A potent and selective inhibition of parainfluenza 1 (Sendai) virus by new 6-oxiranyl-, 6-methyloxiranyluracils, and 4(3H)-pyrimidinone derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 14, 1998, Pages 1833-1838

  Saladino, Raffaele ^a   Danti, Maria Chiara ^a   Mincione, Enrico ^a   Crestini, Claudia ^a   Palamara, Anna Teresa ^b   Savini, Patrizia ^b   Marini, Stefano ^b   Botta, Maurizio ^c  

^a UNIVERSITY OF TUSCIA   (Italy)

^b UNIVERSITY OF ROME TOR VERGATA   (Italy)

^c UNIVERSITY OF SIENA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; PYRIMIDINONE DERIVATIVE;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; NONHUMAN; PARAINFLUENZA VIRUS 1; SENDAI VIRUS; VIRUS INFECTION; VIRUS REPLICATION;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE; DOGS; PYRIMIDINONES; RESPIROVIRUS; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

ANIMALIA; HUMAN PARAINFLUENZA VIRUS 1; PARAINFLUENZA 1 VIRUS; SENDAI VIRUS;

EID: 0032555174     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00314-X     Document Type: Article

References (33)

1. 1. Collins, P. L.; Chanock, R. M.; McIntosh, K. Parainfluenza Viruses in: Fields Virology; Fields, B. N., Knipe DM, and Howley, P. M. et al. Eds, Lippincott-Raven Publishers Philadelphia. 1996; pp.1205-1241.
2. 2. Chanock, R. M.; Parrot, R. H.; Cook, K. N. Engl. J. Med. 1958, 258, 207-213.
3. 3. (a) Ishida, N.; Homma, M. Advansed in Virus Research. 1978, 23, 349-383.
4. (b) Amici, C.; Palamara, A. T.; Garaci, E.; Santoro, M. G. Antiv. Res. 1992, 19, 129-138.
5. 4. Rapaport, D.; Ovadia, M.; Shai, Y. EMBO Journal 1995, 14, 5524-5531.
6. 5. Hayashi, T.; Hotta, H.; Itoh, M.; Homma, M. Journal of General Virology 1991, 72, 979-982.
7. 6. Borkow, G.; Ovadia, M. Antiviral Res. 1994, 23, 161-176.
8. 7. Horvath, C. M.; Lamb, R. A. J. Virol. 1992, 66, 2443-2455.
9. 8. Ono, A.; Kawakita, M. J. Biochem. 1994, 116, 649-656.
10. 9. Iliescu, R.; Calinoiu, A.; Repanovici, R.; Popa, L. M.; Lober, G. Studia Biophysica 1987, 117, 111-116.
11. 10. Iida, J.; Ishihara, C.; Mizukoshi, N.; Kitoh, K.; Tsukidate, K.; Katsu, K.; Toyosawa, T.; Azuma, I. Vaccine 1990, 8, 376-380.
12. 11. Kimsey, P. B.; Pecquet, G. M. E.; Zhi-Bo, Z.; Brackee, G.; Fox, J. G. Am. Rev. Respir. Dis. 1989, 140, 1704-1711.
13. 12. (a) Das, P.; Spears, C. P.; Shahinian, A. H.; Dasgupta, S. K.; Kundu, N. G. Biorganic & Medicinal Chem. Lett. 1996, 20, 2477-2480.
14. (b) Felczak, K.; Drabikowska, A. K.; Vilpo, J. A.; Kulikowski, T.; Shugar, D. J. Med. Chem. 1996, 39, 1720-1728.
15. (c) Botta, M.; Saladino, R.; Occhionero, F.; Nicoletti, R. Trends in Organic Chemistry 1995, 5, 57.
16. 13. (a) Kim, D.-K.; Gam, J.; Kim, Y.-W.; Lim, J.; Kim, H.-T.; Kim K.H. J. Med. Chem. 1997, 40, 2363-2373.
17. (b) Pontikis, R.; Benhida, R.; Aubertin, A.-M.; Grierson, D. S.; Monneret, C. J. Med. Chem. 1997, 40, 1845-1854.
18. (c) Mai, A.; Artico, M.; Sbardella, G.; Quartarone, S.; Massa, S.; Loi, A. G.; De Montis, A.; Scintu, F.; Putzolu, M.; La Colla, P. J. Med. Chem. 1997, 40, 1447-1454.
19. (d) Danel, K.; Larsen, E.; Pedersen, E.B.; Vestergaard, B.F.; Nielsen, C. J. Med. Chem. 1996, 39, 2427-2431.
20. (e) Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Inouye, N.; Baba, M.; Shigeta, S.; Walker, R. T.; De Clercq, E.; Miyasaka, T. J. Med. Chem. 1995, 38, 2860 and references cited therein.
21. (f) Mai, A.; Artico, M.; Sbardella, G.; Massa, S.; Loi, A. G.; Tramontano, E.; Scano, P.; La Colla, P. J. Med. Chem. 1995, 38, 3258 and references cited therein.
22. 14. (a) Botta, M.; Saladino, R.; Gambacorta, A.; Nicoletti, R. Tetrahedron Asymmetry 1990, 1, 441-444.
23. (b) Botta, M.; Saladino, R.; Lamba, D.; Nicoletti, R. Tetrahedron 1993, 49, 6053-6070.
24. 15. (a) Saladino, R.; Crestini, C.; Bernini, R.; Mincione, E.; Ciafrino, R. Tetrahedron Lett. 1995, 15, 2665-2668.
25. (b) Saladino, R.; Stasi, L.; Crestini, C.; Nicoletti, R.; Botta, M. Tetrahedron 1997, 53, 7045-7056.
26. 16. Saladino, R.; Bernini, R.; Crestini, C.; Mincione, E.; Bergamini, A.; Marini, S.; Palamara, A. T. Tetrahedron 1995, 51, 7561-7578.
27. 17. Garaci, E.; Palamara, A. T.; Di Francesco, P.; Favalli, C.; Ciriolo, M. R.; Rotilio, G. Biochem. and Bioph. Res. Comm. 1992, 188, 1090-1096.
28. 18. Botta, M.; Saladino, R.; Nicoletti, R. Heterocycles 1991, 32, 1537.
29. 19. Botta, M.; Saladino, R.; Delle Monache, G.; Gentile, G.; Nicoletti, R. Heterocycles 1996, 8, 1687-1697.
30. 2 in MeOH at 25°C.
31. 2 in MeOH at 25°C.
32. 22. Compounds 7 and 8 were prepared by trans-alkoxylation reactions starting from 2-methoxy-6-methyl-4(3H)-pyrimidinone and appropriate sodium alkoxylates as reported in: Botta, M.; De Angelis, F.; Finizia, G.; Gambacorta, A.; Nicoletti, R. Synthetic Comm. 1985, 15, 27.
33. 13C-NMR spectroscopy. All new compounds gave satisfactory (0.4% of the theoretical values) elemental analyses.