Synthesis and anti-influenza virus activity of novel pyrimidine derivatives

Antiviral Research

Volumn 42, Issue 2, 1999, Pages 121-137

  Hisaki, M ^a   Imabori, H ^a   Azuma, M ^b   Suzutani, T ^b   Iwakura, F ^a   Ohta, Y ^a   Kawanishi, K ^a   Ichigobara, Y ^a   Node, M ^c   Nishide, K ^c   Yoshida, I ^b   Ogasawara, M ^b  

^a Azwell Inc   (Japan)

^b ASAHIKAWA MEDICAL COLLEGE   (Japan)

^c KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Anti influenza agents; Cytomegalovirus; Herpes simplex virus types 1 and 2; Influenza viruses A and B; Pyrimidine derivatives; Structure antiviral activity relationships

Indexed keywords

ANTIVIRUS AGENT; CYCLOBUTANE DERIVATIVE; PYRIMIDINE DERIVATIVE; RIBAVIRIN;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CELL PROLIFERATION; CELL STRAIN; CONTROLLED STUDY; CYTOMEGALOVIRUS; CYTOTOXICITY; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; INFLUENZA VIRUS A; INFLUENZA VIRUS B; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE; HUMANS; INHIBITORY CONCENTRATION 50; MICROBIAL SENSITIVITY TESTS; ORTHOMYXOVIRIDAE; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

CYTOMEGALOVIRUS; HERPES; INFLUENZA VIRUS; SIMPLEXVIRUS;

EID: 0032898274     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-3542(99)00019-4     Document Type: Article

References (34)

