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The Scientific World Journal
Volume 2014, Article ID 427195, 10 pages
http://dx.doi.org/10.1155/2014/427195
Research Article

Nano-ZnO Catalyzed Multicomponent One-Pot Synthesis of Novel Spiro(indoline-pyranodioxine) Derivatives

Department of Chemistry, Faculty of Engineering and Technology, Mody Institute of Technology and Science, Lakshmangarh, Sikar, Rajasthan 332311, India

Received 24 August 2013; Accepted 18 November 2013; Published 5 February 2014

Academic Editors: E. Gomez-Bengoa, G. B. Shul’pin, and A. Silva

Copyright © 2014 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. T. R. Bal, B. Anand, P. Yogeeswari, and D. Sriram, “Synthesis and evaluation of anti-HIV activity of isatin β-thiosemicarbazone derivatives,” Bioorganic and Medicinal Chemistry Letters, vol. 15, no. 20, pp. 4451–4455, 2005. View at Publisher · View at Google Scholar · View at Scopus
  2. L. Chen, Y. Wang, W. L. Yi et al., “Synthesis and evaluation of isatin derivatives as effective SARS coronavirus 3CL protease inhibitors,” Bioorganic and Medicinal Chemistry Letters, vol. 15, no. 12, pp. 3058–3062, 2005. View at Publisher · View at Google Scholar · View at Scopus
  3. P. Selvam, M. Chandramohan, C. E. De, C. Pannecouque, and M. Witrouw, “Synthesis and anti-HIV activity of 4-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene) amino]-N(4,6-dimethyl-2-pyrimidinyl)-benzene sulfonamide and its derivatives,” European Journal of Pharmaceutical Sciences, vol. 14, pp. 313–316, 2001. View at Publisher · View at Google Scholar
  4. N. Sin, B. L. Venables, K. D. Combrink, H. B. Gulgeze, K. L. Yu, and R. L. Civiello, “Respiratory syncytial virus fusion inhibitors. Part 7: structure-activity relationships associated with a series of isatin oximes that demonstrate antiviral activity in vivo,” Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 16, pp. 4857–4862, 2009. View at Publisher · View at Google Scholar
  5. O. Guzel, N. Karali, and A. Salman, “Synthesis and antituberculosis activity of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives,” Bioorganic & Medicinal Chemistry, vol. 16, pp. 8976–8987, 2008. View at Publisher · View at Google Scholar
  6. N. Siddiqui, M. S. Alam, and W. Ahsan, “Synthesis, anticonvulsant and toxicity evaluation of 2-(1H-indol-3-yl) acetyl-N-(substituted phenyl)hydrazine carbothioamides and their related heterocyclic derivatives,” Acta Pharmaceutica, vol. 58, no. 4, pp. 445–454, 2008. View at Publisher · View at Google Scholar · View at Scopus
  7. I. Chiyanzu, C. Clarkson, P. J. Smith et al., “Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives,” Bioorganic & Medicinal Chemistry, vol. 13, no. 9, pp. 3249–3261, 2006. View at Google Scholar · View at Scopus
  8. S. Biswal, U. Sahoo, S. Sethy, H. K. S. Kumar, and M. Banerjee, “Indole: the molecule of diverse biological activities,” Asian Journal of Pharmaceutical and Clinical Research, vol. 5, no. 1, pp. 1–6, 2012. View at Google Scholar
  9. U. C. Mashelkar and D. M. Rane, “Synthesis of some isatin based novel spiroheterocycles and their biological activity studies,” Indian Journal of Chemistry B, vol. 44, no. 9, pp. 1937–1939, 2005. View at Google Scholar · View at Scopus
  10. K. C. Joshi, R. Jain, and P. Chand, “Indoles with C-3 as spiro atom,” Heterocycles, vol. 23, pp. 957–996, 1985. View at Publisher · View at Google Scholar
  11. B. L. Palucki, S. D. Feighner, S. Pong et al., “Spiro(indoline-3,4′-piperidine) growth hormone secretagogues as ghrelin mimetics,” Bioorganic and Medicinal Chemistry Letters, vol. 11, no. 14, pp. 1955–1957, 2001. View at Publisher · View at Google Scholar · View at Scopus
  12. B. Rajashekhar and E. T. Kaiser, “Design of biologically active peptides with non-peptidic structural elements. Biological and physical properties of a synthetic analogue of β-endorphin with unnatural amino acids in the region 6-12,” The Journal of Biological Chemistry, vol. 261, no. 29, pp. 13617–13623, 1986. View at Google Scholar · View at Scopus
