Table of Contents Author Guidelines Submit a Manuscript
Bioinorganic Chemistry and Applications
Volume 2006, Article ID 68274, 9 pages
http://dx.doi.org/10.1155/BCA/2006/68274

Structure-Activity Relationships of Synthetic Coumarins as HIV-1 Inhibitors

1Department of Chemistry, Faculty of Pharmacy, Medical University, 2 Dunav Street, Sofia 1000, Bulgaria
2Department of Virology, National Center of Infectious and Parasitic Diseases, 44A Stoletor Street, Sofia 1233, Bulgaria

Received 12 October 2004; Revised 9 March 2005; Accepted 12 March 2005

Copyright © 2006 I. Kostova 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. K-H Lee and S Morris-Natschke, “Recent advances in the discovery and development of plant-derived natural products and their analogs as anti-HIV agents,” Pure and Applied Chemistry, vol. 71, no. 6, pp. 1045–1052, 1999. View at Google Scholar
  2. Y Kashman, K R Gustafson, R W Fuller et al., “HIV inhibitory natural products. Part 7. The calanolides, a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum,” Journal of Medicinal Chemistry, vol. 35, no. 15, pp. 2735–2743, 1992. View at Publisher · View at Google Scholar · View at PubMed
  3. T Creagh, J L Ruckle, D T Tolbert et al., “Safety and pharmacokinetics of single doses of (+)-calanolide A, a novel, naturally occurring nonnucleoside reverse transcriptase inhibitor, in healthy, human immunodeficiency virus-negative human subjects,” Antimicrobial Agents and Chemotherapy, vol. 45, no. 5, pp. 1379–1386, 2001. View at Publisher · View at Google Scholar · View at PubMed
  4. Z-Q Xu, M T Flavin, and T R Jenta, “Calanolides, the naturally occurring anti-HIV agents,” Current Opinion in Drug Discovery & Development, vol. 3, no. 2, pp. 155–166, 2000. View at Google Scholar
  5. M T Flavin, J D Rizzo, A Khilevich et al., “Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers,” Journal of Medicinal Chemistry, vol. 39, no. 6, pp. 1303–1313, 1996. View at Publisher · View at Google Scholar · View at PubMed
  6. A Kucherenko, M T Flavin, W A Boulanger et al., “Novel approach for synthesis of (±)-calanolide A and its anti-HIV activity,” Tetrahedron Letters, vol. 36, no. 31, pp. 5475–5478, 1995. View at Google Scholar
  7. K Rehder and J Kepler, “Total synthesis of (+)-calanolide A,” Synthetic Communications, vol. 26, no. 21, pp. 4005–4021, 1996. View at Google Scholar
  8. D E Zembower, S Liao, M T Flavin et al., “Structural analogues of the calanolide anti-HIV agents. Modification of the trans-10,11-dimethyldihydropyran-12-ol ring (ring C),” Journal of Medicinal Chemistry, vol. 40, no. 6, pp. 1005–1017, 1997. View at Publisher · View at Google Scholar · View at PubMed
  9. B Chenera, M L West, J A Finkelstein, and G B Dreyer, “Total synthesis of (±)-calanolide A, a non-nucleoside inhibitor of HIV-1 reverse transcriptase,” The Journal of Organic Chemistry, vol. 58, no. 21, pp. 5605–5606, 1993. View at Publisher · View at Google Scholar
  10. S Gaddam, A Khilevich, C Filer et al., “Synthesis of dual 14C-labeled (+)-calanolide A, a naturally occurring anti-HIV agent,” Journal of Labelled Compounds and Radiopharmaceuticals, vol. 39, no. 11, pp. 901–906, 1997. View at Publisher · View at Google Scholar
  11. A Khilevich, A Mar, M T Flavin et al., “Synthesis of (+)-calanolide A, an anti-HIV agent, Via enzyme-catalyzed resolution of the aldol products,” Tetrahedron: Asymmetry, vol. 7, no. 11, pp. 3315–3326, 1996. View at Publisher · View at Google Scholar
  12. D L Galinis, R W Fuller, T C McKee et al., “Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and ()-calanolide B,” Journal of Medicinal Chemistry, vol. 39, no. 22, pp. 4507–4510, 1996. View at Publisher · View at Google Scholar · View at PubMed
