Abstract
Triazolo-fused 3′,4′-cyclic nucleoside 4′-spiro nucleoside analogues were synthesized by an intramolecular 1,3-dipolar cycloaddition of 4′-azido nucleoside derived azido-alkynes in a regio- and stereo-specific manner. The thymine nucleoside base in these target compounds was transformed into the corresponding 5-methyl cytosine component. The synthesized compounds were examined in an MAGI(multinuclear-activation galactosidase indicator) assay for exploring the anti-HIV activity and in a H9 T(human T lymphocytes H9) assay for measuring the cell toxicity.
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de Clercq E., J. Clin. Vir., 2004, 30, 115
de Clercq E., Biochem. Pharm., 2007, 73, 911
de Clercq E., Biochim. Biophys. Acta, 2002, 1587, 258
de Clercq E., Biochem. Pharm., 2004, 68, 2301
Brady R. C., Bernstein D. I., Antivir Res., 2004, 61, 73
Papatheodoridis G. V., Dimou E., Papadimitropoulos V., Am. J. Gastroenterology, 2002, 97, 1618
Blagosklonny M. V., Cell Cycle, 2004, 3, 1035
Robak T., Korycka A., Kasznicki M., Wrzesien-Kus A., Smolewski P., Curr. Cancer Drug Targets, 2005, 5, 421
Balzarini J., Pharm. World Sci., 1994, 16, 113
Stein D. S., Moore K. H., Pharmacotherapy, 2001, 21, 11
de Clercq E., International Journal of Antimicrobial Agents, 2009, 33, 307
de Clercq E., Antivir Res., 2005, 67, 56
Len C., Mackenzie G., Tetraheron, 2006, 62, 9085
de Clercq E., Biochim. Biophys. Acta, 2002, 1587, 258
Barchi J., Karki R. G., Nicklaus M. C., Siddiqui M. A., George C., Mikhailopulo I. A., Marquez V. E., J. Am. Chem. Soc., 2008, 130, 9048
Shaikh I. K., Kumar S., Lundhus L., Bond A. D., Sharma P. K., Nielsen P., J. Org. Chem., 2009, 74, 1557
Zhou C., Chattopadhyaya J., Curr. Opin. Drug. Discov. Devel., 2009, 12, 876
Ewing D. F., Fahmi N. E., Len C., Mackenzie G., Pranzo A., J. Chem. Soc., Perkin Trans. 1, 2000, 3561
Kolb H. C., Finn M. G., Sharpless K. B., Angew. Chem. Int. Ed. Engl., 2001, 40, 2004
Bock V. D., Hiemstra H., Maarseveen J. H., Eur. J. Org. Chem., 2006, 51
Binder W. H., Sachsenhofer R., Macromol. Rapid Commun., 2007, 28, 15
Binder W. H., Sachsenhofer R., Macromol. Rapid Commun., 2008, 29, 952
Alvarez R., Velazquez S., San-Felix A., Aquaro S., de Clercq E., Perno C. F., Karlsson A., Balzarini J., Camarasa M. J., J. Med. Chem., 1994, 37, 4185
Genin M. J., Allwine D. A., Anderson D. J., Barbachyn M. R., Emmert D. E., Garmon S. A., Graber D. R., Grega K. C., Hester J. B., Hutchinson D. K., Morris J., Reischer R. J., Ford C. W., Zurenko G. E., Hamel J. C., Schaadt R. D., Stper D., Yagi B. H., J. Med. Chem., 2000, 43, 953
Lewis W. G., Green L. G., Grynszpan F., Radic Z., Carlier P. R., Taylor P., Finn M. G., Sharpless K. B., Angew. Chem., Int. Ed., 2002, 41, 1053
KolbH. C., Sharpless K. B., Drug Discovery Today, 2003, 8, 1128
Tron G. C., Pirali T., Billington R. A., Canonico P. L., Sorba G., Genazzani A. A., Med. Res. Rev., 2008, 28, 278
Lutz J. F., Zarafshani Z., Adv. Drug. Delivery Rev., 2008, 60, 958
Moorhouse A. D., Moses J. E., Chem. Med. Chem., 2008, 3, 715
de Clercq E., Nature Review Drug Discovery, 2002, 1, 13
Sun J. B., Liu X. Y., Li H. M., Duan R. H., Wu J. C., Hel. Chim. Acta, 2012, 95, 772
Maag H., Rydzewski R. M., McRoberta M. J., Crawford-Ruth D., Verheyden J. P. H., Prisbe E. J., J. Med. Chem., 1992, 35, 1440
Smith D. B., Kalayanov G., Sund C., Winqvist A., Pinho P. O., Maltseva T., Morisson V., Leveque V., Rajyaguru S., Le Pogam S., Najera I., Benkestock K., Zhou X. X., Maag H., Cammack N., Martin J. A., Swallow S., Johansson N. G., Klumpp K., Smith M., J. Med. Chem., 2009, 52, 219
Teste K., Colombeau L., Hadj-Bouazza A., Lucas R., Zerrouki R., Krausza P., Champavier Y., Carbohydrate Research, 2008, 343, 1490
Matsuda A., Yasuoka J., Ueda T., Chem. Pharm. Bull., 1989, 37, 1659
Yu X., Yu Y., Liu B., Luo K., Kong W., Mao P., Yu X. F., Science, 2003, 302, 1056
Kimpton J., Emerman M., J. Virol., 1992, 66, 2232
Tian C., Yu X., Zhang W., Wang T., Xu R., Yu X. F., J. Virol., 2006, 80, 3112
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Sun, Jb., Liu, Rw., Xuan, Ll. et al. Synthesis and anti-HIV activity of Triazolo-fused 3′,4′-cyclic and 4′-spiro nucleoside analogues. Chem. Res. Chin. Univ. 29, 473–476 (2013). https://doi.org/10.1007/s40242-013-2375-5
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DOI: https://doi.org/10.1007/s40242-013-2375-5