Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2015, Article ID 826489, 6 pages
http://dx.doi.org/10.1155/2015/826489
Research Article

Hydrolysis and Hydrazinolysis of Isatin-Based Ald- and Ketazines

1Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Egyptian Russian University, Badr City, Cairo 11829, Egypt
2Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
3Department of Applied Organic Chemistry, National Research Centre, Dokki, Cairo 12622, Egypt

Received 14 January 2015; Revised 10 April 2015; Accepted 17 April 2015

Academic Editor: Tanaji Talele

Copyright © 2015 Hany S. Ibrahim 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. K. Sridhar, M. Saravanan, and A. Ramesh, “Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives,” European Journal of Medicinal Chemistry, vol. 36, no. 7-8, pp. 615–625, 2001. View at Publisher · View at Google Scholar · View at Scopus
  2. A. Jarrahpour, J. Sheikh, I. E. Mounsi, H. Juneja, and T. B. Hadda, “Computational evaluation and experimental in vitro antibacterial, antifungal and antiviral activity of bis-Schiff bases of isatin and its derivatives,” Medicinal Chemistry Research, vol. 22, no. 3, pp. 1203–1211, 2013. View at Publisher · View at Google Scholar · View at Scopus
  3. T. N. Akhaja and J. P. Raval, “1,3-dihydro-2H-indol-2-ones derivatives: design, Synthesis, in vitro antibacterial, antifungal and antitubercular study,” European Journal of Medicinal Chemistry, vol. 46, no. 11, pp. 5573–5579, 2011. View at Publisher · View at Google Scholar · View at Scopus
  4. M. Verma, S. N. Pandeya, K. N. Singh, and J. P. Stables, “Anticonvulsant activity of Schiff bases of isatin derivatives,” Acta Pharmaceutica, vol. 54, no. 1, pp. 49–56, 2004. View at Google Scholar · View at Scopus
  5. S. K. Sridhar, S. N. Pandeya, J. P. Stables, and A. Ramesh, “Anticonvulsant activity of hydrazones, Schiff and Mannich bases of isatin derivatives,” European Journal of Pharmaceutical Sciences, vol. 16, no. 3, pp. 129–132, 2002. View at Publisher · View at Google Scholar · View at Scopus
  6. H. R. Lawrence, R. Pireddu, L. Chen et al., “Inhibitors of Src homology-2 domain containing protein tyrosine phosphatase-2 (Shp2) based on oxindole scaffolds,” Journal of Medicinal Chemistry, vol. 51, no. 16, pp. 4948–4956, 2008. View at Publisher · View at Google Scholar · View at Scopus
  7. A. H. Abadi, S. M. Abou-Seri, D. E. Abdel-Rahman, C. Klein, O. Lozach, and L. Meijer, “Synthesis of 3-substituted-2-oxoindole analogues and their evaluation as kinase inhibitors, anticancer and antiangiogenic agents,” European Journal of Medicinal Chemistry, vol. 41, no. 3, pp. 296–305, 2006. View at Publisher · View at Google Scholar · View at Scopus
  8. H. A. Abdel-Aziz, T. Elsaman, A. Al-Dhfyan, M. I. Attia, K. A. Al-Rashood, and A.-R. M. Al-Obaid, “Synthesis and anticancer potential of certain novel 2-oxo-N′-(2-oxoindolin- 3-ylidene)-2H-chromene-3-carbohydrazides,” European Journal of Medicinal Chemistry, vol. 70, pp. 358–363, 2013. View at Publisher · View at Google Scholar · View at Scopus
  9. H. E. Dweedar, H. Mahrous, H. S. Ibrahim, and H. A. Abdel-Aziz, “Analogue-based design, synthesis and biological evaluation of 3-substituted-(methylenehydrazono)indolin-2-ones as anticancer agents,” European Journal of Medicinal Chemistry, vol. 78, pp. 275–280, 2014. View at Publisher · View at Google Scholar · View at Scopus
  10. T. A. F. M. Hassan, A. A. Kadi, and H. A. K. Abdel-Aziz, “Novel N, N′-Hydrazino-bis-isatin Derivatives with Selective Activity against Multidrug-Resistant Cancer Cells,” US Patents, US20120252860, 2012.
  11. K. M. Khan, M. Khan, M. Ali et al., “Synthesis of bis-Schiff bases of isatins and their antiglycation activity,” Bioorganic & Medicinal Chemistry, vol. 17, no. 22, pp. 7795–7801, 2009. View at Publisher · View at Google Scholar · View at Scopus
  12. E. C. Gilbert, “Studies on hydrazine. the hydrolysis of dimethylketazine and the equilibrium between hydrazine and acetone,” Journal of the American Chemical Society, vol. 51, no. 11, pp. 3394–3409, 1929. View at Publisher · View at Google Scholar · View at Scopus
  13. A. C. Day and M. C. Whiting, “Acetone hydrazone,” Organic Syntheses, vol. 50, p. 3, 1970. View at Google Scholar
  14. V. K. Sharma, S. Srivastava, and A. Srivastava, “Novel coordination complexes of the trivalent ruthenium, rhodium and iridium with hydrazones derived from isatin hydrazide and various aldehydes with spectral and biological characterization,” Polish Journal of Chemistry, vol. 80, no. 3, pp. 387–396, 2006. View at Google Scholar · View at Scopus
  15. H. Eshghi and M. Hosseini, “Selective and convenient protection of aldehydes as azines under solvent-free conditions,” Journal of the Chinese Chemical Society, vol. 55, no. 3, pp. 636–638, 2008. View at Google Scholar · View at Scopus
  16. S. Okumura, C.-H. Lin, Y. Takeda, and S. Minakata, “Oxidative dimerization of (hetero)aromatic amines utilizing t-BuOI leading to (hetero)aromatic azo compounds: scope and mechanistic studies,” The Journal of Organic Chemistry, vol. 78, no. 23, pp. 12090–12105, 2013. View at Publisher · View at Google Scholar · View at Scopus
  17. K. M. Khan, W. Jamil, N. Ambreen, M. Taha, S. Perveen, and G. A. Morales, “An expeditious synthetic approach towards the synthesis of Bis-Schiff bases (aldazines) using ultrasound,” Ultrasonics Sonochemistry, vol. 21, no. 3, pp. 1200–1205, 2014. View at Publisher · View at Google Scholar · View at Scopus
  18. A.-F. E. Mourad, “Charge-transfer complexes of heterocyclic azines with Π-acceptors,” Spectrochimica Acta Part A, vol. 41, no. 1-2, pp. 347–350, 1985. View at Publisher · View at Google Scholar · View at Scopus
  19. K. Saito and H. Ishihara, “Thermolysis of sodium salts of tosylhydrazones of some heterocyclic aldehydes in the presence of silver chromate: 1,3 N→C migration of tosyl group,” Heterocycles, vol. 26, no. 7, pp. 1891–1898, 1987. View at Publisher · View at Google Scholar · View at Scopus
  20. L. Yang, X. Shan, Q. Chen, Z. Wang, and J. S. Ma, “The first silver(I) side-on η2-coordination network formed by self-assembly of bis(pyrrol-2-ylmethylene)hydrazine,” European Journal of Inorganic Chemistry, no. 7, pp. 1474–1477, 2004. View at Publisher · View at Google Scholar · View at Scopus
  21. E. H. Cordes and W. P. Jencks, “The mechanism of hydrolysis of Schiff bases derived from aliphatic amines,” Journal of the American Chemical Society, vol. 85, no. 18, pp. 2843–2848, 1963. View at Publisher · View at Google Scholar · View at Scopus