  13. A Khilevich, J Rizzo, M T Flavin et al., “A versatile approach for synthesis of 2,3-dimethyl chroman-4-ones, intermediate for calanolide Anti-HIV agents, via aldol/mitsunobu reactions,” Synthetic Communications, vol. 26, no. 20, pp. 3757–3771, 1996. View at Google Scholar
  14. C J Palmer and J L Josephs, “Synthesis of the Calophyllum coumarins. Part 2,” Journal of the Chemical Society. Perkin Transactions 1, no. 24, pp. 3135–3152, 1995. View at Publisher · View at Google Scholar
  15. C J Palmer and J L Josephs, “Synthesis of the calophyllum coumarins,” Tetrahedron Letters, vol. 35, no. 30, pp. 5363–5366, 1994. View at Publisher · View at Google Scholar
  16. Z-Q Xu, E R Kern, L Westbrook et al., “Plant-derived and semi-synthetic calanolide compounds with in vitro activity against both human immunodeficiency virus type 1 and human cytomegalovirus,” Antiviral Chemistry & Chemotherapy, vol. 11, no. 1, pp. 23–29, 2000. View at Google Scholar · View at PubMed
  17. J H II Cardellina, H R Bokesch, T C McKee, and M R Boyd, “Resolution and comparative anti-HIV evaluation of the enantiomers of calanolides A and B,” Bioorganic & Medicinal Chemistry Letters, vol. 5, no. 9, pp. 1011–1014, 1995. View at Google Scholar
  18. P P Deshpande, F Tagliaferri, S F Victory, S Yan, and D C Baker, “Synthesis of optically active calanolides A and B,” The Journal of Organic Chemistry, vol. 60, no. 10, pp. 2964–2965, 1995. View at Publisher · View at Google Scholar
  19. T C McKee, J H II Cardellina, G B Dreyer, and M R Boyd, “The pseudocalanolides: structure revision of calanolides C and D,” Journal of Natural Products, vol. 58, no. 6, pp. 916–920, 1995. View at Publisher · View at Google Scholar · View at PubMed
  20. Z-Q Xu, R W Jr Buckheit, T L Stup et al., “In vitro anti-human immunodeficiency virus (HIV) activity of the chromanone derivative, 12-oxocalanolide A, a novel NNRTI,” Bioorganic & Medicinal Chemistry Letters, vol. 8, no. 16, pp. 2179–2184, 1998. View at Google Scholar · View at PubMed
  21. D Yu, M Suzuki, L Xie, S L Morris-Natschke, and K-H Lee, “Recent progress in the development of coumarin derivatives as potent anti-HIV agents,” Medicinal Research Reviews, vol. 23, no. 3, pp. 322–345, 2003. View at Publisher · View at Google Scholar · View at PubMed
  22. L Huang, Y Kashiwada, L M Cosentino et al., “Anti-AIDS agents. 15. Synthesis and anti-HIV activity of dihydroseselins and related analogs,” Journal of Medicinal Chemistry, vol. 37, no. 23, pp. 3947–3955, 1994. View at Publisher · View at Google Scholar · View at PubMed
  23. Z-Y Yang, Y Xia, P Xia, A Brossi, L M Cosentino, and K-H Lee, “Anti-AIDS agents. Part 41: synthesis and anti-HIV activity of 3,4-di-o-()-camphanoyl-(+)-cis-khellactone (DCK) lactam analogues,” Bioorganic & Medicinal Chemistry Letters, vol. 10, no. 10, pp. 1003–1005, 2000. View at Google Scholar · View at PubMed
  24. L Xie, Y Takeuchi, L M Cosentino, A T McPhail, and K-H Lee, “Anti-AIDS agents. 42. Synthesis and anti-HIV activity of disubstituted (3R,4R)-3,4-Di-O-(S)-camphanoyl-(+)-cis-khellactone analogues,” Journal of Medicinal Chemistry, vol. 44, no. 5, pp. 664–671, 2001. View at Publisher · View at Google Scholar · View at PubMed
  25. L Xie, D Yu, C Wild et al., “Anti-AIDS agents. 52. Synthesis and anti-HIV activity of hydroxymethyl (3R,4R)-3,4-Di-O-(S)-camphanoyl-(+)-cis-khellactone derivatives,” Journal of Medicinal Chemistry, vol. 47, no. 3, pp. 756–760, 2004. View at Publisher · View at Google Scholar · View at PubMed
