View at Google Scholar
  28. J. S. Biradar and B. S. Sasidhar, “Solvent-free, microwave assisted Knoevenagel condensation of novel 2,5-disubstituted indole analogues and their biological evaluation,” European Journal of Medicinal Chemistry, vol. 46, no. 12, pp. 6112–6118, 2011. View at Publisher · View at Google Scholar · View at Scopus
  29. J. S. Biradar, B. S. Sasidhar, and R. Parveen, “Synthesis, antioxidant and DNA cleavage activities of novel indole derivatives,” European Journal of Medicinal Chemistry, vol. 45, no. 9, pp. 4074–4078, 2010. View at Publisher · View at Google Scholar · View at Scopus
  30. J. S. Biradar, R. Parveen, B. S. Sasidhar, and S. M. Praveen, “Synthesis of new indolyl benzodiazepines and their DNA cleavage and antimicrobial activities,” Indian Journal of Heterocyclic Chemistry, vol. 20, pp. 181–182, 2010. View at Google Scholar
  31. J. S. Biradar, Studies in the indole field [Ph.D. thesis], Gulbarga University, Gulbarga, India, 1982.
  32. R. P. Singh, K. N. C. Murthy, and G. K. Jayaprakasha, “Studies on the antioxidant activity of pomegranate (Punica granatum) peel and seed extracts using in vitro models,” Journal of Agricultural and Food Chemistry, vol. 50, no. 1, pp. 81–86, 2002. View at Publisher · View at Google Scholar · View at Scopus
  33. C. Praveen, A. Ayyanar, and P. T. Perumal, “Practical synthesis, anticonvulsant, and antimicrobial activity of N-allyl and N-propargyl di(indolyl)indolin-2-ones,” Bioorganic & Medicinal Chemistry Letters, vol. 21, no. 13, pp. 4072–4077, 2011. View at Publisher · View at Google Scholar · View at Scopus
  34. K. Mruthunjaya and V. I. Hukkeri, “In vitro antioxidant and free radical scavenging potential of Parkinsonia aculeata Linn,” Pharmacognosy Magazine, vol. 4, no. 13, pp. 42–51, 2008. View at Google Scholar · View at Scopus
  35. J. C. M. Barreira, I. C. F. R. Ferreira, M. B. P. P. Oliveira, and J. A. Pereira, “Antioxidant activity and bioactive compounds of ten Portuguese regional and commercial almond cultivars,” Food and Chemical Toxicology, vol. 46, no. 6, pp. 2230–2235, 2008. View at Publisher · View at Google Scholar · View at Scopus