Table of Contents
ISRN Pharmaceutics
Volume 2011, Article ID 137637, 9 pages
http://dx.doi.org/10.5402/2011/137637
Research Article

Synthesis and Inhibiting Activity of Some 4-Hydroxycoumarin Derivatives on HIV-1 Protease

1Department of Chemistry, Faculty of Pharmacy, 2 Dunav Street, 1000 Sofia, Bulgaria
2Department of Chemistry, Faculty of Science, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark
3Laboratory of Virology, Faculty of Biology, Sofia University “St. Kliment Ohridski”, 8 Dragan Zankov, 1164 Sofia, Bulgaria
4Laboratory of Biocoordination and Bioanalytical Chemistry, Faculty of Chemistry, Sofia University “St. Kliment Ohridski”, 1 J. Bourchier, 1164 Sofia, Bulgaria
5Laboratory of Cell Cultures, National Center of Infectious and Parasitic Diseases, 44 A Stoletov Street, 1233 Sofia, Bulgaria
6Laboratory of Retroviruses, National Center of Infectious and Parasitic Diseases, 44 A Stoletov Street, 1233 Sofia, Bulgaria
7Department of Pharmaceutical Chemistry, Faculty of Pharmacy, 2 Dunav Street, 1000 Sofia, Bulgaria

