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http://dx.doi.org/10.5012/bkcs.2012.33.10.3417

Synthesis and Antiviral Activity of 3-Aminoindole Nucleosides of 2-Acetamido-2-deoxy-D-glucose  

Abdel-Rahman, Adel A.H. (Department of Chemistry, Faculty of Science, Menoufia University)
El-Latif, Mona M. Abd (Dean of Advanced Technology and New Materials Research Institute, City for Scientific Research and Technology Applications)
El-Essawy, Farag A. (Department of Chemistry, Faculty of Science, Menoufia University)
Barakat, Yousif A. (Department of Chemistry, Faculty of Science, Menoufia University)
Publication Information
Abstract
A new method for the construction of 3-aminoindole nucleosides of 2-acetamido-2-deoxy-D-glucose based is presented. Nitration and acetylation of the indole nucleosides by acetic anhydride-nitric acid mixture followed by reduction using silver catalyst (SNSM) impregnated on silica gel, afforded the corresponding amino indole nucleosides. The nucleosides were tested for antiviral activity against hepatitis B virus (HBV) to show different degrees of antiviral activities or inhibitory actions.
Keywords
Nucleosides; Nitroindole; Silver nanoparticles; Antiviral activity;
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1 Coffy, S. Rodds, Chemistry of Carbon Compounds, Aliphatic Compounds 1976, Vol. 1, Part F, p. 483, Elsevier, Amsterdam.
2 Marten, D. W.; Mayer, P. A.; Rodwell, V. W.; Granner, D. K. Harpers, Reviews of Biochemistry; 1985, 20th. ed. Lang Medical Publication, CA p. 150.
3 Strange, R. E.; Powell, J. F. Biochem. J. 1954, 58, 80.
4 Sasaki, T.; Minamoto, K.; Suzuki, T.; Yamashita, S. Tetrahedron 1980, 36, 865.   DOI   ScienceOn
5 Abdel-Rahman, A. A.-H. Pharmazie 2001, 56, 773.
6 Al-Masoudi, N. A.; Pfleiderer, W. Tetrahedron 1993, 49, 7579.   DOI   ScienceOn
7 Al-Masoudi, N. A.; Issa, F. B. Acta Chem. Scand. 1997, 51, 958.   DOI
8 Simakov, S. V.; Velezheva, V. S.; Kozik, T. A.; Ershova, Y. A.; Chernov, V. A.; Suvorov, N. N. Pharm. Chem. J. 1983, 17, 707.   DOI
9 Suvorov, N. N.; Velezheva, V. S.; Yarosh, A. V.; Erofeev, Y. V.; Kozik, T. N. Chem. Heterocycl. Compd. 1975, 11, 959.   DOI
10 Velezheva, V. S.; Gunar, G. N.; Balyakina, M. A.; Suvorov, N. N. Chem. Heterocycl. Compd. 1978, 14, 757.   DOI
11 Przhevalskii, N. M.; Skvortsova, N. S.; Magedov, I. V. Chem. Heterocycl. Compd. 2002, 38, 1055.   DOI   ScienceOn
12 Garcia, E. E.; Benjamin, L.; Fryer, R. I. J. Heterocycl. Chem. 1973, 10, 51.   DOI
13 Abdel-Rahman, A. A.-H.; El-Sayed, W. A.; Abdel-Bary, H. M.; Abdel-Megied, A. E.-S.; Morcy, E. M. I. Monatsh. Chem. 2008, 139, 1095.   DOI
