Synthesis and antiviral properties of arabino and ribonucleosides of 1,3-dideazaadenine, 4-nitro-1,3-dideazapurine and diketopiperazine

Nucleosides, Nucleotides and Nucleic Acids

Volumn 23, Issue 12, 2004, Pages 1815-1824

  Sinha, Sarika ^a   Srivastava, Richa ^a   De Clercq, Erik ^b   Singh, Ramendra K ^a  

^a UNIVERSITY OF ALLAHABAD   (India)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Antivirals; Arabinosides; Dideazapurines; Diketopiperazine; Ribosides

Indexed keywords

1 (1 BETA DEXTRO ARABINOFURANOSYL)DIKETOPIPERAZINE; 9 (1 BETA DEXTRO ARABINOFURANOSYL) 1,3 DIDEAZAADENINE; 9 (1 BETA DEXTRO ARABINOFURANOSYL) 4 NITRO 1,3 DIDEAZAPURINE; 9 (1 BETA DEXTRO RIBOFURANOSYL) 1,3 DIDEAZAADENINE; 9 (1 BETA DEXTRO RIBOFURANOSYL) 4 NITRO 1,3 DIDEAZAPURINE; CYTIDINE DEAMINASE; NUCLEOSIDE DERIVATIVE; THYMIDYLATE SYNTHASE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; NONHUMAN; PARAINFLUENZA VIRUS 3; REOVIRUS; STEREOSPECIFICITY; VIRUS REPLICATION;

ADENINE; ANIMALS; ANTIVIRAL AGENTS; ARABINONUCLEOSIDES; CELL LINE; CELL SURVIVAL; CERCOPITHECUS AETHIOPS; DRUG EVALUATION, PRECLINICAL; HELA CELLS; HUMANS; NITRO COMPOUNDS; NUCLEIC ACID CONFORMATION; PIPERAZINES; PURINES; RIBONUCLEOSIDES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS; VIRUSES;

ARA; HUMAN HERPESVIRUS 1; HUMAN HERPESVIRUS 2; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN PARAINFLUENZA VIRUS 3; MAMMALIAN ORTHOREOVIRUS 1; REOVIRUS SP.; SIMPLEXVIRUS;

EID: 10644292508     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-200040614     Document Type: Article

References (46)

