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Synthesis of eperezolid-like molecules and evaluation of their antimicrobial activities

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Abstract

3-Fluoro-4-(4-phenylpiperazin-l-yl)aniline (II) prepared from 3,4-difluoro nitrobenzene was converted to the corresponding Schiff bases (III) and (IV) by treatment with 4-methoxybenzaldehyde and indol-3-carbaldehyde, respectively. Treatment of amine (II) with 4-fluorophenyl isothiocyanate afforded the corresponding thiourea derivative (V). Compound (V) was converted to thiazolidinone and thiazoline derivatives (VI) and (VII) by cyclocondensation with ethylbromoacetate or 4-chlorophenacylbromide, respectively. The synthesis of carbothioamide derivative (X) was performed starting from compound (II) by three steps. Treatment of compound (X) with sodium hydroxide, sulfuric acid, or chlorophenacyl bromide generated the corresponding 1,2,4-triazole (XI), 1,3,4-thiadiazole (XII), and 1,3-thiazolidinone (XIII) derivatives, respectively. The structural assignments of new compounds were based on their elemental analysis and spectral (IR, 1H-NMR, 13C-NMR, and LC-MS) data. In the antimicrobial activity study all the compounds revealed high anti-Mycobacterium smegmatis activity.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Karadeniz Technical University, Trabzon, Turkey

    Meltem Yolal, Serap Basoglu & Serpil Demirci

  2. Department of Chemistry, Giresun University, Giresun, Turkey

    Hakan Bektas & Ahmet Demirbas

  3. Department of Biology, Rize University, Rize, Turkey

    Sengul Alpay-Karaoglu

Authors
  1. Meltem Yolal
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  2. Serap Basoglu
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  3. Hakan Bektas
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  4. Serpil Demirci
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  5. Sengul Alpay-Karaoglu
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  6. Ahmet Demirbas
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Correspondence to Ahmet Demirbas.

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Yolal, M., Basoglu, S., Bektas, H. et al. Synthesis of eperezolid-like molecules and evaluation of their antimicrobial activities. Russ J Bioorg Chem 38, 539–549 (2012). https://doi.org/10.1134/S106816201205010X

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  • DOI: https://doi.org/10.1134/S106816201205010X

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