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Synthesis and antibacterial activity of 4-benzoyl-1-(4-carboxy-phenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid and derivatives

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Abstract

A new 1H-pyrazole-3-carboxylic acid 2, along with hydrazono-pyridazinone 3, a by-product, and its derivatives 4–7 were synthesized and the structures confirmed by infrared (IR) and 1H and 13C nuclear magnetic resonance (NMR) data. These new compounds were evaluated for their antibacterial activities against Gram-positive and Gram-negative bacteria using the tube dilution method. The minimal inhibitory concentrations (MICs) experiments revealed that most compounds exerted inhibitor effects against Klebsiella pneumonia, Escherichia coli, Bacillus subtilus, and Xanthomonas compestris test microorganisms. Moreover, the results showed that the pyrazolo[3,4-d]pyridazine compounds were the best compounds of the series, exhibiting antibacterial activity against both Gram-positive and Gram-negative bacteria.

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Authors and Affiliations

  1. Organic Chemistry Division, Chemistry Department, Faculty of Arts and Sciences, Yüzüncü Yıl University, 65080, Van, Turkey

    İshak Bildirici, Ahmet Şener & Hasan Genç

  2. Molecular Biology Division, Biology Department, Faculty of Arts and Sciences, Yüzüncü Yıl University, 65080, Van, Turkey

    Ekrem Atalan & Abdulhamit Battal

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  1. İshak Bildirici
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  2. Ahmet Şener
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  3. Ekrem Atalan
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  4. Abdulhamit Battal
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  5. Hasan Genç
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Correspondence to İshak Bildirici.

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Bildirici, İ., Şener, A., Atalan, E. et al. Synthesis and antibacterial activity of 4-benzoyl-1-(4-carboxy-phenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid and derivatives. Med Chem Res 18, 327–340 (2009). https://doi.org/10.1007/s00044-008-9130-3

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