3-phenylcoumarins as inhibitors of HIV-1 replication

Molecules

Volumn 17, Issue 8, 2012, Pages 9245-9257

  Olmedo, Dionisio ^a,b   Sancho, Rocío ^c   Bedoya, Luis M ^d   López Pérez, José L ^a   Del Olmo, Esther ^a   Muñoz, Eduardo ^c   Alcamí, José ^d   Gupta, Mahabir P ^b   Feliciano, Arturo San ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b CIFLORPAN   (Panama)

^c UNIVERSITY OF CÓRDOBA   (Spain)

^d INSTITUTO DE SALUD CARLOS III   (Spain)

Author keywords

3 phenylcoumarins; AIDS; Anti HIV activity; NF B inhibition; Tat protein

Indexed keywords

4 PHENYLCOUMARIN; 4-PHENYLCOUMARIN; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; COUMARIN DERIVATIVE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LUCIFERASE; TRANSACTIVATOR PROTEIN; TUMOR NECROSIS FACTOR ALPHA;

ARTICLE; BIOSYNTHESIS; CELL LINE; DRUG ANTAGONISM; DRUG EFFECT; GENETIC TRANSCRIPTION; GENETICS; HELA CELL; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; PHYSIOLOGY; REPORTER GENE; SYNTHESIS; VIRUS REPLICATION;

ANTI-HIV AGENTS; CELL LINE; COUMARINS; GENES, REPORTER; HELA CELLS; HIV-1; HUMANS; INHIBITORY CONCENTRATION 50; LUCIFERASES; NF-KAPPA B; TAT GENE PRODUCTS, HUMAN IMMUNODEFICIENCY VIRUS; TRANSCRIPTION, GENETIC; TUMOR NECROSIS FACTOR-ALPHA; VIRUS REPLICATION;

EID: 84865465561     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17089245     Document Type: Article

References (46)