14 Pradhan, N.; Pal, A.; Pal, T. Colloids and Surfaces A 2002, 196, 247.   DOI   ScienceOn
15 Liu, P.; Zhao, M. Applied Surface Sci. 2009, 255, 3989.   DOI   ScienceOn
16 Kiasat, A. R.; Mirzajani, R.; Ataeian, F.; Fallah-Mehrjardi, M. Chinese Chem. Lett. 2010, 21, 1015.   DOI   ScienceOn
17 Horton, D. Methods in Carbohydr. Chem. 1964, Vol. VI, 282.
18 Schwyzer, R.; Kappeler, H. Helv. Chim. Acta 1961, 44, 1991.   DOI
19 Sells, M. A.; Zelent, A. Z.; Shvartsman, M.; Acs, G. J. Virol. 1988, 62, 2836.
20 Korba, B. E.; Gerin, J. L. Antiviral Res. 1992, 19, 55.   DOI   ScienceOn
21 Doong, S. L.; Tsai, C. H.; Chinazi, R. F.; Liotta, D. C.; Cheng, Y. C. Proc. Nat. Acad. Sci. USA 1991, 88, 4895.
22 Fouad, T.; Nielsen, C.; Brunn, L.; Pederson, E. B. Sc. J. Az. Med. Fac. (GIRLS) 1998, 19, 1173.
23 Kundu, S.; Ghosh, S. K.; Mandal, M.; Pal, T. New J. Chem. 2002, 26, 1081.   DOI   ScienceOn
24 Pal, T.; Jana, N. R.; Pal, A.; Creighton, J. A.; Beezer, A. E. J. Indian Chem. Soc. 2000, 77, 34.
25 d'Ischia, M.; Napolitano, A.; Pezzella, A. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008; Vol. 3, Chapter 3.04, p 353.
26 Chang, R.; Marco, D. I.; Kuduk, S. WO Patent 042092/2009, Chem. Abstr. 2009, 150, 374291.
27 Bahekar, R. H.; Jain, M. R.; Goel, A.; Patel, D. N.; Prajapati, V. M.; Gupta, A. A.; Jadav, P. A.; Patel, P. R. Bioorg. Med. Chem. 2007, 15, 3248.   DOI   ScienceOn
28 Kesteleyn, B. R. R.; Raboisson, P. J.-M.; Surleraux, D. L. N. G.; Hache, G. Y. P.; Vendeville, S. M. H.; Peeters, A. A.; Wigerink, P. T. B. P. WO Patent 111047/2005, Chem. Abstr. 2006, 144, 6779.
29 Zhang, Z.; Wang, S.; Wan, S.; Ren, S.; Li, W.; Jiang, T. Carbohydr. Res. 2009, 344, 291.   DOI   ScienceOn
30 Romagnoli, R.; Baraldi, P. G.; Sarkar, T.; Carrion, M. D.; Cara, C. L.; Cruz-Lopez, O.; Preti, D.; Tabrizi, M. A.; Tolomeo, M.; Grimaudo, S.; Di Christina, A.; Zonta, N.; Balzarini, J.; Brancale, A.; Hseih, H.-P.; Hamel, E. J. Med. Chem. 2008, 51, 1464.   DOI   ScienceOn
31 Radl, S.; Hezky', P.; Urbankova, J.; Váchal, P.; Krejci, I. Coll. Czech. Chem. Commun. 2000, 65, 280.   DOI   ScienceOn
32 Jana, N. R.; Sau, T. K.; Pal, T. J. Phys. Chem. B 1999, 103, 115.   DOI   ScienceOn
33 Lehmann, F.; Haile, S.; Axen, E.; Medina, C.; Uppenberg, J.; Svensson, S.; Lundbaeck, T.; Rondahl, L.; Barf, T. Bioorg. Med. Chem. Lett. 2004, 14, 4445.   DOI   ScienceOn
34 Roy, S.; Gribble, G. W. Heterocycles 2006, 70, 51.   DOI
35 Hooper, M. K.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2003, 68, 2861.   DOI   ScienceOn
36 Kundu, S.; Ghosh, S. K.; Mandal, M.; Pal, T. New J. Chem. 2003, 27, 656.   DOI   ScienceOn
37 Jana, N. R.; Pal, T. Langmuir 1999, 15, 3458.   DOI   ScienceOn