Synthesis and evaluation of 1-cyclopropyl-2-thioalkyl-8-methoxy fluoroquinolones

Kevin R. Marks, Muhammad Malik, Arkady Mustaev, Hiroshi Hiasa, Karl Drlica, Robert J. Kerns

Research output: Contribution to journalArticlepeer-review

7 Scopus citations


Novel fluoroquinolone derivatives substituted with a 2-thioalkyl moiety, with and without a concomitant 3-carboxylate group, were synthesized to evaluate the effect of C-2 thioalkyl substituents on gyrase binding and inhibition. The presence of a 2-thioalkyl group universally decreased activity as compared to parent fluoroquinolones. However, with derivatives of moxifloxacin the presence of either a 2-thioalkyl group or a 3-carboxylate moiety increased activity over the 2,3-unsubstituted derivative. Energy minimization of structures provides an explanation for relative activities of fluoroquinolones having a C-2 thio moiety.

Original languageEnglish (US)
Pages (from-to)4585-4588
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Issue number15
StatePublished - Aug 1 2011

Bibliographical note

Funding Information:
This work was supported by NIH Grants R01-AI73491 and R01-AI087671 .


  • Antibacterial
  • DNA gyrase
  • Fluoroquinolone
  • Moxifloxacin
  • Ulifloxacin


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