Synthesis and morphological reversion activity on src(ts)NRK cells of pyrimidinylpropanamide antibiotics, sparsomycin, sparoxomycin A1, A2, and their analogues

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 23, 1998, Pages 3331-3334

  Nakajima, Noriyuki ^a   Enomoto, Takeshi ^a   Matsuura, Nobuyasu ^a   Ubukata, Makoto ^a  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; PROPIONAMIDE DERIVATIVE; PYRIMIDINE DERIVATIVE; SPAROXOMYCIN A1; SPAROXOMYCIN A2; SPARSOMYCIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

EID: 0032401082     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00604-0     Document Type: Article

References (32)

1. 1. a) Argoudelis, A. D.; Herr, R. R.Antimicrob. 1962, 505.
2. b) Higashide, E.; Hasegawa, T.; Shibata, M.; Mizuno, K.; Akaike, H. Takeda Kenkyusho Nempo 1966, 25, 1; Chem. Abstr. 1967, 66, 54238.
3. b) Higashide, E.; Hasegawa, T.; Shibata, M.; Mizuno, K.; Akaike, H. Takeda Kenkyusho Nempo 1966, 25, 1; Chem. Abstr. 1967, 66, 54238.
4. 2. a) Helquist, P.; Shekhani, M. S. J. Am. Chem. Soc. 1979, 101, 1057.
5. b) Wang, D-R.H.; Helquist, P.; Shekhani, M. S. J. Org. Chem. 1985, 50, 1264.
6. 3. b) Ottenheijm, H. C. J.; Liskamp, R. M. J.; Tijhuis, M. W. Tetrahedron Lett. 1979, 387.
7. b) Ottenheijm, H. C. J.; Liskamp, R. M. J. Tetrahedron Lett. 1978, 2437.
8. c) Ottenheijm, H. C. J., Liskamp, R. M. J.; van Nispen, S. P. J.; Boots, H. A.; Tijhuis, M. W. J. Org. Chem. 1981, 46, 3273.
9. 4. a) Ubukata, M.; Morita, T.; Kakeya, H.; Kobinata, K.; Kudo, T.; Osada, H. J. Antibiotics 1996, 49, 65.
10. b) Ubukata, M.; Morita, T.; Uramoto, M.; Osada, H. J. Antibiotics 1996, 49, 1096.
11. 5. a) Lin, C-C L.; Dubois, R. J. J. Med. Chem., 1977, 20, 337.
12. b) Liskamp, R. M. J.; Colstee, J. H.; Ottenheijm, H. C. J.; Lelieveld, P.; Akkermann, W. J. Med. Chem., 1984, 27, 301.
13. 6. Uehara, Y.; Hori, M.; Takeuchi, T.; Umezawa, H., Jap. J. Cancer Res. (Gann), 1985, 76, 672.
14. 7. a) Pitchen, P.; Dunach, E.; Deshmukh, M. N.; Kagan, H. B. J. Am. Chem. Soc. 1984, 106, 8188.
15. b) Zhao, S. H.; Samuel, O.; Kagan, H. B. Tetrahedron 1987, 43, 5135.
16. c) Kagan, H. B; Rebiere, F. Synlett, 1990, 643.
17. d) Brunel, J -M.; Diter, P.; Duetsch, M.; Kagan, H. B. J. Org. Chem. 1995, 60, 8086.
18. 8. a) Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703.
19. b) Davis, F. A.; ThimmaReddy, R.; Weismiller, M. C. J. Am. Chem. Soc. 1989, 111, 5964.
20. 9. a) Komatsu, N.; Nishibayashi, Y.; Sugita, T.; Uemura, A. Tetrahedron Lett. 1992, 33, 5391.
21. b) Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, A. J. Org. Chem. 1993, 58, 4529.
22. 10. Palucki, M.; Hanson, P.; Jacobsen, E, N. Tetrahedron Lett. 1992, 33, 7111.
23. 11. a) Noda, K.; Hosoya, N.; Yanai, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1994, 35, 1887.
24. b) Noda, K.; Hosoya, N.; Irie, R.; Yamashita, Y.; Katsuki, T. Tetrahedron 1994, 50, 9609.
25. 2, toluene), and the reaction temperature were each studied.
26. tR(K)-11, 15.3 (7.5 %).
27. 5NS, 316.1218; found, 316.1202.
28. 15. Under the stereoselective oxidation conditions for 10 to 11, the reaction did not proceed.
29. 16. Johnson, C. R.; Keiser, J. E. "Organic Synthesis"; Wiley: New York, 1973; Coll. Vol. V, p791.
30. 16. Johnson, C. R.; Keiser, J. E. "Organic Synthesis"; Wiley: New York, 1973; Coll. Vol. V, p791.
31. 4a
32. tSNRK cells were observed under a microscope after 18 to 20 hours incubation at 32°C.