Abstract
Synthesis of anti-HIV nucleoside lipophilic derivatives with diol compounds in which two antiviral pharmacophore residues are linked by a single hydrophobic fragment is described. It is suggested to use 2,3,4,5-tetra-O-benzyl-D, L-iditol and 1,12-dodecanediol as hydrophobic transport systems. Succinic and phosphodiester fragments were used for binding molecular units in the target conjugates.
Similar content being viewed by others
References
P. Huang, D. Farquhar, and W. Plunkett, J. Biol. Chem., 265(20), 11914–11918 (1990).
D. M. Huryn and M. Okabe, Chem. Rev., 92(8), 1745–1768 (1992).
E. De Clercq, J. Med. Chem., 38(14), 2491–2517 (1995).
K. Parang, L. I. Wiebe, and E. E. Knaus, J. Pharm. Pharm. Sci., 1(3), 108–114 (1998).
K. Parang, L. Weibe, and E. E. Knaus, J. Cur. Med. Chem., 7(10), 995–1039 (2000).
H. Mitsuya and S. Broder, Nature, 325, 773 (1987).
K. Y. Hostetler, L. M. Stuhmiller, H. B. M. Lenting, et al., J. Biol. Chem., 265(11), 6112–6117 (1990).
C. McGuigan, R. N. Pathirana, N. Mahmood, et al., Antivir. Res., 17(4), 311–321 (1992).
E. T. Hall, J.-P. Yan, P. Melancon, et al., J. Biol. Chem., 269(20), 14355–14358 (1994).
D. Bonnaffe, B. Dupraz, J. Ughetto-Monfrin, et al., J. Org. Chem., 61(3), 895–902 (1996).
C. Meier, M. Lorey, E. De Clerq, et al., J. Med. Chem., 41(9), 1417–1427 (1998).
M. H. St. Clair, J. L. Martin, G. Tudor-Williams, et al., Science, 253, 1557–1559 (1991).
T. Kawaguchi, T. Endoh, T. Seki, et al., J. Pharm. Sci., 80, 404–405 (1991).
J. M. Bailey, K. A. Nelson, M. Lightfoote, et al., Biochem. Soc. Trans., 26(4), S390 (1998).
T. Seki, T. Kawaguchi, and K. Juni, Pharm. Res., 7, 948–952 (1990).
A. Q. Siddiqui, C. Ballatore, C. McGuigan, et al., J. Med. Chem., 42(20), 4122–4128 (1999).
A. Q. Siddiqui, C. Ballatore, C. McGuigan, et al., J. Med. Chem., 42(3), 393–399 (1999).
J. Dessolin, P. Galea, P. Vlieghe, et al., J. Med. Chem., 42(2), 229–241 (1999).
H. Schott, P. S. Ludwig, A. Immelmann, et al., Eur. J. Med. Chem., 34(4), 343–352 (1999).
S. T. Jan, M. J. Shin, T. K. Venkatachalam, et al., Antivir. Chem. Chemother., 10(1), 39–46 (1999).
G. L. Kucera, C. L. Goff, N. Iyer, et al., Antivir. Res., 50(2), 129–137 (2001).
T. Mavromoustakos, T. Calogeropoulou, M. Koufaki, et al., J. Med. Chem., 44(11), 1702–1709 (2001).
H. Matsumoto, T. Kimura, T. Hamawaki, et al., Bioorg. Med. Chem., 9(6), 1589–1600 (2001).
E. M. Orekhova, I. N. Gracheva, B. A. Klyashchitskii, et al., Zh. Org. Khim., 29(11), 1754–1757 (1993).
P. Buchwald and N. Bodor, Pharmazie., 57(2), 87–93 (2002).
N. M. Mahfouz and M. A. Hassan, J. Pharm. Pharmacol., 53(6), 841–848 (2001).
J. Takata, Y. Karube, Y. Nagata, et al., J. Pharm. Sci., 84, 96–100 (1995).
Yu. V. Berezovskaya, M. V. Chudinov, Yu. G. Kirillova, et al., Nucleosides & Nucleotides., 17, 2127–2133 (1998).
R. J. Jones and N. Bischofberger, Antiviral Res., 27(1, 2), 1–17 (1995).
Author information
Authors and Affiliations
Additional information
__________
Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 40, No. 5, pp. 41–45, May, 2006.
Rights and permissions
About this article
Cite this article
Tuchnaya, O.A., Elizarova, S.N., Sharikova, S.A. et al. Synthesis of anti-HIV nucleoside conjugates with lipophilic diol compounds. Pharm Chem J 40, 276–280 (2006). https://doi.org/10.1007/s11094-006-0108-5
Received:
Issue Date:
DOI: https://doi.org/10.1007/s11094-006-0108-5