Anti-Hepatitis B Virus Activity of New N4-β-D-Glycoside Pyrazolo[3,4-d]pyrimidine Derivatives

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 64, Issue 5-6, 2009, Pages 323-328

  El Sayed, Wael A ^a   Ramiz, Mahmoud M M ^b   Abdel Rahman, Adel A H ^c  

^a NATIONAL RESEARCH CENTRE   (Egypt)

^b MENOUFIA UNIVERSITY   (Egypt)

^c MENOUFIA UNIVERSITY   (Egypt)

Author keywords

Anti Hepatitis B Virus; N Glycosides; Pyrazolo 3,4 d pyrimidines

Indexed keywords

ANTIVIRUS AGENT; GLYCOSIDE; PYRAZOLE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ACETYLATION; ACYLATION; ARTICLE; DRUG EFFECT; HEPATITIS B; HEPATITIS B VIRUS; MICROBIOLOGICAL EXAMINATION; VIRUS REPLICATION;

ACETYLATION; ACYLATION; ANTIVIRAL AGENTS; GLYCOSIDES; HEPATITIS B; HEPATITIS B VIRUS; MICROBIAL SENSITIVITY TESTS; PYRAZOLES; PYRIMIDINES; VIRUS REPLICATION;

HEPATITIS B VIRUS;

EID: 70349337902     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.1515/znc-2009-5-603     Document Type: Article

References (30)

