On the binding site of quinolone antibacterials. An attempt to probe the Shen model

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 19, 1996, Pages 2333-2338

  Hanessian, Stephen ^a   Saladino, Raffaele ^a   Nunez, Jose Cid ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE DERIVED ANTIINFECTIVE AGENT;

ANTIBACTERIAL ACTIVITY; ARTICLE; DNA BINDING; IN VITRO STUDY; MODEL; REACTION ANALYSIS;

EID: 0030575608     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00430-1     Document Type: Article

References (28)

1. 1. For a selection of monographs, see Siporin, C.; Heifetz, C. L.; Domagala, J.-M. In The New Generation of Quinolones; M. Dekker: New York, 1990; Crumplin, G. C. In The 4-Quinolones: Antibacterial Agents in Vitro; Springer Verlag: New York, 1990; Andriole, V. T. In The Quinolones; Academic: New York, 1989; Wolfson, J. S.; Hooper, D. C. In Quinolone Antimicrobial Agents; American Society for Microbiology, Washington, D.C 1989; Fernandez, P. B. Ed.; Int. Telesymposium of Quinolones, J. R. Prous, Barcelona, Spain; for recent reviews, see Domagala, J. M. J. Antimicrob. Chemother 1994, 33, 685; Hammond, M. L. Ann. Rep. Med. Chem. 1993, 25, 119.
2. 1. For a selection of monographs, see Siporin, C.; Heifetz, C. L.; Domagala, J.-M. In The New Generation of Quinolones; M. Dekker: New York, 1990; Crumplin, G. C. In The 4-Quinolones: Antibacterial Agents in Vitro; Springer Verlag: New York, 1990; Andriole, V. T. In The Quinolones; Academic: New York, 1989; Wolfson, J. S.; Hooper, D. C. In Quinolone Antimicrobial Agents; American Society for Microbiology, Washington, D.C 1989; Fernandez, P. B. Ed.; Int. Telesymposium of Quinolones, J. R. Prous, Barcelona, Spain; for recent reviews, see Domagala, J. M. J. Antimicrob. Chemother 1994, 33, 685; Hammond, M. L. Ann. Rep. Med. Chem. 1993, 25, 119.
3. 1. For a selection of monographs, see Siporin, C.; Heifetz, C. L.; Domagala, J.-M. In The New Generation of Quinolones; M. Dekker: New York, 1990; Crumplin, G. C. In The 4-Quinolones: Antibacterial Agents in Vitro; Springer Verlag: New York, 1990; Andriole, V. T. In The Quinolones; Academic: New York, 1989; Wolfson, J. S.; Hooper, D. C. In Quinolone Antimicrobial Agents; American Society for Microbiology, Washington, D.C 1989; Fernandez, P. B. Ed.; Int. Telesymposium of Quinolones, J. R. Prous, Barcelona, Spain; for recent reviews, see Domagala, J. M. J. Antimicrob. Chemother 1994, 33, 685; Hammond, M. L. Ann. Rep. Med. Chem. 1993, 25, 119.
4. 1. For a selection of monographs, see Siporin, C.; Heifetz, C. L.; Domagala, J.-M. In The New Generation of Quinolones; M. Dekker: New York, 1990; Crumplin, G. C. In The 4-Quinolones: Antibacterial Agents in Vitro; Springer Verlag: New York, 1990; Andriole, V. T. In The Quinolones; Academic: New York, 1989; Wolfson, J. S.; Hooper, D. C. In Quinolone Antimicrobial Agents; American Society for Microbiology, Washington, D.C 1989; Fernandez, P. B. Ed.; Int. Telesymposium of Quinolones, J. R. Prous, Barcelona, Spain; for recent reviews, see Domagala, J. M. J. Antimicrob. Chemother 1994, 33, 685; Hammond, M. L. Ann. Rep. Med. Chem. 1993, 25, 119.
5. 1. For a selection of monographs, see Siporin, C.; Heifetz, C. L.; Domagala, J.-M. In The New Generation of Quinolones; M. Dekker: New York, 1990; Crumplin, G. C. In The 4-Quinolones: Antibacterial Agents in Vitro; Springer Verlag: New York, 1990; Andriole, V. T. In The Quinolones; Academic: New York, 1989; Wolfson, J. S.; Hooper, D. C. In Quinolone Antimicrobial Agents; American Society for Microbiology, Washington, D.C 1989; Fernandez, P. B. Ed.; Int. Telesymposium of Quinolones, J. R. Prous, Barcelona, Spain; for recent reviews, see Domagala, J. M. J. Antimicrob. Chemother 1994, 33, 685; Hammond, M. L. Ann. Rep. Med. Chem. 1993, 25, 119.
