Synthesis and Structure-Activity Relationships of Antibacterial Phosphonopeptides Incorporating (1-Aminoethyl)phosphonic Acid and (Aminomethyl)phosphonic Acid

Journal of Medicinal Chemistry

Volumn 29, Issue 1, 1986, Pages 29-40

  Atherton, Frank R ^a   Hassall, Cedric H ^a   Lambert, Robert W ^a  

^a ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALAFOSFALIN; ANTIINFECTIVE AGENT; NEW DRUG;

1 AMINOETHYLPHOSPHONIC ACID; ALANYLALANYL(1 AMINOETHYL)PHOSPHONIC ACID; AMINOMETHYLPHOSPHONIC ACID; ANIMAL EXPERIMENT; DRUG ANALYSIS; DRUG COMPARISON; DRUG EFFICACY; DRUG IDENTIFICATION; DRUG METABOLISM; DRUG SCREENING; DRUG STABILITY; DRUG SYNTHESIS; IN VITRO STUDY; MOUSE; NONHUMAN; OMEGA PHOSPHONOAMINOACID; ORAL DRUG ADMINISTRATION; PHOSPHONODIPEPTIDE; PHOSPHONOOLIGOPEPTIDE; PRIORITY JOURNAL; SARCOSYLNORVALYLNORVALYL(1 AMINOETHYL)PHOSPHONIC ACID; STRUCTURE ACTIVITY RELATION; SUBCUTANEOUS DRUG ADMINISTRATION;

ALANINE; AMINOETHYLPHOSPHONIC ACID; ANIMAL; ANTIBIOTICS; BACTERIA; BIOLOGICAL TRANSPORT, ACTIVE; CHEMISTRY; COMPARATIVE STUDY; ESCHERICHIA COLI; ESCHERICHIA COLI INFECTIONS; HAEMOPHILUS INFLUENZAE; MICE; ORGANOPHOSPHORUS COMPOUNDS; PEPTIDES; STREPTOCOCCUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0022577081     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00151a005     Document Type: Article

References (32)

1. Allen, J.G.; Atherton, F.R.; Hall, M.J.; Hassall, C.H.; Holmes, S.W.; Lambert, R.W.; Nisbet, L.J.; Ringrose, P.S. Nature (London) 1978, 272, 56.
2. Atherton, F.R.; Hall, M.J.; Hassall, C.H.; Lambert, R.W.; Ringrose, P.S. Antimicrob. Agents Chemother. 1979, 15, 677.
3. Allen, J.G.; Atherton, F.R.; Hall, M.J.; Hassall, C.H.; Holmes, S.W.; Lambert, R.W.; Nisbet, L.J.; Ringrose, P.S. Antimicrob. Agents Chemother. 1979, 15, 684.
4. Atherton, F.R.; Hall, M.J.; Hassall, C.H.; Lambert, R.W.; Lloyd, W.J.; Ringrose, P.S. Antimicrob. Agents Chemother. 1979, 15, 696.
5. Atherton, F.R.; Hall, M.J.; Hassall, C.H.; Holmes, S.W.; Lambert, R.W.; Lloyd, W.J.; Ringrose, P.S. Antimicrob. Agents Chemother. 1980, 18, 897.
6. Atherton, F.R.; Hall, M.J.; Hassall, C.H.; Holmes, S.W.; Lambert, R.W.; Lloyd, W.J.; Nisbet, L.J.; Ringrose, P.S.; Westmacott, D. Antimicrob. Agents Chemother. 1981, 20, 470.
7. Atherton, F.R.; Hall, M.J.; Hassall, C.H.; Lambert, R.W.; Lloyd, W.J.; Ringrose, P.S.; Westmacott, D. Antimicrob. Agents Chemother. 1982, 22, 571.
8. Gilmore, W.F.; McBride, H.A. J. Pharm. Sci. 1974, 63, 1087.
9. Huber, J.R.; Gilmore, W.F.; Robertson, L.W. J. Med. Chem. 1975, 18, 106.
10. Okada, Y.; Iguchi, S.; Mimura, M.; Yagyu, M. Chem. Pharm. Bull. 1980, 28, 1320.
11. Kametani, T.; Suzuki, Y.; Kigasawa, K.; Hiiragi, M.; Wakisaka, K.; Sugi, H.; Tanigawa, K.; Fukawa, K.; Orino, S.; Al. Heterocycles 1982, 18, 295.
12. Kametani, T. Heterocycles 1981, 16, 1205.
13. Kupczyk-Subotkowska, L.; Kafarski, P.; Kowalik, J.; Lejczak, B.; Masterlerz, P.; Oleksyszyn, J.; Szewczyk, J. ACS Symp. Ser. 1981, 171, 187.
14. Szewczyk, J.; Lejczak, B.; Kafarski, P. Experientia 1982, 38, 983.
15. Kafarski, P.; Lejczak, B.; Mastalerz, P.; Szewczyk, J.; Wasielewski, C. Can. J. Chem. 1982, 60, 3081.
16. Chambers, J.R.; Isbell, A.F. J. Org. Chem. 1964, 29, 832.
17. Olsen, R.K. J. Org. Chem. 1970, 35, 1912.
18. Arfin, S.M.; Koziell, D.A. J. Bacteriol. 1971, 105, 519.
19. Greenstein, J.P.; Winitz, M. “Chemistry of the Amino Acids”; Wiley: New York, 1961; pp 22, 33, 1415.
20. Atherton, F.R.; Hall, M.J.; Hassall, C.H.; Lambert, R.W.; Lloyd, W.J.; Lord, A.V.; Ringrose, P.S.; Westmacott, D. Antimicrob. Agents Chemother. 1983, 24, 552.
21. Payne, J.W. In “Peptide Transport in Protein Nutrition”; Matthews, D.M., Payne, J.W., Ed.; North-Holland Elsevier: Amsterdam, 1975
22. Cheung, K.-S.; Wasserman, S.A.; Dudek, E.; Lerner, S.A.; Johnston, M. J. Med. Chem. 1983, 26, 1733.
23. Wang, E.; Walsh, C. Biochemistry 1978, 17, 1313.
24. Wang, E.; Walsh, C. Biochemistry 1981, 20, 7539.
25. Neuhaus, F.C.; Hammes, W.P. Pharmacol. Ther. 1981, 14, 265.
26. Allen, J.G.; Havas, L.; Leicht, E.; Lenox-Smith, I.; Nisbet, L. J. Antimicrob. Agents Chemother. 1979, 16, 306.
27. Allen, J.G.; Lees, L. J. Antimicrob. Agents Chemother. 1980, 17, 973.
28. Hassall, C.H. In “Antibiotics”; Hahn, F.E., Ed.; Springer-Verlag: Berlin, 1983.
29. Anderson, G.W.; Zimmerman, J.E.; Callahan, F.M. J. Am. Chem. Soc. 1964, 86, 1839.
30. Pless, J.; Boissonnas, R.A. Helv. Chim. Acta 1963, 46, 1609.
31. Greenstein, J.P.; Winitz, M. “Chemistry of the Amino Acids”; Wiley: New York, 1961; Vol. 2, p 891.
32. Tipson, R.S.; Pawson, B.A. J. Org. Chem. 1961, 26, 4698.