Journal article
Synthesis and evaluation of 1-cyclopropyl-2-thioalkyl-8-methoxy fluoroquinolones
Bioorganic & medicinal chemistry letters, Vol.21(15), pp.4585-4588
2011
DOI: 10.1016/j.bmcl.2011.05.112
PMCID: PMC3138821
PMID: 21705218
Abstract
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.
Details
- Title: Subtitle
- Synthesis and evaluation of 1-cyclopropyl-2-thioalkyl-8-methoxy fluoroquinolones
- Creators
- Kevin R. Marks - University of IowaMuhammad Malik - Public Health Research Institute, New Jersey Medical School, UMDNJ, 225 Warren St., Newark, NJ 07103, USAArkady Mustaev - Public Health Research Institute, New Jersey Medical School, UMDNJ, 225 Warren St., Newark, NJ 07103, USAHiroshi Hiasa - University of MinnesotaKarl Drlica - Public Health Research Institute, New Jersey Medical School, UMDNJ, 225 Warren St., Newark, NJ 07103, USARobert J. Kerns - Division of Medicinal and Natural Products Chemistry, University of Iowa College of Pharmacy, Iowa City, IA 52242, USA
- Resource Type
- Journal article
- Publication Details
- Bioorganic & medicinal chemistry letters, Vol.21(15), pp.4585-4588
- Publisher
- Elsevier Ltd
- DOI
- 10.1016/j.bmcl.2011.05.112
- PMID
- 21705218
- PMCID
- PMC3138821
- ISSN
- 0960-894X
- eISSN
- 1464-3405
- Language
- English
- Date published
- 2011
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
- Record Identifier
- 9984365883402771
Metrics
12 Record Views