Synthesis and antiviral evaluation of certain novel pyrazinoic acid C- nucleosides

Journal of Medicinal Chemistry

Volumn 41, Issue 8, 1998, Pages 1236-1241

  Walker II, John A ^a   Liu, Weimin ^c   Wise, Dean S ^b   Drach, John C ^d   Townsend, Leroy B ^d  

^a ProtoGene Laboratories Inc   (United States)

^b Berry and Associates Inc   (United States)

^c SHIONOGI AND CO LTD   (Japan)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DICHLORO 6 (BETA RIBOFURANOSYL)PYRAZINE 2 CARBOXYLIC ACID ETHYL ESTER; ANTIVIRUS AGENT; GANCICLOVIR; NUCLEOSIDE DERIVATIVE; PYRAZINOIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HUMAN; HUMAN CELL; HUMAN CYTOMEGALOVIRUS; REACTION ANALYSIS;

ANTIVIRAL AGENTS; CELL DIVISION; CELL SURVIVAL; CYTOMEGALOVIRUS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; ENZYME-LINKED IMMUNOSORBENT ASSAY; FIBROBLASTS; HERPESVIRUS 1, HUMAN; HUMANS; KB CELLS; MICROBIAL SENSITIVITY TESTS; PLAQUE ASSAY; PYRAZINES; RIBOSE; SKIN;

EID: 0032499280     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970532z     Document Type: Article

References (45)