1. Piot, P.; Bartos, M.; Ghys, P.D.; Walker, N.; Schwartlander, B. The global impact of HIV/AIDS. Nature 2001, 410, 968-973.
2. Center for HIV Information, HIV InSite. Report on the Global HIV/AIDS Epidemic, UNAIDS (2011). Available online: http://hivinsite.ucsf.edu/(accessed on 25 July 2012).
3. Shen, L.; Siliciano, R.F. Viral reservoirs, residual viremia, and the potential of highly active antiretroviral therapy to eradicate HIV infection. J. Allergy Clin. Immunol. 2008, 122, 22-28.
4. Coiras, M.; López-Huertas, M.R.; Pérez-Olmeda, M.; Alcamí, J. Understanding HIV-1 latency provides clues for the eradication of long-term reservoirs. Nat. Rev. Microbiol. 2009, 7, 798-812.
5. Barouch, D.H. Challenges in the development of an HIV-1 vaccine. Nature 2008, 455, 613-619.
6. Adamson, C.S.; Freed, E.O. Recent progress in antiretrovirals - Lessons from resistance. Drug Discov. Today 2008, 13, 424-432.
7. Rabson, A.B.; Lin, H.C. NF-kappa B and HIV: Linking viral and immune activation. Adv. Pharmacol. 2000, 48, 161-207.
8. Alcami, J.; Lain de Lera, T.; Folgueira, L.; Pedraza, M.A.; Jacque, J.M.; Bachelerie, F.; Noriega, A.R.; Hay, R.T.; Harrich, D.; Gaynor, R.B.; et al. Absolute dependence on kappa B responsive elements for initiation and Tat-mediated amplification of HIV transcription in blood CD4 T lymphocytes. EMBO J. 1995, 14, 1552-1560.
9. Coiras, M.; López-Huertas, M.R.; Pérez-Olmeda, M.; Alcamí, J. Understanding HIV-1 latency provides clues for the eradication of long-term reservoirs. Nat. Rev. Microbiol. 2009, 7, 798-812.
10. Stevenson, M. Tat's seductive side. Nat. Med. 2003, 9, 163-164.
11. Karin, M.; Yamamoto, Y.; Wang, Q.M. The IKK NF-kappa B system: A treasure trove for drug development. Nat. Rev. Drug Discov. 2004, 3, 17-26.
12. Musa, M.A.; Cooperwood, J.S.; Khan, M.O. A review of coumarin derivatives in pharmacotherapy of breast cancer. Curr. Med. Chem. 2008, 15, 2664-2679.
13. Kulkarni, M.V.; Kulkarni, G.M.; Lin, C.H.; Sun, C.M. Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents. Curr. Med. Chem. 2006, 13, 2795-2818.
14. Sashidhara, K.V.; Kumar, A.; Chatterjee, M.; Rao, K.B.; Singh, S.; Verma, A.K.; Palit, G. Discovery and synthesis of novel 3-phenylcoumarin derivatives as antidepressant agents. Bioorg. Med. Chem. Lett. 2011, 21, 1937-1941.
15. Quezada, E.; Delogu, G.; Picciau, C.; Santana, L.; Podda, G.; Borges, F.; García-Morales, V.; Viña, D.; Orallo, F. Synthesis and vasorelaxant and platelet antiaggregatory activities of a new series of 6-halo-3-phenylcoumarins. Molecules 2010, 15, 270-279.
16. Matos, M.J.; Viña, D.; Janeiro, P.; Borges, F.; Santana, L.; Uriarte, E. New halogenated 3-phenylcoumarins as potent and selective MAO-B inhibitors. Bioorg. Med. Chem. Lett. 2010, 20, 5157-5160.
17. Matos, M.J.; Viña, D.; Quezada, E.; Picciau, C.; Delogu, G.; Orallo, F.; Santana, L.; Uriarte, E. A new series of 3-phenylcoumarins as potent and selective MAO-B inhibitors. Bioorg. Med. Chem. Lett. 2009, 19, 3268-3270.
18. Matos, M.J.; Vina, D.; Picciau, C.; Orallo, F.; Santana, L.; Uriarte, E. Synthesis and evaluation of 6-methyl-3-phenylcoumarins as potent and selective MAO-B inhibitors. Bioorg. Med. Chem. Lett. 2009, 19, 5053-5055.
19. Roussaki, M.; Kontogiorgis, C.A.; Hadjipavlou-Litina, D.; Hamilakis, S.; Detsi, A. A novel synthesis of 3-aryl coumarins and evaluation of their antioxidant and lipoxygenase inhibitory activity. Bioorg. Med. Chem. Lett. 2010, 20, 3889-3892.
20. Belluti, F.; Fontana, G.; dal Bo, L.; Carenini, N.; Giommarelli, C.; Zunino, F. Design, synthesis and anticancer activities of stilbene-coumarin hybrid compounds: Identification of novel proapoptotic agents. Bioorg. Med. Chem. 2010, 18, 3543-3550.
21. Riveiro, M.E.; Moglioni, A.; Vazquez, R.; Gomez, N.; Facorro, G.; Piehl, L.; de Celis, E.R.; Shayo, C.; Davio, C. Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells. Bioorg. Med. Chem. 2008, 16, 2665-2675.
22. Kostova, I.; Raleva, S.; Genova, P.; Argirova, R. Structure-activity relationships of synthetic coumarins as HIV-1 inhibitors. Bioinorg. Chem. Appl. 2006, 2006, 68274:1-68274:9.
23. Kostova, I. Coumarins as inhibitors of HIV reverse transcriptase. Curr. HIV Res. 2006, 4, 347-363.
24. Mastrolorenzo, A.; Rusconi, S.; Scozzafava, A.; Barbaro, G.; Supuran, C.T. Inhibitors of HIV-1 protease: Current state of the art 10 years after their introduction. From antiretroviral drugs to antifungal, antibacterial and antitumor agents based on aspartic protease inhibitors. Curr. Med. Chem. 2007, 14, 2734-2748.