6. 1. For a selection of monographs, see Siporin, C.; Heifetz, C. L.; Domagala, J.-M. In The New Generation of Quinolones; M. Dekker: New York, 1990; Crumplin, G. C. In The 4-Quinolones: Antibacterial Agents in Vitro; Springer Verlag: New York, 1990; Andriole, V. T. In The Quinolones; Academic: New York, 1989; Wolfson, J. S.; Hooper, D. C. In Quinolone Antimicrobial Agents; American Society for Microbiology, Washington, D.C 1989; Fernandez, P. B. Ed.; Int. Telesymposium of Quinolones, J. R. Prous, Barcelona, Spain; for recent reviews, see Domagala, J. M. J. Antimicrob. Chemother 1994, 33, 685; Hammond, M. L. Ann. Rep. Med. Chem. 1993, 25, 119.
7. 1. For a selection of monographs, see Siporin, C.; Heifetz, C. L.; Domagala, J.-M. In The New Generation of Quinolones; M. Dekker: New York, 1990; Crumplin, G. C. In The 4-Quinolones: Antibacterial Agents in Vitro; Springer Verlag: New York, 1990; Andriole, V. T. In The Quinolones; Academic: New York, 1989; Wolfson, J. S.; Hooper, D. C. In Quinolone Antimicrobial Agents; American Society for Microbiology, Washington, D.C 1989; Fernandez, P. B. Ed.; Int. Telesymposium of Quinolones, J. R. Prous, Barcelona, Spain; for recent reviews, see Domagala, J. M. J. Antimicrob. Chemother 1994, 33, 685; Hammond, M. L. Ann. Rep. Med. Chem. 1993, 25, 119.
8. 2. See for examples, such classes as macrolides, tetracyclines, β-lactams, In Emerging Targets in Antibacterial and Antifungal Chemotherapy; Sutcliffe, J.; Georgopapadakou, N. Eds.; Chapman and Hall: New York, 1992; Antibiotics and Antiviral Compounds. Chemical Synthesis and Modifications; Krohn, K.; Kirst, H. A.; Maag, H.; Eds; VCH: New York, 1993.
9. 2. See for examples, such classes as macrolides, tetracyclines, β-lactams, In Emerging Targets in Antibacterial and Antifungal Chemotherapy; Sutcliffe, J.; Georgopapadakou, N. Eds.; Chapman and Hall: New York, 1992; Antibiotics and Antiviral Compounds. Chemical Synthesis and Modifications; Krohn, K.; Kirst, H. A.; Maag, H.; Eds; VCH: New York, 1993.
10. For a recent review, see Shen, L. L. Adv. Pharmacol. 1994, 29A, 285; and references cited therein; Reece, R. J.; Maxwell, A. CRC-Critical Rev. Biochem. Mol. Biol. 1991, 26, 335.
11. For a recent review, see Shen, L. L. Adv. Pharmacol. 1994, 29A, 285; and references cited therein; Reece, R. J.; Maxwell, A. CRC-Critical Rev. Biochem. Mol. Biol. 1991, 26, 335.
12. 4. For recent discussions, see Shen, L. L. In Molecular Biology of DNA Topoisomerases and its Application to Chemotherapy, Andoh, T.; Ikeda, H.; Oguro, M. Eds.; CRC: Ann Arbor, 1993; p 177; Shen, L. L. In Quinolone Antimicrobial Agents, Hooper, D. C.; Wolfson, J. S., Eds; American Society of Microbiology, Washington, D.C., 1993; p 11.
13. 4. For recent discussions, see Shen, L. L. In Molecular Biology of DNA Topoisomerases and its Application to Chemotherapy, Andoh, T.; Ikeda, H.; Oguro, M. Eds.; CRC: Ann Arbor, 1993; p 177; Shen, L. L. In Quinolone Antimicrobial Agents, Hooper, D. C.; Wolfson, J. S., Eds; American Society of Microbiology, Washington, D.C., 1993; p 11.
14. 5. Shen, L. L.; Mitscher, L. A.; Sharma, P. N.; O'Donnell, T. J.; Chu, D. T. W.; Cooper, C. S.; Rosen, T.; Pernet, A. G. Biochem. 1989, 28, 3886.
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23. 13C NMR spectroscopy, by HRMS and microanalytical data when possible.
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28. 2, EtOH, 90%; (e) condensation according to Scheme 1.