Synthesis of new quinolone antibiotics utilizing azetidine derivatives obtained from 1-azabicyclo[1.1.0]butane

Chemical and Pharmaceutical Bulletin

Volumn 56, Issue 3, 2008, Pages 346-356

  Ikee, Yoshifumi ^a   Hashimoto, Kana ^a   Kamino, Mai ^a   Nakashima, Masaaki ^a   Hayashi, Kazuhiko ^b   Sano, Shigeki ^a   Shiro, Motoo ^c   Nagao, Yoshimitsu ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b KINJO GAKUIN UNIVERSITY   (Japan)

^c RIGAKU CORPORATION   (Japan)

Author keywords

Antibacterial agent; Azabicyclobutane; Azetidine; Methicillin resistant Staphylococcus aureus; New quinolone

Indexed keywords

1 AZABICYCLO[1.1.0]BUTANE; 1 CYCLOPROPYL 6,8 DIFLUORO 7 (1 METHYLTETRAZOL 5 YL) 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 7 (3 DIBENZYLAMINOAZETIDIN 1 YL) 6,8 DIFLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 6,8 DIFLUORO 7 [3 (METHOXYANILINO)AZETIDIN 1 YL] 4 OXO 1 (1 METHYL 2 OXO 1,2 DIHYDROPYRIMIDIN 2 YL) 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 6,8 DIFLUORO 7 [3 (METHOXYANILINO)AZETIDIN 1 YL] 4 OXO 1 (PYRIMIDIN 2 YL) 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 6,8 DIFLUORO 7 [3 (METHOXYANILINO)AZETIDIN 1 YL] 4 OXO 1 (THIAZOL 2 YL) 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; AROMATIC AMINE; AZETIDINE DERIVATIVE; BENZYL BROMIDE; DIBENZYLAMINE; HETEROCYCLIC COMPOUND; LEVOFLOXACIN; MAGNESIUM DERIVATIVE; N BENZYL 3 BROMOAZETIDINE; QUINOLINE DERIVED ANTIINFECTIVE AGENT; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; RING OPENING; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; AZABICYCLO COMPOUNDS; AZETIDINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRYSTALLOGRAPHY, X-RAY; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; METHICILLIN RESISTANCE; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; QUINOLONES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STAPHYLOCOCCUS AUREUS;

EID: 41549087781     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.56.346     Document Type: Article

References (42)