  13. D. H. Rich and E. T. O. Sun, “Synthesis of analogs of the carboxyl protease inhibitor pepstatin. Effect of structure on inhibition of pepsin and renin,” Journal of Medicinal Chemistry, vol. 23, no. 1, pp. 27–33, 1980. View at Publisher · View at Google Scholar
  14. S. Vassiliou, A. Mucha, P. Cuniasse et al., “Phosphinic pseudo-tripeptides as potent inhibitors of matrix metalloproteinases: a structure-activity study,” Journal of Medicinal Chemistry, vol. 42, no. 14, pp. 2610–2620, 1999. View at Publisher · View at Google Scholar · View at Scopus
  15. S. J. Gould, “Streptonigrin,” Progress in the Chemistry of Organic Natural Products, vol. 41, pp. 77–114, 1982. View at Google Scholar · View at Scopus
  16. G. A. Kraus and P. K. Choudhury, “Synthesis of puraquinonic acid ethyl ester and deliquinone via a common intermediate,” Journal of Organic Chemistry, vol. 67, no. 16, pp. 5857–5859, 2002. View at Publisher · View at Google Scholar · View at Scopus
  17. H. Y. Shi, B. Deng, S. L. Zhong, L. Wang, and A. W. Xu, “Synthesis of zinc oxide nanoparticles with strong, tunable and stable visible light emission by solid-state transformation of Zn(II)-organic coordination polymers,” Journal of Materials Chemistry, vol. 21, pp. 12309–12315, 2011. View at Publisher · View at Google Scholar
  18. J. Safaei-Ghomi, M. A. Ghasemzadeh, and S. Zahedi, “ZnO nanoparticles: a highly effective and readily recyclable catalyst for the one-pot synthesis of 1, 8-dioxo-decahydroacridine and 1, 8-dioxooctahydro-xanthene derivatives,” Journal of the Mexican Chemical Society, vol. 57, no. 1, pp. 1–7, 2013. View at Google Scholar
  19. H. Alinezhad and S. Mohseni Tavakkoli, “Efficient and convenient synthesis of 1,8-dioxodecahydroacridine derivatives using Cu-doped ZnO nanocrystalline powder as a catalyst under solvent-free conditions,” The Scientific World Journal, vol. 2013, Article ID 575636, 9 pages, 2013. View at Publisher · View at Google Scholar
  20. F. M. Moghaddam, H. Saeidian, Z. Mirjafary, and A. Sadeghi, “Rapid and efficient one-pot synthesis of 1,4-dihydropyridine and polyhydroquinoline derivatives through the hantzsch four component condensation by zinc oxide,” Journal of the Iranian Chemical Society, vol. 6, no. 2, pp. 317–324, 2009. View at Google Scholar · View at Scopus
  21. F. Tamaddon, M. A. Amrollahi, and L. Sharafat, “A green protocol for chemoselective O-acylation in the presence of zinc oxide as a heterogeneous, reusable and eco-friendly catalyst,” Tetrahedron Letters, vol. 46, no. 45, pp. 7841–7844, 2005. View at Publisher · View at Google Scholar · View at Scopus
  22. B. V. Kumar, H. S. B. Naik, D. Girija, and B. V. Kumar, “ZnO nanoparticle as catalyst for efficient green one-pot synthesis of coumarins through Knoevenagel condensation,” Journal of Chemical Sciences, vol. 123, no. 5, pp. 615–621, 2011. View at Google Scholar · View at Scopus
  23. H. Sachdeva, D. Dwivedi, R. R. Bhattacharjee, S. Khaturia, and R. Saroj, “NiO nanoparticles: an efficient catalyst for the multicomponent one-pot synthesis of novel spiro and condensed indole derivatives,” Journal of Chemistry, vol. 2013, Article ID 606259, 10 pages, 2013. View at Publisher · View at Google Scholar
  24. K. Higashiyama and H. Otomasu, “Spiro heterocyclic compounds. III. Synthesis of spiro[oxindole-3, 4′-(4′H-pyran)]compounds,” Chemical and Pharmaceutical Bulletin, vol. 28, no. 2, pp. 648–651, 1980. View at Publisher · View at Google Scholar
  25. K. C. Joshi, R. Jain, K. Sharma, S. K. Bhattacharya, and R. K. Goel, “Studies in spiro-heterocycles. Part-XII. Synthesis of some fluorine containing spiro[3H-indole-3,4(4H)-pyrano[2,3-d]pyrimidine]-2,5,7(1H)-triones as CNS agents,” Journal of the Indian Chemical Society, vol. 115, pp. 202–204, 1988. View at Google Scholar
  26. Z. Sun, L. Liu, L. Zhang, and D. Jia, “Rapid synthesis of ZnO nano-rods by one-step, room-temperature, solid-state reaction and their gas-sensing properties,” Nanotechnology, vol. 17, no. 9, pp. 2266–2270, 2006. View at Publisher · View at Google Scholar · View at Scopus