Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2013, Article ID 636280, 7 pages
http://dx.doi.org/10.1155/2013/636280
Research Article

Alkylation and 1,3-Dipolar Cycloaddition of 6-Styryl-4,5-dihydro-2H-pyridazin-3-one: Synthesis of Novel N-Substituted Pyridazinones and Triazolo[4,3-b]pyridazinones

1Laboratoire de Chimie Organique et Analytique, Faculté des Sciences et Techniques, Université Sultan Moulay Slimane, BP 523, Béni-Mellal, Morocco
2Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal
3Laboratoire de Diffraction des Rayons X, Centre Nationale pour la Recherche, Scientifique et Technique, Rabat, Morocco

Received 9 June 2012; Accepted 18 September 2012

Academic Editor: Julia Revuelta

Copyright © 2013 Souad Mojahidi 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. Demirayak, A. C. Karaburun, and R. Beis, “Some pyrrole substituted aryl pyridazinone and phthalazinone derivatives and their antihypertensive activities,” European Journal of Medicinal Chemistry, vol. 39, no. 12, pp. 1089–1095, 2004. View at Publisher · View at Google Scholar · View at Scopus
  2. A. A. Siddiqui, R. Mishra, and M. Shaharyar, “Synthesis, characterization and antihypertensive activity of pyridazinone derivatives,” European Journal of Medicinal Chemistry, vol. 45, no. 6, pp. 2283–2290, 2010. View at Publisher · View at Google Scholar · View at Scopus
  3. Z. K. Sweeney, J. P. Dunn, Y. Li et al., “Discovery and optimization of pyridazinone non-nucleoside inhibitors of HIV-1 reverse transcriptase,” Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 15, pp. 4352–4354, 2008. View at Publisher · View at Google Scholar · View at Scopus
  4. M. Sonmez, I. Borber, and E. Akbas, “Synthesis, antibacterial and antifungal activity of some new pyridazinone metal complexes,” European Journal of Medicinal Chemistry, vol. 41, no. 1, pp. 101–105, 2006. View at Publisher · View at Google Scholar
  5. L. Costantino, G. Rastelli, G. Cignarella, and D. Barlocco, “Synthesis and aldose reductase inhibitory activity of a new series of benzo[h]cinnolinone derivatives,” Farmaco, vol. 55, no. 8, pp. 544–552, 2000. View at Publisher · View at Google Scholar · View at Scopus
  6. S. K. Kwon and A. Moon, “Synthesis of 3-alkylthio-6-allylthiopyridazine derivatives and their antihepatocarcinoma activity,” Archives of Pharmacal Research, vol. 28, no. 4, pp. 391–394, 2005. View at Publisher · View at Google Scholar
  7. R. R. Harris, L. Black, S. Surapaneni et al., “ABT-963 [2-(3,4-difluoro-phenyl)-4-(3-hydroxy-3-methyl-butoxy)-5-(4- methanesulfonyl-phenyl)-2H-pyridazin-3-one], a highly potent and selective disubstituted pyridazinone cyclooxgenase-2 inhibitor,” Journal of Pharmacology and Experimental Therapeutics, vol. 311, no. 3, pp. 904–912, 2004. View at Publisher · View at Google Scholar · View at Scopus
  8. W. Malinka, A. Redzicka, and O. Lozach, “New derivatives of pyrrolo[3,4-d]pyridazinone and their anticancer effects,” Farmaco, vol. 59, no. 6, pp. 457–462, 2004. View at Publisher · View at Google Scholar · View at Scopus
  9. N. F. Abd El-Ghaffar, M. K. Mohamed, M. S. Kadah, A. M. Radwan, G. H. Said, and S. N. Abd el Al, “Synthesis and anti-tumor activities of some new pyridazinones containing the 2-phenyl-1H-indolyl moiety,” Journal of Chemical and Pharmaceutical Research, vol. 3, no. 3, pp. 248–259, 2011. View at Google Scholar · View at Scopus
  10. S. Mojahidi, E. M. Rakib, H. Sekkak et al., “Synthesis and in-vitro cytotoxic evaluation of novel pyridazin-4-one derivatives,” Archiv der Pharmazie, vol. 343, no. 5, pp. 310–313, 2010. View at Publisher · View at Google Scholar · View at Scopus
  11. H. Sekkak, S. Mojahidi, E. M. Rakib et al., “Synthesis and antiproliferative evaluation of spirothiadiazolopyridazine derivatives,” Letters in Drug Design and Discovery, vol. 7, no. 10, pp. 743–746, 2010. View at Google Scholar · View at Scopus
  12. S. Abouricha, E. M. Rakib, N. Benchat, M. Alaoui, H. Allouchi, and B. El Bali, “Facile synthesis of new spirothiadiazolopyridazines by 1,3-dipolar cycloaddition,” Synthetic Communications, vol. 35, no. 16, pp. 2213–2221, 2005. View at Publisher · View at Google Scholar · View at Scopus
  13. S. H. Zaheer, I. K. Kacker, and N. S. Rao, “Über die Kondensation von Lavulinsaure mit aromatischen Aldehyden,” Chemische Berichte, vol. 89, no. 2, pp. 351–354, 1956. View at Google Scholar
  14. I. Sircar, R. P. Steffen, G. Bobowski et al., “Cardiotonic agents. 9. Synthesis and biological evaluation of a series of (E)-4,5-dihydro-6-[2-[4-(1H-imidazol-1-yl)phenyl]ethenyl]-3(2H)-pyridazinones: a novel class of compounds with positive inotropic, antithrombotic, and vasodilatory activities for the treatment of congestive heart failure,” Journal of Medicinal Chemistry, vol. 32, no. 2, pp. 342–350, 1989. View at Google Scholar · View at Scopus
  15. R. Huisgen, “1,3-dipolar cycloadditions. Past and future,” Angewandte Chemie, vol. 2, no. 10, pp. 565–598, 1963. View at Publisher · View at Google Scholar
  16. R. Huisgen, “Kinetics and mechanism of 1,3-dipolar cycloadditions,” Angewandte Chemie, vol. 2, no. 11, pp. 633–645, 1963. View at Publisher · View at Google Scholar
  17. A. Padwa, Ed., 1,3-Dipolar Cycloaddition Chemistry, Wiley, New York, NY, USA, 1984.
  18. K. V. Gothelf and K. A. Jorgensen, “Asymmetric 1,3-dipolar cycloaddition reactions,” Chemical Reviews, vol. 98, no. 2, pp. 863–909, 1998. View at Publisher · View at Google Scholar
  19. A. Padwa and A. M. Schoffsttall, in Advances in Cycloaddition, D. P. Curran, Ed., vol. 2, pp. 1–89, JAI, London, UK, 1990.
  20. S. Kobayashi and K. A. Jorgensen, Eds., Cycloaddition Reactions in Organic Synthesis, Wiley-VCH, Weinheim, Germany, 2002.
  21. A. Padwa, Synthetic Applications of 1, 3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, John Wiley & Sons, 2002.
  22. D. B. Sharp and C. S. Hamilton, “Derivatives of 1,2,4-triazole and of pyrazole,” Journal of the American Chemical Society, vol. 68, no. 4, pp. 588–591, 1946. View at Google Scholar · View at Scopus