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Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids
Abstract
Previous quantitative and qualitative structure-activity studies in antibacterial monosubstituted 1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids prompted us to synthesize the 6,7,8-polysubstituted compounds. In this paper, the preparation and antibacterial activity of the 6,7- and 7,8-disubstituted compounds and their derivatives are described. Among these compounds, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxylic acid (34) possessed many significant activities and was more active than oxolinic acid (84) against Gram-positive and Gram-negative bacteria. Structure-activity relationships are discussed.
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Cited by
Wang, J., Sánchez-Roselló, M., Aceña, J. L., del Pozo, C., Sorochinsky, A. E., Fustero, S., Soloshonok, V. A., & Liu, H. (2014) · Chemical Reviews · doi:10.1021/cr4002879 · Cited by 4,847
Introduction of Fluorine and Fluorine‐Containing Functional Groups
Liang, T., Neumann, C. N., & Ritter, T. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201206566 · Cited by 2,564
Bacterial Topoisomerase Inhibitors: Quinolone and Pyridone Antibacterial Agents
Mitscher, L. A. (2005) · Chemical Reviews · doi:10.1021/cr030101q · Cited by 781
Wolfson, J. S., & Hooper, D. C. (1985) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.28.4.581 · Cited by 698
Computational methods in drug discovery
Leelananda, S. P., & Lindert, S. (2016) · Beilstein Journal of Organic Chemistry · doi:10.3762/bjoc.12.267 · Cited by 639
Metadata
- Authors
- Koga, H., Itoh, A., Murayama, S., Suzue, S., & Irikura, T.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1980-12
- Volume
- 23
- Issue
- 12
- Pages
- 1358-1363
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2026553441
- Cited by
- 486
- References
- 0
- FWCI
- 4.96
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids. https://app.cochat.ai/papers/10.1021/jm00186a014
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- Koga, H., Itoh, A., Murayama, S., Suzue, S., & Irikura, T. (1980). Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm00186a014
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