Synthesis and Structure-Activity relationships of cephalosporins, 2-isocephems, and 2-oxaisocephems with C-3' or C-7 catechol or related aromatics

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 12, 1996, Pages 2135-2149

  Tsuji, Koichi ^a   Tsubouchi, Hidetsugu ^a   Yasumura, Koichi ^a   Matsumoto, Makoto ^a   Ishikawa, Hiroshi ^a  

^a OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

1,3 Dihydroxy 4 pyridone; 2 Isocephem; Catechol; Cephalosporin; Pseudomonas aeruginosa

Indexed keywords

CEPHALOSPORIN DERIVATIVE;

ACINETOBACTER; ANTIMICROBIAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; PSEUDOMONAS AERUGINOSA; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTI-BACTERIAL AGENTS; AZTREONAM; CATECHOLS; CEFTAZIDIME; CEPHALOSPORINS; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MALE; MICE; MICE, INBRED ICR; MICROBIAL SENSITIVITY TESTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030468245     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(96)00217-9     Document Type: Article

References (41)

1. 1. Weinstein, M. J.; Juedemann, G. M.; Oden, E. M.; Wagman, G. H. Antimicrob. Agents Chemother. 1963, 1.
2. 2. Nomura, H.; Fugono, T.; Hitaka, T.; Minami, I.; Azuma, T.; Morimoto, S.; Masuda, T. J. Med. Chem. 1974, 17, 1312.
3. 3. O'Callaghan, C. H.; Acred, P.; Harper, P. B.; Ryan, D. M.; Kirby, S. M.; Harding, S. M. Antimicrob. Agents Chemother. 1980, 77, 876.
4. 4. Kato, M.; Inoue, M.; Mitsuhashi, S. Antimicrob. Agents Chemother. 1982, 22, 721.
5. 5. Sykes, R. B.; Bonner, D. P.; Bush, K.; Georgopapadakou, N. H. Antimicrob. Agents Chemother. 1982, 21, 85.
6. 6. Kropp, H.; Sundelof, J. G.; Kahan, J. S.; Kahan, F. M.; Birnbaum, J. Antimicrob. Agents Chemother. 1980, 17, 993.
7. 7. Zama, Y.; Ishiyama, N.; Saita, T.; Naito, T.; Hirose, M.; Yokoyama, M.; Asano, T.; Senda, H.; Sekine, K., Sanai, S. EP 251, 299, 1988.
8. 8. Mitsuhashi, S.; Maejima, T. 29th International Conference on Antimicrobial Agents and Chemotherapy, Huston, 1989; Abstr. No. 482.
9. 9. Sakagami, K.; Iwamatsu, K.; Atsumi, K.; Hatanaka, M. Chem. Pharm. Bull. 1990, 38, 3476.
10. 10. Ogino, H.; Iwamatsu, K..; Katano, K.; Nakabayashi, S.; Yoshida, T.; Tsuruoka, T.; Inouye, S; Kondo, S. J. Antibiot. 1990, 43, 174.
11. 11. Ogino, H.; Iwamatsu, K.; Katano, K.; Nakabayashi, S.; Yoshida, T.; Shibahara, S.; Tsuruoka, T.; Inouye, S. J. Antibiot. 1990, 43, 189.
12. 12. Sakagami, K.; Iwamatsu, K.; Atsumi, K.; Hatanaka, M. Chem. Pharm. Bull. 1990, 38, 2271.
13. 13. Iwamatsu, K.; Atsumi, K.; Sakagami, K.; Ogino, H.; Yoshida, T.; Tsuruoka, T.; Shibahara, S.; Inouye, S.; Kondo, S. J. Antibiot. 1990, 43, 1450.
14. 14. Arnould, J. C.; Bertrandie, A.; Bird, T. G. C.; Boucherot, D.; Jung, F.; Lohmann, J. J.; Olivier, A.; Bailey, J. P.; Bell, W.; Davies, G. M. J. Med. Chem. 1992, 35, 2631.
