Synthesis and in vitro antibacterial activity of 7-(4-alkoxyimino-3-amino-3-methylpiperidin-1-yl)fluoroquinolone derivatives

European Journal of Medicinal Chemistry

Volumn 44, Issue 10, 2009, Pages 4063-4069

  Chai, Yun ^a   Wan, Zhi Long ^a   Wang, Bo ^a   Guo, Hui Yuan ^a   Liu, Ming Liang ^a  

^a INSTITUTE OF MEDICINAL BIOTECHNOLOGY   (China)

Author keywords

Antibacterial activity; Fluoroquinolone; Synthesis

Indexed keywords

1 CYCLOPROPYL 6,8 DIFLUORO 7 (3 AMINO 4 ETHOXYIMINO 3 METHYLPIPERIDIN 1 YL) 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID; LEVOFLOXACIN; QUINOLINE DERIVED ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG DESIGN; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; KLEBSIELLA PNEUMONIAE; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STREPTOCOCCUS PNEUMONIAE;

ANIMALS; ANTI-BACTERIAL AGENTS; BACTERIA; CELL SURVIVAL; CERCOPITHECUS AETHIOPS; FLUOROQUINOLONES; MICROBIAL SENSITIVITY TESTS; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS;

EID: 67651174298     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.04.041     Document Type: Article

References (20)

1. Domagala J.M., Heifetz C.L., Mich T.F., and Nichos J.B. J. Med. Chem. 29 (1986) 445-448
2. Hoshino K., Kitamura A., Morrissey I., Sato K., Kato J., and Ikeda H. Antimicrob. Agents Chemother. 38 (1994) 2623-2627
3. Hong C.Y., Kim Y.K., Lee Y.H., and Kwak J.H. Bioorg. Med. Chem. Lett. 8 (1998) 221-226
4. Piddock L.J.V. Antimicrob. Agents Chemother. 38 (1994) 163-169
5. Cecchetti V., Fravolini A., Lorenzini M.C., Tabarrini O., Terni P., and Xin T. J. Med. Chem. 39 (1996) 436-445
6. Choi D.R., Shin J.H., Yang J., Yoon S.Y., and Jung Y.H. Bioorg. Med. Chem. Lett. 14 (2004) 1273-1277
7. Bryskier A., and Chantot J.F. Drugs 49 Suppl. 2 (1995) 16-28
8. Koga H., Itoh A., Murayama S., Suzue S., and Irikura T. J. Med. Chem. 23 (1980) 1358-1363
9. Domagala J.M. J. Antimicrob. Chemother. 33 (1994) 685-706
10. Dang Z., Yang Y.S., Ji R.Y., and Zhang S.H. Bioorg. Med. Chem. Lett. 17 (2007) 4523-4526
11. Suto M.J., Domagala J.M., Roland G.E., Mailloux G.B., and Cohen M.A. J. Med. Chem. 35 (1992) 4745-4750
12. Yun H.J., Min Y.H., Lim J.A., Kang J.W., Kim S.Y., Kim M.J., Jeong J.H., Choi Y.J., Kwon H.J., Jung Y.H., Shim M.J., and Choi E.C. Antimicrob. Agents Chemother. 46 (2002) 3071-3074
13. Wang X.Y., Guo Q., Wang Y.C., Liu B.Q., Liu M.L., Sun L.Y., and Guo H.Y. Acta Pharm. Sin. 43 (2008) 819-827
14. Bonjoch J., Inares A., Guardià M., and Bosch J. Heterocycles 26 (1987) 2165-2174
15. Almond M.R., Stimmel J.B., Thompson E.A., and Loudon G.M. Org. Synth. 8 (1993) 132-137
16. Hong C.Y., Kim Y.K., Chang J.H., Kim S.H., Choi H., Nam D.H., Kim Y.Z., and Kwak J.H. J. Med. Chem. 40 (1997) 3584-3593
17. Huang S., Xie R.G., and Tian B.Z. Organic Synthesis Reagent Preparation Manual [M] (1988), Sichuan University Press p. 443
18. N. Takagi, H. Fubasami, H. Matukubo, EP 464823, 1992;
19. Chem. Abstr. 116 (1992) 152003e
20. MICs were determined as described by the NCCLS (see:. National Committee for Clinical Laboratory Standards. Performance Standards for Antimicrobial Susceptibility Testing: 11th Informational Supplement vol. 21 (2001), National Committee for Clinical Laboratory Standards, Wayne, PA M100-S11. The MIC was defined as the lowest concentration of each compound resulting in inhibition of visible growth of bacteria after incubation at 35 °C for 18-24 h