1. Bisacchi G.S., Braitman A., Cianci C.W., Clark J.M., Field A.K., Hagen M.E., Hockstein D.R., Malley M.F., Mitt T., Slusarchyk W.A., Sundeen J.E., Terry B.J., Tuomari A.V., Weaver E.R., Young M.G., Zahler R. Synthesis and antiviral activity of enantiomeric forms of cyclobutyl nucleoside analogues. J. Med. Chem. 34:1991;1415-1421.
2. Boumchita H., Legraverend M., Huel C., Bisagni E. New cyclobutyl analogs of adenosine and guanosine. Part 1. Synthesis of the 9-[3,3-bis(hydroxymethyl)cyclobutyl]purine nucleoside analogs. J. Heterocycl. Chem. 27:1990;1815-1819.
3. Boumchita H., Legraverend M., Guilhem J., Bisagni E. Synthesis of carbocyclic oxetanocin analogues as potential anti-HIV agents. Part 3. Heterocycles. 32:1991;867-871.
4. Cox N.J., Brammer T.L., Regnery H.L. Influenza: Global surveillance for epidemic and pandemic variants. Eur. J. Epidemiol. 10:1994;467-470.
5. Ghendon Y. Influenza vaccines: A main problem in control of pandemics. Eur. J. Epidemiol. 10:1994;485-486.
6. Gravenstein S., Drinka P., Duthie E.H., Miller B.A., Brown C.S., Hensley M., Circo R., Langer E., Ershler W.B. Efficacy of an influenza hemagglutinin-diphtheria toxoid conjugate vaccine in elderly nursing home subjects during an influenza outbreak. J. Am. Geriatr. Soc. 42:1994;245-251.
7. Hayden F.G., Belshe R.B., Clover R.D., Hay A.G., Oakes M.G., Soo W. Emergence and apparent transmission of rimantadine-resistant influenza A virus in families. New Engl. J. Med. 321:1989;1696-1702.
8. Ichikawa Y., Narita A., Shiozawa A., Hayashi Y., Narasaka K. Enantio- and diastereo-selective synthesis of carbocyclic oxetanocin analogues. J. Chem. Soc. Chem. Commun. 24:1989;1919-1921.
9. Jedrzejas M.J., Singh S., Brouillette W.J., Laver W.G., Air G.M., Luo M. Structures of aromatic inhibitors of influenza virus neuraminidase. Biochemistry. 34:1995;3144-3151.
10. Kim C.U., Lew W., Williams M.A., Liu H., Zhang L., Swaminathan S., Bischofberger N., Chen M.S., Mendel D.B., Tai C.Y., Laver W.G., Stevens R.C. Influenza neuraminidase inhibitors possessing a novel hydrophobic interaction in the enzyme active site: Design, synthesis, and structural analysis of carbocyclic sialic acid analogues with potent anti-influenza activity. J. Am. Chem. Soc. 119:1997;681-690.
11. Kurihara T., Sakamoto Y., Kimura T., Ohishi H., Harusawa S., Yoneda R., Suzutani T., Azuma M. Meisenheimer rearrangement of azetopyridoindoles. VIII. Synthesis and antiviral activities of 12-carbaeudistomin analogs. Chem. Pharm. Bull. 44:1996;900-908.
12. LaForce F.M., Nichol K.L., Cox N.J. Influenza: virology, epidemiology, disease, and prevention. Am. J. Prev. Med. 10:1994;31-44.
13. Lamb R.A., Choppin P.W. The gene structure and replication of influenza virus. Annu. Rev. Biochem. 52:1983;467-506.
14. Legraverend M., Boumchita H., Bisagni E. Synthesis of 9-(hexane-1,6-diol-3-yl)purines, a novel series of acyclic nucleoside analogs and antiviral evaluation. J. Heterocycl. Chem. 27:1990;1801-1804.
15. Mengel, R., Schroeder, L., Stransky, W., Linden, G., Schneider, G., Lust, S., 1984. Pyrimidine derivatives. Ger. Offen. DE. 3,305,524.
16. Mengel, R., Schroeder, L., Stransky, W., Linden, G., Schneider, G., 1988. Preparation of 2,6-diaminopyrimidines as herbicides and agrochemical microbicides. Ger. Offen. DE. 3,717,480.
17. Monto A.S., Arden N.H. Implications of viral resistance to amantadine in control of influenza A. Clin. Infect. Dis. 15:1992;362-367.
18. Nagai T., Moriguchi R., Suzuki Y., Tomimori T., Yamada H. Mode of action of the anti-influenza virus activity of plant flavonoid, 5,7,4′-trihydroxy-8-methoxyflavone, from the roots of Scutellaria baicalensis. Antiviral Res. 26:1995;11-25.
19. Nakagawa Y., Kimura N., Toyoda T., Mizumoto K., Ishihama A., Oda K., Nakada S. The RNA polymerase PB2 subunit is not required for replication of the influenza virus genome but is involved in capped mRNA synthesis. J. Virol. 69:1995;728-733.
20. Nakagawa Y., Oda K., Nakada S. The PB1 subunit alone can catalyze cRNA synthesis, and the PA subunit in addition to the PB1 subunit is required for viral RNA synthesis in replication of the influenza virus genome. J. Virol. 70:1996;6390-6394.
21. Nishiyama Y., Yamamoto N., Yamada Y., Daikoku T., Ichikawa Y., Takahashi K. Anti-herpesvirus activity of carbocyclic oxetanocin G in vitro. J. Antibiot. 42:1989;1854-1859.
22. Oka T., Honda T., Morokuma K., Ginnaga A., Ohkuma K., Sakoh M. Enhancing effects of pertussis toxin B oligomer on the immunogenicity of influenza vaccine administered intranasally. Vaccine. 12:1994;1255-1258.
23. Sakuma T., Saijo M., Suzutani T., Yoshida I., Saito S., Kitagawa M., Hasegawa S., Azuma M. Antiviral activity of oxetanocins against varicella-zoster virus. Antimicrob. Agents Chemother. 35:1991;1512-1514.
24. Shaw M.W., Arden N.H., Maassab H.F. New aspects of influenza viruses. Clin. Microbiol. Rev. 5:1992;74-92.
25. Shealy Y.F., Clayton J.D. Carbocyclic analogs of guanosine and 8-azaguanosine. J. Pharm. Sci. 62:1973;1432-1434.
26. Shigeta S., Mori S., Baba M., Ito M., Honzumi K., Nakamura K., Oshitani H., Numazaki Y., Matsuda A., Obara T., Shuto S., DeClercq E. Antiviral activities of ribavirin, 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide, and 6′-(R)-6′-C-methylneplanocin A against several ortho- and paramyxoviruses. Antimicrob. Agents Chemother. 36:1992;435-439.
27. Suzutani T., Machida H., Sakuma T., Azuma M. Effects of various nucleosides on antiviral activity and metabolism of 1-β-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil against herpes simplex virus types 1 and 2. Antimicrob. Agents Chemother. 32:1988;1547-1551.
28. Tamura S., Ishihara K., Miyata K., Aizawa C., Kurata T. Mechanism of enhancement of the immune responses to influenza vaccine with cholera toxin B subunit and a trace amount of holotoxin. Vaccine. 13:1995;339-341.
29. Thomas G.P., Forsyth M., Penn C.R., McCauley J.W. Inhibition of the growth of influenza viruses in vitro by 4-guanidino-2,4-dideoxy-N-acetylneuraminic acid. Antiviral Res. 24:1994;351-356.
30. 7GpppXm)-dependent endonuclease of influenza virus by 4-substituted 2,4-dioxobutanoic acid compounds. Antimicrob. Agents Chemother. 38:1994;2827-2837.
31. Toyoda T., Kobayashi M., Ishihama A. Molecular dissection of the influenza virus RNA polymerase: PB1 alone is able to catalyze RNA. Virus Genes. 12:1996;155-163.
32. Tuzikov A.B., Byramova N.E., Bovin N.V., Gambaryan A.S., Matrosovich M.N. Monovalent and polymeric 5N-thioacetamido sialosides as tightly-bound receptor analogs of influenza viruses. Antiviral Res. 33:1997;129-134.
33. Van Voris L.P., Newell P.M. Antivirals for the chemoprophylaxis and treatment of influenza. Semin. Respir. Infect. 7:1992;61-70.
34. Von Itzstein M., Wu W.-Y., Kok G.B., Pegg M.S., Dyason J.C., Jin B., Van Phan T., Smythe M.L., White H.F., Oliver S.W., Colman P.M., Varghese J.N., Ryan D.M., Woods J.M., Bethell R.C., Hotham V.J., Cameron J.M., Penn C.R. Rational design of potent sialidase-based inhibitors of influenza virus replication. Nature. 363:1993;418-423.