Received 11 April 2011; Accepted 14 May 2011

Academic Editors: R. Cao, F. Fullas, P.-W. Hsieh, and S. Raic-Malic

Copyright © 2011 Stancho Stanchev 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. D. Nolan, “Metabolic complications associated with HIV protease inhibitor therapy,” Drugs, vol. 63, no. 23, pp. 2555–2574, 2003. View at Publisher · View at Google Scholar · View at Scopus
  2. J. H. Condra, W. A. Schleif, O. M. Blahy et al., “In vivo emergence of HIV-1 variants resistant to multiple protease inhibitors,” Nature, vol. 374, no. 6522, pp. 569–571, 1995. View at Publisher · View at Google Scholar · View at Scopus
  3. C. Hoffmann, “Overview of antiretroviral agents,” in HIV, C. Hoffmann and J. Rockstroh, Eds., pp. 62–107, Medizin Fokus, Hamburg 707 pages, 2010. View at Google Scholar
  4. P. J. Tummino, D. Ferguson, L. Hupe, and D. Hupe, “Competitive inhibition of HIV-1 protease by 4-hydroxy-benzopyran-2-ones and by 4-hydroxy-6-phenylpyran-2-ones,” Biochemical and Biophysical Research Communications, vol. 200, no. 3, pp. 1658–1664, 1994. View at Publisher · View at Google Scholar · View at Scopus
  5. I. Manolov, Z. Mladenova, Z. Raleva et al., “Positional isomerism confers anti-HIV activity of some 4-hydroxycoumarin (4-hc) derivatives in cell culture,” in Proceedings of the 15th International AIDS Conference, Bangkok, Thailand, July 2004.
  6. S. Kirkiacharian, D. T. Thuy, S. Sicsic, R. Bakhchinian, R. Kurkjian, and T. Tonnaire, “Structure-activity relationships of some 3-substituted-4-hydroxycoumarins as HIV-1 protease inhibitors,” Farmaco, vol. 57, no. 9, pp. 703–708, 2002. View at Publisher · View at Google Scholar · View at Scopus
  7. V. Hariprasad, T. T. Talele, and V. M. Kulkarni, “Design and synthesis of a novel series of nonpeptidic HIV-1 protease inhibitors,” Pharmacy and Pharmacology Communications, vol. 4, pp. 365–372, 1998. View at Google Scholar
  8. S. Thaisrivongs, P. K. Tomich, K. D. Watenpaugh et al., “Structure-based design of HIV protease inhibitors: 4-Hydroxycoumarins and 4-hydroxy-2-pyrones as non-peptidic inhibitors,” Journal of Medicinal Chemistry, vol. 37, no. 20, pp. 3200–3204, 1994. View at Publisher · View at Google Scholar · View at Scopus
  9. S. Kirkiacharian, D. T. Thuy, S. Sicsic, R. Bakhchinian, R. Kurkjian, and T. Tonnaire, “Structure-activity relationships of some 3-substituted-4-hydroxycoumarins as HIV-1 protease inhibitors,” Farmaco, vol. 57, no. 9, pp. 703–708, 2002. View at Publisher · View at Google Scholar · View at Scopus
  10. S. Stanchev, G. Momekov, F. Jensen, and I. Manolov, “Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives,” European Journal of Medicinal Chemistry, vol. 43, no. 4, pp. 694–706, 2008. View at Publisher · View at Google Scholar · View at Scopus
  11. S. Stanchev, F. Jensen, and I. Manolov, “Synthesis and DFT study of the spectral behavior of new 4-hydroxycoumarins,” International Journal of Quantum Chemistry, vol. 108, no. 8, pp. 1340–1351, 2008. View at Publisher · View at Google Scholar · View at Scopus
  12. T. Mosmann, “Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays,” Journal of Immunological Methods, vol. 65, no. 1-2, pp. 55–63, 1983. View at Google Scholar · View at Scopus
  13. B. Zuo, Q. Wang, Y. Wang, and Y. Ma, “Knoevenagel condensation over acidic zeolite,” Kex Chuban, vol. 23, pp. 555–558, 2002. View at Google Scholar
  14. B. Kuebel, “Simple synthesis of 4-(heteroarylmethyl)phenols and their acylation,” Liebigs Annalen der Chemie, vol. 9, pp. 1392–1401, 1980. View at Google Scholar
  15. R. Harima, K. Shimada, and T. Goto, “Usui M: α-Acetylcinnammates as fungicides,” Jap. Pat. 50154419, 1975.
  16. R. F. Luduena, M. C. Roach, V. Prasad et al., “Interaction of bovine brain tubulin with the 4(1H)-pyrizinone derivative IKP104, an antimitotic drug with a complex set of effects on the conformational stability of the tubulin molecule,” Biochemistry, vol. 34, no. 48, pp. 15751–15759, 1995. View at Publisher · View at Google Scholar · View at Scopus
  17. R. Pandya and K. Pandya, “The condensation of aldehides with β-oxoesthers. III. 3-Hydroxy-, 4-Hydroxy and 3,4-dihydroxybenzaldehides,” Journals of the Indian Chemical Society, vol. 39, pp. 231–237, 1957. View at Google Scholar
  18. R. Friesner, J. Banks, R. Murphy et al., “Maestro, Macromodel, Glide, XCluster, Schrødinger L.L.C,” Journal of Medicinal Chemistry, vol. 47, pp. 1739–1749, 2004. View at Google Scholar
  19. R. A. Broglia, D. Provasi, F. Vasile, G. Ottolina, R. Longhi, and G. Tiana, “A folding inhibitor of the HIV-1 protease,” Proteins, vol. 62, no. 4, pp. 928–933, 2006. View at Publisher · View at Google Scholar · View at Scopus
  20. D. C. Montefiori, W. E. Robinson, S. S. Schuffman, and W. M. Mitchell, “Evaluation of antiviral drugs and neutralizing antibodies to human immunodeficiency virus by a rapid and sensitive microtiter infection assay,” Journal of Clinical Microbiology, vol. 26, no. 2, pp. 231–235, 1988. View at Google Scholar · View at Scopus
  21. P. Harrigan, C. Stone, P. Griffin et al., “Resistance profile of human immunodeficiency virus—type 1 reverse transcriptase inhibitor abacavir (1592U89) after monotherapy and combination therapy. CNA Investigative Group,” Journal of Infectious Diseases, vol. 181, pp. 912–920, 2000. View at Google Scholar
  22. A. Hinkov, V. Atanasov, S. Raleva, and R. Argirova, “Modified rapid screening method for evaluation of HIV-1 protease inhibitors,” Comptes Rendus de L'Academie Bulgare des Sciences, vol. 63, no. 10, pp. 1455–1462, 2010. View at Google Scholar · View at Scopus