Synthesis of 3-Acylamino-4-hydroxymethy1-2-oxo-1-sulfoazetidines and Related Compounds

Chemical and Pharmaceutical Bulletin

Volumn 32, Issue 4, 1984, Pages 1303-1312

  Shibuya, Masayuki ^a   Jinbo, Yoshikazu ^a   Kubota, Seiju ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

3,3,6,9,9 pentamethyl 2,10 diazabicyclo 4.4.0 1 decene (2,2,4a,7,7 pentamethyl l,2,3,4,4a,5,6,7 octahydronaphthyridine); 4 acetoxymethyl 2 azetidinone; 4 hydroxymethyl 2 azetidinone; L malic acid; N sulfoazetidinone; sulfonation

Indexed keywords

ANTI INFECTIVE AGENTS; ANTIINFECTIVE AGENT; AZETIDINE DERIVATIVE; AZTREONAM; BETA LACTAM ANTIBIOTIC; NEW DRUG;

ARTICLE; CHEMISTRY; MICROBIOLOGICAL EXAMINATION; SYNTHESIS; 3 AMINO 4 HYDROXYMETHYL 2 OXO 1 AZETIDINESULFONIC ACID DERIVATIVE; 4 ACETOXYMETHYL 2 AZETIDINONE DERIVATIVE; 4 ACETOXYMETHYL 3 [2 (2 AMINO 4 THIAZOLYL) 2 METHOXYIMINOACETAMIDO] 2 OXO 1 AZETIDINESULFONIC ACID; 4 HYDROXYMETHYL 2 AZETIDINONE DERIVATIVE; DRUG ANALYSIS; DRUG COMPARISON; DRUG IDENTIFICATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

ANTI-INFECTIVE AGENTS; ANTIBIOTICS, LACTAM; AZETIDINES; AZETINES; AZTREONAM; CHEMISTRY; MICROBIAL SENSITIVITY TESTS;

EID: 0021266177     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.32.1303     Document Type: Article

References (29)

1. A. Imada, K. Kitano, K. Kintaka, M. Muroi, and M. Asai, Nature (London), 289, 590 (1981).
2. R. B. Sykes, C. M. Cimarusti, D. P. Bonner, K. Bush, D. M. Floyd, N. H. Georgopapadakou, W. H. Koster, W. C. Liu, W. L. Parker, P. A. Principe, M. L. Rathnum, W. A. Slusarchyk, W. H. Trejo, and J. S. Wells, Nature, 291, 489 (1981).
3. M. Asai, K. Haibara, M. Muroi, K. Kintaka, and T. Kishi, J.Antibiot., 34, 621(1981); K. Kintaka, K. Haibara, M. Asai, and A. Imada, J. Antibiot., 34, 1081 (1981).
4. K. Kintaka, K. Haibara, M. Asai, and A. Imada, J. Antibiot., 34, 1081 (1981).
5. J. S. Wells, W. H. Trejo, P. A. Principe, K. Bush, N. Georgopapadakou, D. P. Bonner, and R. B. Sykes, J. Antibiot., 35, 184 (1982).
6. W. L. Parker and M. L. Rathnum, J. Antibiot., 35, 300 (1982).
7. D. M. Floyd, A. W. Fritz, and C. M. Cimarusti, J. Org. Chem., 47, 176 1982.
8. C. M. Cimarusti, H. E. Applegate, H. W. Chang, D. M. Floyd, W. H. Koster, W. A. Slusarchyk, and M. G. Young, J. Org. Chem., 47, 179 (1982).
9. D. M. Floyd, A. W. Fritz, J. Pluscec, E. R. Weaver, and C. M. Cimarusti, J. Org. Chem., 47, 5160 (1982).
10. A. J. Biloski, R. D. Wood, and B. Ganem, J. Am. Chem. Soc., 104, 3233 (1982).
11. W. C. Liu, W. L. Parker, J. S. Wells, P. A. Principe, W. H. Trejo, D. P. Bonner, and R. B. Sykes, 12th International Congress of Chemotherapy, No. 939, Florence, Italy, July 1981.
12. C. M. Cimarusti, R. B. Sykes, H. W. Applegate, D. P. Bonner, H. Breuer, H. W. Chang, T. Denzel, D. M. Floyd, A. Fritz, W. H. Koster, W. C. Liu, W. L. Parker, M. L. Rathnum, W. A. Slusarchyk, U. Treuner, and M. Young, 182nd National Meeting of the American Chemical Society, New York, August 1981.
13. T. Takaya, H. Takasugi, T. Masugi, T. Chiba, H. Kochi, T. Takano, and H. Nakano, Nippon Kagaku Kaishi, 1981, 785.
14. P. Baumgarten, Berichte, 59, 1166 (1926).
15. G. W. Kenner and R. J. Stedman, J. Chem. Soc., 1952, 2069.
16. D. W. Clayton, J. A. Farrington, G. W. Kenner, and J. M. Turner, J. Chem. Soc., 1957, 1398.
17. C. S. Rondesvedt, Jr. and F. G. Bordwell, Org. Syn., Coll. Vol., 4, 846 (1963).
18. P. Bourgeois and N. Duffaut, Bull. Soc. Chim. Fr., 1980, 11-195.
19. I. J. Galpin, G. W. Kenner, and A. Marston, Bioorg. Chem., 8, 323 (1979).
20. M. Shibuya, Y. Jinbo, and S. Kubota, Heterocycles, 20, 1531 (1983).
21. F. Heinzer, M. Soukup, and A. Eschenmoser, Helv. Chim. Acta, 61, 2851 (1978). This amidine base is abbreviated as PDBD throughout this paper.
22. T. N. Salzmann, R. W. Ratcliffe, B. G. Christensen, and F. A. Bouffard, J. Am. Chem. Soc., 102, 6163 (1980).
23. M. J. Miller, J. S. Bajwa, P. G. Mattingly, and K. Peterson, J. Org. Chem., 47, 4928 (1982).
24. P. G. Mattingly and M. J. Miller, J. Org. Chem., 45, 410 (1980).
25. M. J. Miller, P. G. Mattingly, M. A. Morrison, and J. F. Kerwin, Jr., J. Am. Chem. Soc., 102, 7026 (1980).
26. O. Mitsunobu, Synthesis, 1981, 1.
27. K. Kiihlein and H. Jensen, Justus Liebigs Ann. Chem., 1974, 369.
28. R. E. Harmon, G. Wellman, and S. K. Gupta, J. Org. Chem., 38, 11 (1973).
29. M. Shibuya and S. Kubota, Heterocycles, 14, 601 (1980).