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Cinnoline Analogs of Quinolones: Structural Consequences of the N Atom Introduction in the Position 2

  • Marek L. Główka
  • Dariusz Martynowski
  • Andrzej Olczak
  • Alina Staszewska

Abstract

According to a mechanism of inhibition of DNA-gyrase complex by quinolones proposed by Shen [I], the drug binds guanine base of a single stranded bacterial DNA. One of the consequences of this model is that binding energy depends on negative partial charges on O(4) and O(3) atoms (Fig.1), i.e. the greater negative charges the stronger will be the hydrogen bonds with guanine. We assume that introduction of N atom(s) into aromatic rings system of quinolones should affect partial charges on the O(4) and O(3). As positions 3,4 and 7 in quinolones are usually substituted, the remaining positions for N substitution are 2,5,6 and 8 (Fig.1). Some of them exert significant effects on structural and electronic properties of the quinolone analogs.

Keywords

Binding Energy Antibacterial Activity Intramolecular Hydrogen Bond Ring System Nalidixic Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    L.S. Shen, L.A. Mitscher, P.N. Sharma, T.J. O’Donnell, D.W.T. Chu, C.S. Cooper, T. Rosen, and A.G. Perret, Mechanism of inhibition of DNA gyrase by quinolone antibacterials: a cooperative drug-DNA binding model, Biochemistry 28: 3886 (1989).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2000

Authors and Affiliations

  • Marek L. Główka
    • 1
  • Dariusz Martynowski
    • 1
  • Andrzej Olczak
    • 1
  • Alina Staszewska
    • 1
  1. 1.Institute of General and Ecological ChemistryTechnical University of ŁódźŁódźPoland

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