1. For a review on the chemistry and biology of nucleosides, see: (a) Nucleosides as Biological Probes; Suhadolnik, R. J., Ed.; John Wiley & Sons: New York, 1979. (b) Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1988, Vol. 1; 1991, Vol. 2. Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C. K., Baker, D. C., Eds.; Plenum Press: New York, 1993. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3.
2. For a review on the chemistry and biology of nucleosides, see: (a) Nucleosides as Biological Probes; Suhadolnik, R. J., Ed.; John Wiley & Sons: New York, 1979. (b) Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1988, Vol. 1; 1991, Vol. 2. Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C. K., Baker, D. C., Eds.; Plenum Press: New York, 1993. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3.
3. For a review on the chemistry and biology of nucleosides, see: (a) Nucleosides as Biological Probes; Suhadolnik, R. J., Ed.; John Wiley & Sons: New York, 1979. (b) Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1988, Vol. 1; 1991, Vol. 2. Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C. K., Baker, D. C., Eds.; Plenum Press: New York, 1993. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3.
4. For a review on the chemistry and biology of nucleosides, see: (a) Nucleosides as Biological Probes; Suhadolnik, R. J., Ed.; John Wiley & Sons: New York, 1979. (b) Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1988, Vol. 1; 1991, Vol. 2. Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C. K., Baker, D. C., Eds.; Plenum Press: New York, 1993. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3.
5. For a review on the chemistry and biology of nucleosides, see: (a) Nucleosides as Biological Probes; Suhadolnik, R. J., Ed.; John Wiley & Sons: New York, 1979. (b) Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1988, Vol. 1; 1991, Vol. 2. Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C. K., Baker, D. C., Eds.; Plenum Press: New York, 1993. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3.
6. For a review of the chemistry and biology of C-glycosides, see: (a) Watanabe, K. A. The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, Chapter 5. (b) Hacksell, U.; Daves, G. D., Jr. The Chemistry and Biochemistry of C-Nucleosides and C-Arylglycosides. Prog. Med. Chem. 1985, 22, 1-65. Buchanan, J. G. The C-Nucleoside Antibiotics. Prog. Chem. Org. Nat. Prod. 1983, 44, 243-299. Goodchild, J. The Biochemistry of Nucleoside Antibiotics. Top. Antibiot. Chem. 1982, 6, 99-227.
7. For a review of the chemistry and biology of C-glycosides, see: (a) Watanabe, K. A. The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, Chapter 5. (b) Hacksell, U.; Daves, G. D., Jr. The Chemistry and Biochemistry of C-Nucleosides and C-Arylglycosides. Prog. Med. Chem. 1985, 22, 1-65. Buchanan, J. G. The C-Nucleoside Antibiotics. Prog. Chem. Org. Nat. Prod. 1983, 44, 243-299. Goodchild, J. The Biochemistry of Nucleoside Antibiotics. Top. Antibiot. Chem. 1982, 6, 99-227.
8. For a review of the chemistry and biology of C-glycosides, see: (a) Watanabe, K. A. The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, Chapter 5. (b) Hacksell, U.; Daves, G. D., Jr. The Chemistry and Biochemistry of C-Nucleosides and C-Arylglycosides. Prog. Med. Chem. 1985, 22, 1-65. Buchanan, J. G. The C-Nucleoside Antibiotics. Prog. Chem. Org. Nat. Prod. 1983, 44, 243-299. Goodchild, J. The Biochemistry of Nucleoside Antibiotics. Top. Antibiot. Chem. 1982, 6, 99-227.
9. For a review of the chemistry and biology of C-glycosides, see: (a) Watanabe, K. A. The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, Chapter 5. (b) Hacksell, U.; Daves, G. D., Jr. The Chemistry and Biochemistry of C-Nucleosides and C-Arylglycosides. Prog. Med. Chem. 1985, 22, 1-65. Buchanan, J. G. The C-Nucleoside Antibiotics. Prog. Chem. Org. Nat. Prod. 1983, 44, 243-299. Goodchild, J. The Biochemistry of Nucleoside Antibiotics. Top. Antibiot. Chem. 1982, 6, 99-227.
10. (a) Mizuno, K.; Tsujino, M.; Takeda, M.; Hayashi, M.; Atsumi, K.; Asano, K.; Matsuda, T. Studies on Bredinin. I. Isolation, Characterization, and Biological Properties. J. Antibiot. 1974, 27, 775-782.
11. (b) Amemiya, H.; Itoh, H. Mizoribine (Bredinin®): Mode of Action and Effects on Graft Rejection. In Immunosupressive Drugs. Developments in Anti-Rejection Therapy; Thomson, A. W., Starzl, T. E., Eds.; Edward Arnold: London, 1994; pp 161-176.
12. (a) Konno, K.; Hayano, K.; Shirahama, H.; Saito, H.; Matsumoto, T. Structure and Synthesis of Clitidine, a New Pyridine Nucleoside from Clitocybe acromelalga. Tetrahedron Lett. 1977, 481-482.
13. (b) Konno, K.; Hayano, K.; Shirahama, H.; Saito, H.; Matsumoto, T. Clitidine. A New Toxic Pyridine Nucleoside from Clitocybe acromelalga. Tetrahedron 1982, 38, 3281-3284.
14. (a) Gerzon, K.; Williams, R. H.; Hoehn, M.; Gorman, M.; DeLong, D. C. Pyrazomycin, A C-Nucleoside with Antiviral Activity. Presented at the Second International Congress on Heterocyclic Chemistry, Montpellier, France, July 1969; Abstract C-30.
15. (b) Williams, R. H.; Hoehn, M. U.S. Patent 3,802,999, 1974.
16. Sweeney, M. J.; Davis, F. A.; Gutowski, G. E.; Hamill, R. L.; Hoffman, D. H.; Poore, G. A. Experimental Antitumor Activity of Pyrazomycin. Cancer Res. 1973, 33, 2619-2623.
17. Gutowski, G. E.; Sweeney, M. J.; DeLong, D. C.; Hamill, R. L.; Gerzon, K.; Dyke, R. W. Biochemistry and Biological Effects of the Pyrazofurins (Pyrazomycins): Initial Clinical Trial. Ann. N. Y. Acad. Sci. 1975, 255, 544-551.