1. Hayashi K., Sato C., Hiki S., Kumagai T., Tamai S., Abe T., Nagao Y., Tetrahedron Lett., 40, 3761-3764 (1999).
2. Funke W., Angew. Chem., Int. Ed. Engl., 80, 70-71 (1969).
3. Funke W., Chem. Ber., 102, 3148-3158 (1969).
4. Hortmann A. G., Robertson D. A., J. Am. Chem. Soc., 94, 2758-2765 (1972).
5. Marchand A. P., Rajagopal D., Bott S. G., J. Org. Chem., 60, 4943-4946 (1995).
6. Dave P. R., J. Org. Chem., 61, 5453-5455 (1996).
7. Bartnik R., Marchand A. P., Synlett, 1997, 1029-1039 (1997).
8. Hayashi K., Ikee Y., Goto S., Shiro M., Nagao Y., Chem. Pharm. Bull., 52, 89-94 (2004).
9. Hayashi K., Hiki S., Kumagai T., Nagao Y., Heterocycles, 56, 433-442 (2002).
10. Ikee Y., Hashimoto K., Nakashima M., Hayashi K., Sano S., Shiro M., Nagao Y., Bioorg. Med. Chem. Lett., 17, 942-945 (2007).
11. Pinder A. R., Nat. Prod. Rep., 9, 491-504 (1992)
12. Frigola J., Parés J., Corbera J., Vañó D., Mercè R., Torrens A., Más J., Valentí E., J. Med. Chem., 36, 801-810 (1993).
13. Frigola J., Torrens A., Castrillo J. A., Mas J., Vañó D., Berrocal J. M., Calvet C., Salgado L., Redondo J., García-Granda S., Valentí E., Quintana J. R., J. Med. Chem., 37, 4195-4210 (1994).
14. Frigola J., Vañó D., Torrens A., Gómez-Gomar A., Ortega E., García-Granda S., J. Med. Chem., 38, 1203-1215 (1995).
15. Kuramoto Y., Ohshita Y., Yoshida J., Yazaki A., Shiro M., Koike T., J. Med. Chem., 46, 1905-1917 (2003).
16. Archibald T. G., Gilardi R., Baum K., George C., J. Org. Chem., 55, 2920-2924 (1990).
17. Hayashi K., Kumagai T., Nagao Y., Heterocycles, 53, 447-452 (2000).
18. Domagala J. M., J. Antimicrob. Chemother., 33, 685-706 (1994).
19. Drlica K., Curr. Opin. Microbiol., 2, 504-508 (1999).
20. Hooper D. C., Clin. Infect. Dis., 32, S9-S15 (2001).
21. Peterson L. R., Clin. Infect. Dis., 33, S180-S186 (2001).
22. Mitscher L. A., Chem. Rev., 105, 559-592 (2005).
23. Hooper D. C., Lancet. Infect. Dis., 2, 530-538 (2002).
24. Li X.-Z., Int. J. Antimicrob. Agents, 25, 453-463 (2005).
25. Lide D. R., "CRC Handbook of Chemistry and Physics," 81st ed., CRC Press, Boca Raton, Florida, 2000, pp. 8/44-8/56.
26. Grohe K., Heitzer H., Liebigs. Ann. Chem., 1987, 29-37 (1987).
27. Domagala J. M., Heifetz C. L., Hutt M. P., Mich T. F., Nichols J. B., Solomon M., Worth D. F., J. Med. Chem., 31, 991-1001 (1988).
28. Sanchez J. P., Bridges A. J., Bucsh R., Domagala J. M., Hagen S. E., Heifetz C. L., Joannides E. T., Sesnie J. C., Shapiro M. A., Szotek D. L., J. Med. Chem., 35, 361-367 (1992).
29. Ronald J. C., Thomas A. C., Gregory L. K., James W., Synthesis, 1993, 290-292 (1993).
30. Wentland M. P., Lesher G. Y., Reuman M., Gruett M. D., Singh B., Aldous S. C., Dorff P. H., Rake J. B., Coughlin S. A., J. Med. Chem., 36, 2801-2809 (1993).
31. 3, Z=4, R=0.063, Rw=0.061. CCDC-623357 (7b) contains the supplementary crystallographic date for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Date Centre via www.ccdc.cam.ac.uk/ date_request/cif.
32. Kuramoto Y., Medchem News, Vol. 17, No. 2, 2-7 (2007).
33. Hayashi N., Nakata Y., Yazaki A., Antimicrob. Agents Chemother., 48, 799-803 (2004).
34. Barnick J. W. F. K., Van Der Baan J. L., Bickelhaupt F., Synthesis, 1979, 787-788 (1979).
35. 3, Z=4, R=0.0822, Rw=0.1333. CCDC-671163 (27a) contains the supplementary crystallographic date for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Date Centre via www.ccdc.cam.ac.uk/ date_request/cif.
36. Japan Society of Chemotherapy, Chemotherapy, 29, 76-79 (1981).
37. Hayakawa I., Atarashi S., Yokohama S., Imamura M., Sakano K., Frukawa M., Antimicrob. Agents Chemother., 29, 163-164 (1986).
38. Atarashi S., Yokohama S., Yamazaki K., Sakano K., Imamura M., Hayakawa I., Chem. Pharm. Bull., 35, 1896-1902 (1987).
39. Suzuki Y., Tsukamoto K., Hasegawa Y., Hiramatsu Y., Japan Kokai Tokkyo Koho, JP S49-109369 (1974).
40. Chen Z., Kolb H. C., Richardson P., Hung Z., PCT Int. Appl. WO 2000063168 (2000).
41. Luzzio M. J., Marx M. A., Yong B. V., PCT Int. Appl. WO 2001094353 (2001).
42. Tomita K., Tsuzuki Y., Shibamori K., Tashima M., Kajikawa F., Sato Y., Kashimoto S., Chiba K., Hino K., J. Med. Chem., 45, 5564-5575 (2002).