Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

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)
  • Received : 2012.02.14
  • Accepted : 2012.06.21
  • Published : 2012.10.20
Download PDF
⟨ Previous Next ⟩

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

References

  1. Kundu, S.; Ghosh, S. K.; Mandal, M.; Pal, T. New J. Chem. 2003, 27, 656. https://doi.org/10.1039/b207428a
  2. Jana, N. R.; Pal, T. Langmuir 1999, 15, 3458. https://doi.org/10.1021/la981512i
  3. Jana, N. R.; Sau, T. K.; Pal, T. J. Phys. Chem. B 1999, 103, 115. https://doi.org/10.1021/jp982731f
  4. Kundu, S.; Ghosh, S. K.; Mandal, M.; Pal, T. New J. Chem. 2002, 26, 1081. https://doi.org/10.1039/b201844f
  5. Pal, T.; Jana, N. R.; Pal, A.; Creighton, J. A.; Beezer, A. E. J. Indian Chem. Soc. 2000, 77, 34.
  6. 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.
  7. Chang, R.; Marco, D. I.; Kuduk, S. WO Patent 042092/2009, Chem. Abstr. 2009, 150, 374291.
  8. 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. https://doi.org/10.1016/j.bmc.2007.02.029
  9. 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.
  10. Zhang, Z.; Wang, S.; Wan, S.; Ren, S.; Li, W.; Jiang, T. Carbohydr. Res. 2009, 344, 291. https://doi.org/10.1016/j.carres.2008.11.015
  11. 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. https://doi.org/10.1021/jm7011547
  12. Radl, S.; Hezky', P.; Urbankova, J.; Váchal, P.; Krejci, I. Coll. Czech. Chem. Commun. 2000, 65, 280. https://doi.org/10.1135/cccc20000280
  13. 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. https://doi.org/10.1016/j.bmcl.2004.06.057
  14. Roy, S.; Gribble, G. W. Heterocycles 2006, 70, 51. https://doi.org/10.3987/COM-06-S(W)8
  15. Hooper, M. K.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2003, 68, 2861. https://doi.org/10.1021/jo0266339
  16. Simakov, S. V.; Velezheva, V. S.; Kozik, T. A.; Ershova, Y. A.; Chernov, V. A.; Suvorov, N. N. Pharm. Chem. J. 1983, 17, 707. https://doi.org/10.1007/BF00765019
  17. Suvorov, N. N.; Velezheva, V. S.; Yarosh, A. V.; Erofeev, Y. V.; Kozik, T. N. Chem. Heterocycl. Compd. 1975, 11, 959. https://doi.org/10.1007/BF00470499
  18. Velezheva, V. S.; Gunar, G. N.; Balyakina, M. A.; Suvorov, N. N. Chem. Heterocycl. Compd. 1978, 14, 757. https://doi.org/10.1007/BF00471645
  19. Przhevalskii, N. M.; Skvortsova, N. S.; Magedov, I. V. Chem. Heterocycl. Compd. 2002, 38, 1055. https://doi.org/10.1023/A:1021244929340
  20. Garcia, E. E.; Benjamin, L.; Fryer, R. I. J. Heterocycl. Chem. 1973, 10, 51. https://doi.org/10.1002/jhet.5570100112
  21. 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. https://doi.org/10.1007/s00706-008-0891-7
  22. Pradhan, N.; Pal, A.; Pal, T. Colloids and Surfaces A 2002, 196, 247. https://doi.org/10.1016/S0927-7757(01)01040-8
  23. Liu, P.; Zhao, M. Applied Surface Sci. 2009, 255, 3989. https://doi.org/10.1016/j.apsusc.2008.10.094
  24. Kiasat, A. R.; Mirzajani, R.; Ataeian, F.; Fallah-Mehrjardi, M. Chinese Chem. Lett. 2010, 21, 1015. https://doi.org/10.1016/j.cclet.2010.05.024
  25. Horton, D. Methods in Carbohydr. Chem. 1964, Vol. VI, 282.
  26. Schwyzer, R.; Kappeler, H. Helv. Chim. Acta 1961, 44, 1991. https://doi.org/10.1002/hlca.19610440723
  27. Sells, M. A.; Zelent, A. Z.; Shvartsman, M.; Acs, G. J. Virol. 1988, 62, 2836.
  28. Korba, B. E.; Gerin, J. L. Antiviral Res. 1992, 19, 55. https://doi.org/10.1016/0166-3542(92)90056-B
  29. Doong, S. L.; Tsai, C. H.; Chinazi, R. F.; Liotta, D. C.; Cheng, Y. C. Proc. Nat. Acad. Sci. USA 1991, 88, 4895.
  30. Fouad, T.; Nielsen, C.; Brunn, L.; Pederson, E. B. Sc. J. Az. Med. Fac. (GIRLS) 1998, 19, 1173.
  31. Coffy, S. Rodds, Chemistry of Carbon Compounds, Aliphatic Compounds 1976, Vol. 1, Part F, p. 483, Elsevier, Amsterdam.
  32. 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.
  33. Strange, R. E.; Powell, J. F. Biochem. J. 1954, 58, 80.
  34. Sasaki, T.; Minamoto, K.; Suzuki, T.; Yamashita, S. Tetrahedron 1980, 36, 865. https://doi.org/10.1016/0040-4020(80)80036-6
  35. Abdel-Rahman, A. A.-H. Pharmazie 2001, 56, 773.
  36. Al-Masoudi, N. A.; Pfleiderer, W. Tetrahedron 1993, 49, 7579. https://doi.org/10.1016/S0040-4020(01)87232-X
  37. Al-Masoudi, N. A.; Issa, F. B. Acta Chem. Scand. 1997, 51, 958. https://doi.org/10.3891/acta.chem.scand.51-0958

Cited by

  1. Keteniminium Salts as Key Intermediates for the Efficient Synthesis of 3‐Amino‐Indoles and ‐Benzofurans vol.103, pp.1, 2012, https://doi.org/10.1002/hlca.201900217