15. 15. Sakagami, K.; Iwamatsu, K.; Atsumi, K.; Hatanaka, M. J. Antibiot. 1992, 45, 595.
16. 16. Okita, T.; Imae, K.; Hasegawa, T.; Iimura, S.; Masuyoshi, S.; Kamachi, H.; Kamei, H. J. Antibiot. 1993, 46, 833.
17. 17. Imae, K.; Iimura, S.; Hasegawa, T.; Okita, T.; Hirano, M.; Kamachi, H.; Kamei, H. J. Antibiot. 1993, 46, 840.
18. 18. Iimura, S.; Imae, K.; Hasagawa, T.; Okita, T.; Tamaoka, M.; Murata, S.; Kamachi, H.; Kamei, H. J. Antibiot. 1993, 46, 850.
19. 19. Aszodi, J.; Bonnet, A.; Chantot, J.-F.; Costerousse, G.; Teutsch, G. in Recent Advances in the Chemistry of β-Lactam Antibiotics; Bentley, P. H.; Southgate, R., Eds., Royal Society of Chemistry, Special Publication No. 70: London, 1988; p. 350.
20. 20. Bryan, D. B.; Hall, R. F.; Holden, K. G.; Huffman, W. F.; Gleason, J. G. J. Am. Chem. Soc. 1977, 99, 2353.
21. 21. Aszodi, J.; Chantot, J.-F.; Collard, J.; Teutsch, G. Heterocycles 1989, 28, 1061.
22. 22. Hakimelahi, G. H.; Shiao, M.-J.; Hwu, J. R. Helv. Chim. Acta 1992, 75, 1840.
23. 23. Aszodi, J.; Bonnet, A.; Chantot, J.-F.; Costerousse, G.; Didierlaurent, S.; Teutsch, G. BioMed. Chem. Lett. 1993, 3, 2231.
24. 24. Tsuji, K.; Ishikawa, H. BioMed. Chem. Lett. 1994, 4, 1601.
25. 25. Tsuji, K.; Yasumura, K.; Ishikawa, H. BioMed. Chem. Lett. 1995, 5, 963.
26. 26. Tsubouchi, H.; Tsuji, K.; Yasumura, K.; Tada, N.; Nishitani, S.; Minamikawa, J.; Ishikawa, H. Tetrahedron: Asymmetry 1994, 5, 441.
27. 27. Goerdeler, J.; Ohm, J.; Tegtmeyer, O. Chem. Ber. 1956, 89, 1534.
28. 28. Li, J.; Wang, X.; Huang, J. Zhongguo Yiyao Gongye Zazhi, 1995, 26, 518.
29. 29. Demaree, P.; Doria, M. C.; Muchowski, J. M. J. Heterocycl. Chem. 1978, 15, 1295.
30. 30. Tsuji, T.; Satoh, H.; Narisada, M.; Hamashima, Y.; Yoshida, T. J. Antibiot. 1985, 38, 466.
31. 31. Gottstein, W. J.; Kaplan, M. A.; Cooper, J. A.; Silver, V. H.; Nachfolger, S. J.; Granatek, A. P. J. Antibiot. 1976, 29, 1226.
32. 32. Haro, Y.; Fujise, S. Pharm. Bull. 1954, 2, 156.
33. 33. Tsuchihashi, G.; Ogura, K. JP 47-42760, 1972.
34. 34. Smith, P. W.; Chamiec, A. J.; Chung, G.; Cobley, K. N.; Duncan, K.; Howes, P. D.; Whittington, A. R.; Wood, M. R. J. Antibiot. 1995, 48, 73.
35. 35. Tsuji, T.; Itani, H.; Ishitobi, H. Tetrahedron Lett. 1987, 28, 2745.
36. 36. Nishimura, T.; Yoshimura, Y. Yamaoka, M.; Kawai, T.; Miyake, A. J. Antibiot. 1991, 44, 1371.
37. 37. Kossmehl, G.; Frohberg, H. C. Chem Ber. 1986, 119, 50.
38. 38. This compound was prepared in a similar manner to the procedure described for the preparation of 2-chloromethyl-5-benzyloxy-4-pyridone; Yamanaka, H.; Yoshida, Y.; Goto, J.; Terasawa, T.; Okuda, S.; Sakane, K. EP 345,671, 1989.
39. 39. Tsubouchi, H.; Tsuji, K.; Yasumura, K.; Matsumoto, M.; Shitsuta, T.; Ishikawa, H. J. Med. Chem. 1995, 38, 2152.
40. 40. Japan Society of Chemotherapy, Chemotherapy 1981, 29, 76.
41. 41. Shishido, H.; Nagai, H.; Nishino, T. Kagakuryouhouno Ryouiki 1991, 7, 125.