Chromone and chromanone derivatives as strand transfer inhibitors of HIV-1 integrase

Archives of Pharmacal Research

Volumn 31, Issue 1, 2008, Pages 1-5

  Park, Jang Hyun ^a   Lee, Seung Uk ^a   Kim, Sang Hoon ^b   Shin, Seo Yeong ^b   Lee, Jae Yeol ^b   Shin, Cha Gyun ^c   Yoo, Kyung Ho ^a   Lee, Yong Sup ^b  

^a Korea Institute of Science and Technology   (South Korea)

^b Kyung Hee University   (South Korea)

^c Chung Ang University   (South Korea)

Author keywords

Chromanone; Chromone; Conformationally constrained; HIV 1 integrase inhibitor; Strand transfer

Indexed keywords

ANTHRAQUINONE DERIVATIVE; CHROMANONE; CHROMONE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; INTEGRASE INHIBITOR; UNCLASSIFIED DRUG; VIRUS DNA;

ARTICLE; CHEMISTRY; CONFORMATION; DRUG EFFECT; ENZYMOLOGY; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ANTHRAQUINONES; CHROMONES; DNA, VIRAL; HIV INTEGRASE INHIBITORS; HIV-1; HYDROGEN BONDING; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION;

EID: 40349108643     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-008-1111-z     Document Type: Article

References (16)

1. Appleton, R. A., Bantick, J. R., Chamberlain, T. R., Hardern, D. N., Lee, T. B., and Pratt, A. D., Antagonists of slow reacting substance of anaphylaxis. Synthesis of a series of chromone-2-carboxylic acids. J. Med. Chem., 20, 371-379 (1977).
2. Barreca, M. L., Ferro, S., Rao, A., De Luca, L., Zappalà, M., Monforte, A.-M., Debyser, Z., Witvrouw, M., and Chimirri, A., Pharmacophore-based design of HIV-1 integrase strand-transfer inhibitors. J. Med. Chem. 48, 7084-7088 (2005).
3. Barre-Sinoussi, F., Chermann, J. C., Rey, F., Nugeyre, M. T., Chamaret, S., Gruest, J., Dauguet, C., Axler-Blin, C., Vezinet-Brun, F., Rouzioux, C., Rozenbaum, W., and Montagnier, L., Isolation of a T-lymphotropic retrovirus from a patient at risk for acquired immune deficiency syndrome (AIDS). Science 220, 868-871 (1983).
4. Brown, P. O., Integration of retroviral DNA. Curr. Top. Microbiol. Immunol., 157, 19-48 (1990).
5. 4 antagonists. Bioorg. Med. Chem. Lett., 4, 2883-2888 (1994).
6. Engelman, A., Englund, G., Orenstein, J. M., Martin, M. A., and Craigie, R., Multiple effects of mutations in human immuno-deficiency virus type 1 integrase on viral replication. J. Virol., 69, 2729-2736 (1995).
7. Foehlisch, B., New chromone synthesis. Chemische Berichte, 104, 348-349 (1971).
8. Grobler, J. A., Stillmock, K., Hu, B., Witmer, M., Felock, P., Espeseth, A. S., Wolfe, A., Egbertson, M., Bourgeois, M., Melamed, J., Wai, J. S., Young, S., Vacca, J., and Hazuda, D. J., Diketo acid inhibitor mechanism and HIV-1 integrase: implications for metal binding in the active site of phosphotransferase enzymes. Proc. Natl. Acad. Sci. U.S.A., 99, 6661-6666 (2002).
9. Hazuda, D. J., Felock, P., Witmer, M., Wolfe, A., Stillmock, K., Grobler, J. A., Espeseth, A., Gabryelski, L., Schleif, W., Blau, C., and Miller, M. D., Inhibitors of strand transfer that prevent integration and inhibit HIV-1 replication in cells. Science, 287, 646-650 (2000).
10. Kang, J.-H., Kim, S. Y., Lee, J., Marquez, V. E., Lewin, N. E., Pearce, L. V., and Blumberg, P. M., Macrocyclic diacylglycerol-bis-lactones as conformationally constrained analogues of diacylglycerol-lactones. Interactions with protein kinase C, J. Med. Chem., 47, 4000-4007 (2004).
11. Lee, S. U., Park, J. H., Kwon, T. H., Yoo, Y. J., Lee, J. Y., Shin, C.-G., Yoo, K. H., and Lee, Y. S., Synthesis and HIV-1 integrase inhibitory activities of 4-hydroxy-5-azacoumarin 3-carboxamides. Bull. Korean Chem. Soc., 28, 1510-1514 (2007).
12. Pais, G. C. G., Zhang, X., Marchand, C., Neamati, N., Cowansage, K., Svarovskaia, E. S., Pathak, V. K., Tang, Y., Nicklaus, M., Pommier, Y., and Burke, T. R., Jr. Structure activity of 3-aryl-1,3-diketo-containing compounds as HIV-1 integrase inhibitors. J. Med. Chem., 45, 3184-3194 (2002).
13. Pommier, Y., Neamati, N., Inhibitors of human immuno-deficiency virus integrase. Adv. Virus Res., 52, 427-458 (1999).
14. Tanada, Y. and Mori, K., Synthesis and absolute configuration of (-)-neuchromenin, a neurotrophic metabolite of Eupenicillium javanicum var. meloforme, and its enantiomer. Eur. J. Org. Chem. 1963 (2001).
15. Wai, J. S., Egbertson, M. S., Payne, L. S., Fisher, T. E., Embrey, M. W., Tran, L. O., Melamed, J. Y., Langford, H. M., Guare, J. P., Jr., Zhuang, L., Grey, V. E., Vacca, J. P., Holloway, M. K., Naylor-Olsen, A. M., Hazuda, D. J., Felock, P. J., Wolfe, A. L., Stillmock, K. A., Schleif, W. A., Gabryelski, L. J., and Young, S. D., 4-Aryl-2,4-dioxobutanoic acid inhibitors of HIV-1 integrase and viral replication in cells. J. Med. Chem., 43, 4923-4926 (2000).
16. Zhang, X., Neamati, N., Lee, Y. K., Orr, A., Brown, R. D., Whitaker, N., Pommier, Y., and Burke, T. R. Jr., Arylisothiocyanate-containing esters of caffeic acid designed as affinity ligands for HIV-1 integrase. Bioorg. Med. Chem., 9, 1649-1657 (2001).