25. Kashman, Y.; Gustafson, K.R.; Fuller, R.W.; Cardellina, J.H., 2nd; McMahon, J.B.; Currens, M.J.; Buckheit, R.W., Jr.; Hughes, S.H.; Cragg, G.M.; Boyd, M.R. The calanolides, a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum. J. Med. Chem. 1992, 35, 2735-2743.
26. Patil, A.D.; Freyer, A.J.; Eggleston, D.S.; Haltiwanger, R.C.; Bean, M.F.; Taylor, P.B.; Caranfa, M.J.; Breen, A.L.; Bartus, H.R.; Johnson, R.K.; et al. The inophyllums, novel inhibitors of HIV-1 reverse transcriptase isolated from the Malaysian tree, Calophyllum inophyllum L. J. Med. Chem. 1993, 36, 4131-4138.
27. Al-Mawsawi, L.Q.; Fikkert, V.; Dayam, R.; Witvrouw, M.; Burke, T.R., Jr.; Borchers, C.H.; Neamati, N. Discovery of a small-molecule HIV-1 integrase inhibitor-binding site. Proc. Natl. Acad. Sci. USA 2006, 103, 10080-10085.
28. Chiang, C.C.; Mouscadet, J.F.; Tsai, H.J.; Liu, C.T.; Hsu, L.Y. Synthesis and HIV-1 integrase inhibition of novel bis- or tetra-coumarin analogues. Chem. Pharm. Bull. 2007, 55, 1740-1743.
29. Uchiumi, F.; Hatano, T.; Ito, H.; Yoshida, T.; Tanuma, S. Transcriptional suppression of the HIV promoter by natural compounds. Antiviral Res. 2003, 58, 89-98.
30. Ma, T.; Gao, Q.; Chen, Z.; Wang, L.; Liu, G. Chemical resolution of (±)-calanolide A, (±)-cordatolide A and their 11-demethyl analogues. Bioorg. Med. Chem. Lett. 2008, 18, 1079-1083.
31. Kirkiacharian, S.; Thuy, D.T.; Sicsic, S.; Bakhchinian, R.; Kurkjian, R.; Tonnaire, T. Structure-activity relationships of some 3-substituted-4- hydroxycoumarins as HIV-1 protease inhibitors. Farmaco 2002, 57, 703-708.
32. Bedoya, L.M.; Beltran, M.; Sancho, R.; Olmedo, D.A.; Sanchez-Palomino, S.; del Olmo, E.; López-Pérez, J.L.; Muñoz, E.; San Feliciano, A.; Alcami, J. 4-Phenylcoumarins as HIV transcription inhibitors. Bioorg. Med. Chem. Lett. 2005, 15, 4447-4450.
33. Márquez, N.; Sancho, R.; Bedoya, L.M.; Alcamí, J.; López-Pérez, J.L.; San Feliciano, A.; Fiebich, B.L.; Muñoz, E. Mesuol, a natural occurring 4-phenylcoumarin, inhibits HIV-1 replication by targeting the NF-kappaB pathway. Antiviral Res. 2005, 66, 137-145.
34. López-Pérez, J.L.; Olmedo, D.A.; del Olmo, E.; Vásquez, Y.; Solis, P.N.; Gupta, M.P.; San Feliciano, A. Cytotoxic 4-phenylcoumarins from the leaves of Marila pluricostata. J. Nat. Prod. 2005, 68, 369-373.
35. Mohanty, S.; Makrandi, J.K.; Grover, S.K. Phase-transfer catalyzed synthesis of 3-phenylcoumarins. Indian J. Chem. Sec. B 1989, 28, 766-767.
36. Deschamps-Vallet, C.; Ilotse, J.B.; Meyer-Dayan, M. Transformation of the isoflavylium cation into 3-phenylcoumarins, isoflav-3-enes, and isoflavans. Tetrahedron Lett. 1983, 24, 3993-3996.
37. Hans, N.; Singhi, M.; Sharma, V.; Grover, S.K. A novel one-step synthesis of 3-phenyl-, 4-methyl-3-phenyl- and 3-phenyl-4-styrylcoumarins using DCC-DMSO. Indian J. Chem. Sec. B Org. Chem. Incl. Med. Chem. 1996, 35B, 1159-1162.
38. Neelakantan, S.; Raman, P.V.; Tinabaye, A. A new and convenient synthesis of 4-methyl-3- phenyl-coumarins and 3-phenylcoumarins. Indian J. Chem. Sec. B 1982, 21, 256-257.
39. Kappe, T.; Brandner, A. A simple synthesis of coumestrol. Z. Naturforsch. 1974, 29, 292-293.
40. Stadlbauer, W.; Badawey, E.-S.; Hojas, G.; Roschger, P.; Kappe, T. Malonates in cyclocondensation reactions. Molecules 2001, 6, 338-352.
41. Sancho, R.; Medarde, M.; Sanchez-Palomino, S.; Madrigal, B.M.; Alcamí, J.; Munoz, E.; San Feliciano, A. Anti-HIV activity of some synthetic lignanolides and intermediates. Bioorg. Med. Chem. Lett. 2004, 14, 4483-4486.
42. Israel, N.; Gougerot-Pocidalo, M.A.; Aillet, F.; Virelizier, J.L. Redox status of cells influences constitutive or induced NF-kappa B translocation and HIV long terminal repeat activity in human T and monocytic cell lines. J. Immunol 1992, 149, 3386-3393.
43. García-Pérez, J.; Sánchez-Palomino, S.; Pérez-Olmeda, M.; Fernández, B.; Alcamí, J. A new strategy based on recombinant viruses as a tool for assessing drug susceptibility of human immunodeficiency virus type 1. J. Med. Virol. 2007, 79, 127-137.
44. Mhiri, C.; Ladhar, F.; El Gharbi, R.; Le Bigot, Y. A convenient synthesis of 3-arylcoumarins from arylacetonitriles. Synth. Commun. 1999, 29, 1451-1461.
45. Kamat, S.P.; D'Souza, A.M.; Paknikar, S.K.; Beauchamp, P.S. A convenient one-pot synthesis of 4-methyl-3-phenyl-, 3-aryl- and 3-aryl-4-phenylcoumarins. J. Chem. Res. Synop. 2002, 2002, 242-246.
46. Aparecido de Marchi, A.; Santos Castilho, M.; Barboni Nascimento, P.G.; Costa Archanjo, F.; del Ponte, G.; Oliva, G.; Tallarico Pupo, M. New 3-piperonylcoumarins as inhibitors of glycosomal glyceraldehyde-3-phosphate dehydrogenase (gGAPDH) from Trypanosoma cruzi. Bioorg. Med. Chem. 2004, 12, 4823-4833.