1. Abdel-Megeed M. F., Saleh M. A., Abdo M. A., and El-Hiti G. A. (1995), Reaction of 6-substituted 3-amino-2-phenyl-4 (3H)-quinazolinones with D-ribose and L-arabinose. Collect. Czech. Chem. Commun. 60, 1016-1025.
2. Abdou M. I., Saleh A. M., and Zohdi H. F. (2004), Synthesis and antitumor activity of 5-trifl uoromethyl-2, 4-dihydropyrazol-3-one nucleosides. Molecules 9, 109-116.
3. Ali I. A., Ali O. M., and Abdel-Rahman A. A. H. (2007a), Amino acid derivatives, IV [1]: synthesis and antiviral evaluation of new a-amino acid esters bearing methyl β-D-ribofuranoside side chain. Monatsh. Chem. 138, 909-915.
4. Ali O. M., Amer H. H., and Abdel-Rahman A. A. -H. (2007b), Synthesis of N4-β-D-glycoside cytosines and sugar N4-acetylcytosin-1-ylmethylhydrazones as antiviral agents. J. Chem. Res., 281-283.
5. Al-Saadi M. S., Rostom S. A. F., and Faidallah H. M. (2008), 3-Methyl-2-(4-substituted phenyl)-4, 5-dihydronaphtho[1, 2-c]-pyrazoles: Synthesis and in-vitro biological evaluation as antitumour agents. Arch. Pharm. Chem. Life Sci. 341, 181-190.
6. Anderson J. D., Cottam H. B., Larson S. B., Nord L. D., Revankar G. R., and Robins R. K. (1990), Synthesis of certain pyrazolo[3, 4-d]pyrimidin-3-one nucle-osides. J. Heterocycl. Chem. 27, 439-453.
7. Capdeville R., Buchdunger E., Zimmermann J., and Matter A. (2002), Glivec (STI571, imatinib), a rationally developed, targeted anticancer drug. Nat. Rev. Drug Disc. 1, 493-502.
8. Cascieri M. A., Mumford R. A., and Katzen H. M. (1979), The role of H2O2 formation in the insulin-like and insulin antagonistic effects on fat cells of omega-aminoalkyl glycosides. Arch. Biochem. Biophys. 195, 30-44.
9. Danishefsky S. J. and Allen J. R. (2000), From the laboratory to the clinic: A retrospective on fully synthetic carbohydrate-based anticancer vaccines. Angew. Chem. Int. Ed. 39, 836-863.
10. Davies L. P., Brown D. J., Chow S. C., and Johnston G. A. R. (1983), Pyrazolo[3, 4-d]pyrimidines, a new class of adenosine antagonists. Neurosci. Lett. 41, 189-193.
11. Davies L. P., Chow S. C., Skerritt J. H., Brown D. J., and Johnston G. A. R. (1984), Pyrazolo[3, 4-d]pyrimidines as adenosine antagonists. Life Sci. 34, 2117-2128.
12. Durette P. L., Bugianesi R. L., Ponpipom M. M., Shen T. Y., Cascieri M. A., Glitzer M. S., and Katzen H. M. (1978), Structure-activity relationships of aminoalkyl and-aryl glycosides having insulin-like activity. J. Med. Chem. 21, 854-859.
13. Ellis G. P. and Honeyman J. (1955), Glycosylamines. Adv. Carbohydr. Chem. 10, 95-168.
14. El-Sayed W. A., Fathi N. M., Gad W. A., and El-Ashry E. S. H. (2008), Synthesis and antiviral evaluation of some 5-N-arylaminomethyl-2-glycosylsulphanyl-1, 3, 4-oxadiazoles and their analogs against hepatitis A and herpes simplex viruses. J. Carbohydr. Chem. 27, 357-372.
15. Fouad T., Nielsen C., Brunn L., and Pederson E. B. (1998), Use of standardization cell culture assay to assess activities of some potent anti-HIV nucleoside analogues against hepatitis B virus replication. Sc. J. Az. Med. Fac. (GIRLS) 19, 1173-1187.
16. Gadhachanda V. R., Wu B., Wang Z., Kuhen K. L., Cald-well J., Zondler H., Walter H., Havenhand M., and He Y. (2007), 4-Aminopyrimidines as novel HIV-1 inhibitors. Bioorg. Med. Chem. Lett. 17, 260-265.
17. Ghorab M. M., Ismail Z. H., Abdel-Gawad S. M., and Abdel Aziem A. (2004), Antimicrobial activity of amino acid, imidazole, and sulfonamide derivatives of pyrazolo[3, 4-d]pyrimidine. Heteroatom Chem. 15, 57-62.
18. Gorin P. and Mazurek M. (1975), Further studies on the assignment of signals in 13C magnetic resonance spectra of aldoses and derived methyl glycosides. Can. J. Chem. 53, 1212-1223.
19. Holla B. S., Mahalinga M., Karthikeyan M. S., Akber-alib P. M., and Shetty N. S. (2006), Synthesis of some novel pyrazolo[3, 4-d]pyrimidine derivatives as potential antimicrobial agents. Bioorg. Med. Chem. 14, 2040-2047.
20. Hughes R. C. (1973), Glycoproteins as components of cellular membranes. Prog. Biophys. Mol. Biol. 26, 189-268.
21. Julino M. and Stevens M. F. G. (1998), Antitumour polycyclic acridines. Part 5. Synthesis of 7H-pyrido[4, 3, 2-kl]acridines with exploitable functionality in the pyridine ring. J. Chem. Soc. Perkin Trans. 1, 1677-1684.
22. Katzen H. M. (1979), Carbohydrate inhibitors of con-canavalin A that inhibit binding of insulin-sepharose to fat cells and antagonize and mimic insulin's bioactivity. A possible role for membrane carbohydrate in insulin's action. J. Biol. Chem. 254, 2983-2992.
23. Kent P. W. (1967), Structure and function of glycoproteins. Essays Biochem. 3, 105-151.
24. Korba B. E. and Gerin J. L. (1992), Use of a standardized cell culture assay to assess activities of nu-cleoside analogs against hepatitis B virus replication. Antiviral Res. 19, 55-70.
25. Kuhn R. (1957), Aminozucker. Angew. Chem. 69, 23-33.
26. Ojala W. H., Ostman J. M., and Ojala C. R. (2000), Schiff bases or glycosylamines: crystal and molecular structures of four derivatives of D-mannose. Carbohydr. Res. 326, 104-112.
27. Pfleiderer W. and Schündehütte K. H. (1958), Untersuchungen in der Pyrimidinreihe IV. Umsetzungen mit 1, 3-dimethyl-4-chlorouracil. Liebigs Ann. Chem. 612, 158-163.
28. Rashad A. E., Hegab M. I., Abdel-Megeid R. E., Micky J. A., and Abdel-Megeid F. M. E. (2008), Synthesis and antiviral evaluation of some new pyrazole and fused pyrazolopyrimidine derivatives. Bioorg. Med. Chem. 16, 7102-7106.
29. Sells M. A., Chen M. L., and Acs G. (1987), Production of hepatitis B virus particles in HepG2 cells trans-fected with cloned hepatitis B virus DNA. Proc. Natl. Acad. Sci. USA 84, 1005-1009.
30. Taylor E. C., Patel H., and Kumar H. (1992), Synthesis of pyrazolo 3, 4-d-pyrimidine analogues of the potent agent N-4, 2, 2-amino-4, 3H-oxo-7H-pyrrolo[2, 3-d]py-rimidin-5-ylethylbenzoyl-L-glutamic acid (LY231514). Tetrahedron 48, 8089-8100.