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

Gavara Govinda Rajulu; Halehatty Seephya Bhojya Naik; Abhilash Viswanadhan; Jayaraman Thiruvengadam; Kondodiyil Rajesh; Sambasivam Ganesh; Hiriyan Jagadheshan; Poonimangadu Koppolu Kesavan

doi:10.1248/cpb.c13-00797

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

Gavara Govinda Rajulu , Halehatty Seephya Bhojya Naik, Abhilash Viswanadhan, Jayaraman Thiruvengadam, Kondodiyil Rajesh, Sambasivam Ganesh, Hiriyan Jagadheshan, Poonimangadu Koppolu Kesavan

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Keywords: fluoroquinolone, hydroxamic acid, [1,2,3]triazolyl derivative, antibacterial activity, anticancer activity

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2014 Volume 62 Issue 2 Pages 168-175

DOI https://doi.org/10.1248/cpb.c13-00797

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Abstract

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.

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