1. Robins, R.K.; Revankar, G.R. Design of nucleoside analogs as potential antiviral agents. In Antiviral Drug Development, A Multidisciplinary Approach; Clercq, E.D., Walker, R.T., Eds.; Series A: Life Sicences, Plenum Press: New York, 1988; Vol. 143, 11.
2. Elion, G.B. Science 1989, 244, 41.
3. Elion, G.B.; Hitchings, G.H. Adv. Chemother. 1965, 2, 91.
4. Legraverend, M.; Aubertin, A.M.; Oberg, G.; Huel, C.; Bisagni, E. Synthesis and anti-HIV evaluation of 7-deaza analogues of carbovir. Nucleosides & Nucleotides 1994, 13 (4), 915-923.
5. Elion, G.B. Adv. Enzyme Regul. 1985, 24, 323.
6. Gudmundsson, K.S.; Freeman, G.A.; Drach, J.C.; Townsend, L.B. J. Med. Chem. 2000, 43 (12), 2473.
7. Zackny, V.L.; Gershburg, E.; Davis, M.G.; Biron, K.K.; Pagano, J.S., Jr. J. Virol. 1999, 73 (9), 7271.
8. Underwood, M.R.; Harvey, R.J.; Stanat, S.C.; Hemphill, M.L.; Miller, T.; Drach, J.C.; Townsend, L.B.; Biron, K.K. J. Virol. 1998, 72 (1), 717.
9. Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Nitta, I.; Baba, M.; Shigeta, S.; Walker, R.T.; Clercq, E.D.; Miyasaka, T. J. Med. Chem. 1992, 35, 4713.
10. Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Inouye, N.; Baba, M.; Shigeta, S.; Walker, R.T.; Clercq, E.D.; Miyasaka, T. J. Med. Chem. 1995, 38, 2860.
11. Genini, D.; Adachi, S.; Chao, Q.; Rose, D.W.; Carrera, C.J.; Cottam, H.B.; Carson, D.A.; Leoni, L.M. Blood 2000, 96 (10), 3537.
12. Singh, R.K.; Ohuchi, S.; Wada, T.; Hata, T. Chem. Lett. 1992, 1505.
13. Singh, R.K.; Ohuchi, S.; Wada, T.; Hata, T. Nucleosides Nucleotides 1998, 17, 123.
14. Lee, W.W.; Benitez, A.; Goodman, L.; Baker, B.R. J. Am. Chem. Soc. 1960, 82, 2648.
15. Chien, L.T.; Shabel, F.M.; Alford, C.A., Jr. Arabinosyl nucleosides and nucleotides. In Selective Inhibition of Viral Functions; Carter, W.A., Ed.; CRC Press: Cleveland, OH, 1977; 227.
16. North, T.W.; Cohen, S.S. Pharmacol. Ther. 1979, 4, 81.
17. Muller, W.E.G.; Zahn, R.K.; Bittlingmaier, K.I.; Falke, D. Ann. N. Y. Acad Sci. 1977, 284, 34.
18. Vilde, G.L.; Bricaire, F.; Huchon, A.; Brun-Vezinet, F. J. Med. Virol. 1983, 12, 149.
19. Muler, W.E.G.; Zahn, R.K.; Berger, R.; Falke, D. Virology 1977, 76, 787.
20. Zou, R.; Kawashima, E.; Freeman, G.A.; Koszalka, G.W.; Drach, J.C.; Townsend, L.B. Nucleosides Nucleotides Nucl. Acids 2000, 19 (1-2), 125.
21. Gudmundsson, K.S.; Tidwell, J.; Lippa, N.; Koszalka, G.W.; van Draanen, N.; Ptak, R.G.; Drach, J.C.; Townsend, L.B. J. Med. Chem. 2000, 43 (12), 2464.
22. Townsend, L.B.; Gudmundsson, K.S.; Daluge, S.M.; Chen, J.J.; Zhu, Z.; Koszalka, G.W.; Boyd, L.; Chamberlain, S.D.; Freeman, G.A.; Biron, K.K.; Drach, J.C. Nucleosides Nucleotides 1999, 18 (4-5), 509.
23. Chen, J.J.; Wei, Y.; Drach, J.C.; Townsend, L.B. J. Med. Chem. 2000, 43 (12), 2449.
24. Zhu, Z.; Lippa, B.; Drach, J.C.; Townsend, L.B. J. Med. Chem. 2000, 43 (12), 2430.
25. Krosky, P.M.; Ptak, R.G.; Underwood, M.R.; Biron, K.K.; Townsend, L.B.; Drach, J.C. Antivir. Chem. Chemother. 2000, 11 (5), 349.
26. Krosky, P.M.; Borysko, K.Z.; Nassiri, M.R.; Devivar, R.V.; Ptak, R.G.; Davis, M.G.; Biron, K.K.; Townsend, L.B.; Drach, J.C. Antimicrob. Agents Chemother. 2002, 46 (2), 478.
27. Cristalli, G.; Franchetti, P.; Grifantini, M.; Sauro, V.; Lupidi, G.; Riva, F.; Bordoni, T.; Geroni, C.; Verini, M.A. J. Med. Chem. 1988, 31, 390.
28. Seela, F.; Bourgeois, W. Synthesis 1989, 12, 912.
29. Rousseau, R.J.; Townsend, L.B.; Robins, R.K. Biochemistry 1966, 5, 756.
30. Bodner, J.P.; Cantoni, G.L.; Chiang, R.K. Biochem. Biophys. Res. Commun. 1981, 98, 476.
31. Bader, J.P.; Brown, N.R.; Chiang, R.K.; Cantoni, G.L. Virology 1978, 89, 494.
32. Pugh, C.S.G.; Borchardt, R.T.; Stone, H.O. Biochemistry 1977, 16, 3928.
33. Depelley, J.; Granet, R.; Krausz, P.; Piekarski, S. Nucleosides Nucleotides 1994, 13 (4), 1007.
34. Reefschager, J.; Herrman, G.; Barwolff, D.; Schwarz, B.; Cech, D.; Langen, P. Antivir. Res. 1983, 3, 175.
35. Camiener, G.W. Studies of the enzymatic deamination of aracytidine V. Inhibition in vitro and in vivo by tetrahydrouridine and other reduced pyrimidine nucleosides. Biochem. Pharmacol. 1968, 9, 1981-1991.
36. Prusoff, W. Biochim. Biophys. Acta 1959, 32, 295.
37. McCombie, S.W.; Tagat, R.J.; Vice, S.F.; Lin, S.; Steensma, R.; Palani, A.; Neustadt, B.R.; Baroudy, B.M.; Stizki, J.M.; Endres, M.; Cox, K.; Dan, N.; Chou, C.C. Bioorg. Med. Chem. Lett. 2003, 13 (3), 567.
38. Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488.
39. Vorbrüggen, H.; Bennua, B. Chem. Ber. 1981, 114, 1279.
40. Singh, R.K.; Takaku, H. Nucleosides Nucleotides 1999, 18, 1403.
41. Wright, R.S.; Khorana, H.G. J. Am. Chem. Soc. 1958, 80, 1994.
42. Ness, R.K.; Fletcher, H.G., Jr. J. Am. Chem. Soc. 1958, 80, 2007.
43. Woolley, D.W. J. Biol. Chem. 1944, 152, 225.
44. Vogel, A.I. Some heterocyclic compounds. In Practical Organic Chemistry, 4th Ed.; Longmans, Green & Co. Ltd.: London, 1976; 909.
45. Kotick, M.P.; Szantay, C.; Bardos, T.J. J. Org. Chem. 1969, 34 (12), 3806.
46. Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.; Desmyter, J.; Clercq, E.D. J. Virol. Meth. 1988, 20 (4), 309.