A pair of new anticancer nucleosides based on 1,2,4-triazole
nucleosides and 1-((2-hydroxyethoxy) methyl)-5-(phenylthio)-1H-1,2,4-triazole-3-carboxamide
have been synthesized, and have given the corresponding products in excellent
yields. Its structures and conformations were confirmed by single crystal X-ray
diffraction.
References
[1]
Claire, S. (2001) Nucleoside Mimetics: Their Chemistry and Biological Properties (Advanced Chemistry Texts). Gordon and Beach Science, UK.
[2]
Herdewijn, P., Ed. (2008) Modified Nucleosides in Biochemistry, Biotechnology and Medicine. Wiley-VCH, Weinheim.
http://dx.doi.org/10.1002/9783527623112
[3]
Xia, Y., Liu, Y., Wan, J.Q., Wang, M.H., Rocchi, P., Qu, F.Q., Iovanna, J.L. and Peng, L. (2009) Novel Triazole Ribonucleoside Down-Regulates Heat Shock Protein 27 and Induces Potent Anticancer Activity on Drug-Resistant Pancreatic Cancer. Journal of Medicinal Chemistry, 52, 6083-6096. http://dx.doi.org/10.1021/jm900960v
[4]
Wan, J.Q., Xia, Y., Liu, Y., Wang, M.H., Rocchi, P., Yao, J.H., Qu, F.Q., Neyts, J., Iovanna, J.L. and Peng, L. (2009) Discovery of Novel Arylethynyltriazole Ribonucleosides with Selective and Effective Antiviral and Antiproliferative Activity. Journal of Medicinal Chemistry, 52, 1144-1155.
http://dx.doi.org/10.1021/jm800927r
[5]
Rivera, F., López-Tarruella, S., Vega-Villegas, M.E. and Salcedo, M. (2009) Treatment of Advanced Pancreatic Cancer: From Gemcitabine Single Agent to Combinations and Targeted Therapy. Cancer Treatment Review, 35, 335-339.
http://dx.doi.org/10.1016/j.ctrv.2008.11.007
[6]
Pierantoni, C., Pagliacci, A., Scartozzi, M., Berardi, R., Bianconi, M. and Cascinu, S. (2008) Pancreatic Cancer: Progress in Cancer Therapy. Critical Reviews in Oncology/Hematology, 67, 27-38.
http://dx.doi.org/10.1016/j.critrevonc.2008.01.009
[7]
Wong, H.H. and Lemoine, N.R. (2009) Pancreatic Cancer: Molecular Pathogenesis and New Therapeutic Targets. Nature Reviews Gastroenterology and Hepatology, 6, 412-422. http://dx.doi.org/10.1038/nrgastro.2009.89
[8]
Liu, Y., Xia, Y., Li, W., Maggiani, A., Leyssen, P., Qu, F.Q., Neyts, J. and Peng, L. (2010) S-Aryltriazole Acyclonuc-leosides: Synthesis and Biological Evaluation against Hepatitis C Virus. Bioorganic & Medicinal Chemistry Letters, 20, 3610-3613.
http://dx.doi.org/10.1016/j.bmcl.2010.04.115
[9]
Narik, S.R., Witkowski, J.T. and Robins, R.K. (1974) Synthesis of Nucleosides of 5-Substituted-1,2,4-triazole-3-carboxamides. Journal of Heterocyclic Chemistry, 11, 57-61. http://dx.doi.org/10.1002/jhet.5570110112