18. Witkowski, J. T.; Robins, R. K.; Sidwell, R. W.; Simon, L. N. Design, Synthesis, and Broad-Spectrum Antiviral Activity of 1-β-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide and Related Nucleosides. J. Med. Chem. 1972, 15, 1150-1154.
19. (a) Fuertes, M.; Garcia-Lopez, T.; Garcia-Munoz, G.; Stud, M. Synthesis of C-Glycosyl Thiazoles. J. Org. Chem. 1976, 41, 4074-4077.
20. (b) Srivastava, P. C.; Pickering, M. V.; Allen, L. B.; Streeter, D. G.; Campbell, M. T.; Witowski, J. T.; Sidwell, R. W.; Robins, R. K. Synthesis and Antiviral Activity of Certain Thiazole C-Nucleosides. J. Med. Chem. 1977, 20, 256-262.
21. Srivastava, P. C.; Robins, R. K. Synthesis and Antitumor Activity of 2-β-D-Ribofuranosylselenazole-4-carboxamide and Related Derivatives. J. Med. Chem. 1983, 26, 445-448.
22. (a) Tricot, G.; Jayaram, H. N.; Weber, G.; Hoffman, R. Tiazofurin: Biological and Clinical Uses. Int. J. Cell Cloning 1990, 8, 161-170.
23. (b) Robins, R. K.; Finch, R. A.; A very, T. L. Nucleoside and Nucleotide Modulation of Oncogenic Expression: A New Approach to Cancer Chemotherapy. In Anticancer Drug Discovery and Developments: Natural Products and New Molecular Models; Valeriote, F. A., Corbett, T. H., Baker, L. H., Eds.; Kluwer Academic Publishers; Boston, 1994; pp 149-182.
24. (a) Krohn, K.; Heins, H.; Wielckens, K. Synthesis and Cytotoxic Activity of C-Glycosidic Nicotinamide Riboside Analogues. J. Med. Chem. 1992, 35, 511-517.
25. (b) Jayaram, H. N.; Gharehbaghi, K.; Jayaram, N. H.; Rieser, J.; Krohn, K.; Paull, K. D. Cytotoxicity of a New IMP Dehydrogenase Inhibitor, Benzamide Riboside, to Human Myelogenous Leukemia K562 Cells. Biochem. Biophys. Res. Commun. 1992, 186, 1600-1606.
26. (a) Voegel, J. J.; Benner, S. A. Synthesis and Characterization of Non-Standard Nucleosides and Nucleotides Bearing the Acceptor-Donor-Donor Pyrimidine Analog 6-Amino-3-methylpyrazin-2(1H)-one. Helv. Chim. Acta 1996, 79, 1863-1880 and references therein,
27. (b) von Krosigk, U.; Benner, S. A. pH-Independent Triple Helix Formation by an Oligonucleotide Containing a Pyrazine Donor-Donor-Acceptor Base. J. Am. Chem. Soc. 1995, 117, 5361-5362.
28. (a) Chen, J. J.; Walker, J. A., II; Liu, W.; Wise, D. S.; Townsend, L. B. An Efficient and Stereospecific Synthesis of Novel Pyrazine C-Nucleosides. Tetrahedron Lett. 1995, 36, 8363-8366.
29. (b) Liu, W.; Walker, J. A., II; Chen, J. J.; Wise, D. S.; Townsend, L. B. Synthesis of Pyrazine C-Ribosides via Direct Metalation. Tetrahedron Lett. 1996, 37, 5325-5328.
30. Liu, W.; Walker, J. A., II; Chen, J. J.; Wise, D. S.; Townsend, L. B. A Short and Efficient Synthesis of Some Novel Pyrazine C-Nucleosides. Presented at the 211th National Meeting of the American Chemical Society, New Orleans, LA, March 1996; Paper ORGN 265.
31. Turck, A.; Mojovic, L.; Quéguiner, G. A New Route to 2,3-Disubstituted Pyrazines; Regioselective Metalation of Chloropyrazine. Synthesis 1988, 11, 881-884.
32. Wakefield, B. J. Organolithium Methods; Academic Press, Inc: San Diego, CA, 1988.
33. Unpublished results.
34. Parker, K. A.; Gibbons, E. G. A Direct Synthesis of Primary Amides from Grignard Reagents. Tertrahedron Lett. 1975, 16, 981-984.
35. For reviews of CSI, see: (a) Rasmussen, J. K.; Hassner, A. Recent Developments in the Synthetic Uses of Chlorosulfonyl Isocyanate. Chem. Rev. 1976, 76, 389-408. (b) Dhar, D. N.; Murthy, K. S. K. Recent Advances in the Chemistry of Chlorosulfonyl Isocyanate. Synthesis 1986, 437-449.
36. For reviews of CSI, see: (a) Rasmussen, J. K.; Hassner, A. Recent Developments in the Synthetic Uses of Chlorosulfonyl Isocyanate. Chem. Rev. 1976, 76, 389-408. (b) Dhar, D. N.; Murthy, K. S. K. Recent Advances in the Chemistry of Chlorosulfonyl Isocyanate. Synthesis 1986, 437-449.
37. Chakraborty, D. P.; Mandal, A. K.; Roy, S. K. Ethyl Carbamate as an Aminocarbonylating Agent: Modification of Gattermann's Amidation Reaction. Synthesis 1981, 977-979.
38. Mander, L. N.; Sethi, S. P. Regioselective Synthesis of β-Ketoesters from Lithium Enolates and Methyl Cyanoformate. Tetrahedron Lett. 1983, 24, 5425-5428.
39. Rbo, T.; Abuh, Y. F. One-Pot Synthesis of Pyrimidine-5-carboxaldehyde and Ethyl Pyrimidine-5-carboxylate by Utilizing Pyrimidin-5-yl-lithium. Synth. Commun. 1994, 24, 253-256.
40. See the Supporting Information for details of the X-ray structural determination of compound 5.
41. Still, W. C.; Kahn, M.; Mitra, A. A Rapid Chromatographic Technique for Preparative Separations with Moderate Resolution. J. Org. Chem. 1978, 43, 2923-2925.
42. Turk, S. R.; Shipman, C., Jr.; Nassiri, M. R.; Genzingler, G.; Krawczyk, S. H.; Townsend, L. B.; Drach, J. C. Pyrrolo[2,3-d]pyrimidine Nucleosides as Inhibitors of Human Cytomegalovirus. Antimicrob. Agents Chemother. 1987, 31, 544-550.
43. Prichard, M. N.; Turk, S. R.; Coleman, L. A.; Engelhardt, S. L.; Shipman, C., Jr.; Drach, J. C. A Microtiter Virus Yield Reduction Assay for The Evaluation of Antiviral Compounds Against Human Cytomegalovirus and Herpes Simplex Virus. J. Virol. Methods 1990, 28, 101-106.
44. Prichard, M. N.; Shipman, C., Jr. A Three-Dimensional Model To Analyze Drug-Drug Interactions. Antiviral Res. 1990, 14, 181-206.
45. Prichard, M. N.; Prichard, L. E.; Baguley, W. A.; Nassiri, M. R.; Shipman, C., Jr. Three-Dimensional Analysis of the Synergistic Cytotoxicity of Ganciclovir and Zidovudine. Antimicrob. Agents Chemother. 1991, 35, 1060-1065.