  26. L Xie, Y Takeuchi, L M Cosentino, and K-H Lee, “Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3R,4R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents,” Journal of Medicinal Chemistry, vol. 42, no. 14, pp. 2662–2672, 1999. View at Publisher · View at Google Scholar · View at PubMed
  27. L Xie, G Allaway, C Wild, N Kilgore, and K-H Lee, “Anti-AIDS agents. Part 47: Synthesis and anti-HIV activity of 3-substituted 3,4-Di-O-(S)-camphanoyl-(3R,4R)-(+)-cis-khellactone derivatives,” Bioorganic & Medicinal Chemistry Letters, vol. 11, no. 17, pp. 2291–2293, 2001. View at Google Scholar · View at PubMed
  28. I V Martyanov, O D Zakharova, E Sottofattori et al., “Interaction of oligonucleotides conjugated to substituted chromones and coumarins with HIV-1 reverse transcriptase,” Antisense & Nucleic Acid Drug Development, vol. 9, no. 5, pp. 473–480, 1999. View at Google Scholar · View at PubMed
  29. I V Martyanov, O D Zakharova, E Sottofattori et al., “HIV-1 reverse transcriptase is capable of elongating derivatives of sequence specific noncomplementary oligodeoxynucleotides,” Biochemistry and Molecular Biology International, vol. 45, no. 5, pp. 857–864, 1998. View at Google Scholar · View at PubMed
  30. T Ishikawa, K Kotake, and H Ishii, “Synthesis of toddacoumaquinone, a coumarin-naphthoquinone dimer, and its antiviral activities,” Chemical & Pharmaceutical Bulletin, vol. 43, no. 6, pp. 1039–1041, 1995. View at Google Scholar · View at PubMed
  31. H I El-Subbagh, S M Abu-Zaid, M A Mahran, F A Badria, and A M Al-Obaid, “Synthesis and biological evaluation of certain α,β-unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents,” Journal of Medicinal Chemistry, vol. 43, no. 15, pp. 2915–2921, 2000. View at Publisher · View at Google Scholar · View at PubMed
  32. A S Bourinbaiar, X Tan, and R Nagorny, “Inhibitory effect of coumarins on HIV-1 replication and cell-mediated or cell-free viral transmission,” Acta Virologica, vol. 37, no. 4, pp. 241–250, 1993. View at Google Scholar · View at PubMed
  33. H Zhao, N Neamati, H Hong et al., “Coumarin-based inhibitors of HIV integrase,” Journal of Medicinal Chemistry, vol. 40, no. 2, pp. 242–249, 1997. View at Publisher · View at Google Scholar · View at PubMed
  34. H X Wang and T B Ng, “Examination of lectins, polysaccharopeptide, polysaccharide, alkaloid, coumarin and trypsin inhibitors for inhibitory activity against human immunodeficiency virus reverse transcriptase and glycohydrolases,” Planta Medica, vol. 67, no. 7, pp. 669–672, 2001. View at Publisher · View at Google Scholar · View at PubMed
  35. P C-M Mao, J-F Mouscadet, H Leh, C Auclair, and L-Y Hsu, “Chemical modification of coumarin dimer and HIV-1 integrase inhibitory activity,” Chemical & Pharmaceutical Bulletin, vol. 50, no. 12, pp. 1634–1637, 2002. View at Google Scholar · View at PubMed
  36. E A Lunney, S E Hagen, J M Domagala et al., “A novel nonpeptide HIV-1 protease inhibitor: elucidation of the binding mode and its application in the design of related analogs,” Journal of Medicinal Chemistry, vol. 37, no. 17, pp. 2664–2677, 1994. View at Publisher · View at Google Scholar · View at PubMed
  37. 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,” IL Farmaco, vol. 57, no. 9, pp. 703–708, 2002. View at Publisher · View at Google Scholar · View at PubMed
  38. M C Reboud-Ravaux, N D Boggetto, C E Doucet et al., “Synthetic inhibitors targeting serine and aspartic acid proteases,” Journal de Pharmacie de Belgique, vol. 51, no. 3, pp. 161–164, 1996 (French). View at Google Scholar · View at PubMed