Synthesis, antibacterial, and DNA-PK evaluation of some novel 6-fluoro-7-(cyclic amino)-2-(thioxo or oxo)-3-substituted quinazolin-4-ones as structural analogues of quinolone and quinazolin-2,4-dione antibiotics

Quinolones, isothiazoloquinolone, and quinazolin-2,4-diones represent a series of potent antibacterial agents. In this investigation, a series of novel 6-fluoro-7-(cyclic amino)-1-ethyl-2-(thioxo or oxo)-3-substituted quinazolin-4-ones were synthesized from a 6,7-difluoro-1-ethyl-2-(thioxo or oxo) q...

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Bibliographic Details
Published in:Medicinal chemistry research 2015-06, Vol.24 (6), p.2756-2769
Main Authors: Heppell, Jacob T., Al-Rawi, Jasim M. A.
Format: Article
Language:English
Subjects:
Biochemistry
Biomedical and Life Sciences
Biomedicine
Cell Biology
Original Research
Pharmacology/Toxicology
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Summary:Quinolones, isothiazoloquinolone, and quinazolin-2,4-diones represent a series of potent antibacterial agents. In this investigation, a series of novel 6-fluoro-7-(cyclic amino)-1-ethyl-2-(thioxo or oxo)-3-substituted quinazolin-4-ones were synthesized from a 6,7-difluoro-1-ethyl-2-(thioxo or oxo) quinazolin-4-one parent by esterification or amidification of the 3-NH followed by nucleophilic aromatic substitution of the 7-fluoro atom with cyclic secondary amines. The resulting compounds were subsequently evaluated for antibacterial activity but were inactive against the tested bacterial strains. Nevertheless, moderate activity against DNA-PK was observed at 10 µM for a selection of compounds.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-015-1336-6