New Hydroxamic Acid Derivatives of Fluoroquinolones: Synthesis and Evaluation of Antibacterial and Anticancer Properties

A series of new hydroxamic acid derivatives (6a–f) at C-3 position of fluoroquinolones were designed and synthesized through multistep synthesis. The design concept involved replacement of the 3-carboxylic acid in fluoquinolones with hydroxamic acid as an acid mimicking group. The synthetic work emp...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 2014/02/01, Vol.62(2), pp.168-175
Hauptverfasser: Rajulu, Gavara Govinda, Naik, Halehatty Seephya Bhojya, Viswanadhan, Abhilash, Thiruvengadam, Jayaraman, Rajesh, Kondodiyil, Ganesh, Sambasivam, Jagadheshan, Hiriyan, Kesavan, Poonimangadu Koppolu
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Sprache:eng
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Zusammenfassung:A series of new hydroxamic acid derivatives (6a–f) at C-3 position of fluoroquinolones were designed and synthesized through multistep synthesis. The design concept involved replacement of the 3-carboxylic acid in fluoquinolones with hydroxamic acid as an acid mimicking group. The synthetic work employed in this work provides a good example for the synthesis of pure hydroxamic acid based fluoroquinolones. The synthesized compounds were characterized by 1H-NMR, electrospray ionization (ESI)-MS and IR. The new compounds were tested for their in vitro antimicrobial and anti-proliferative activity. Out of the six derivatives, compound 6e exhibited moderate antibacterial activity by inhibiting the growth of Escherichia coli and Klebsiella pneumoniae (MIC: 4.00–8.00 µg/mL). Compounds 6b and 6f displayed good growth inhibition against A549 Lung adenocarcinoma and HCT-116 Colon carcinoma cell lines.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.c13-00797