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Synthesis, spectroscopic, and X-ray structural characterization of pharmacologically active substituted pyrazolyl-acetanilides

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Abstract

Five new pyrazole acetanilides were synthesized by N-alkylation of pyrazole and its derivatives with 4′-propionyl-2-iodoacetanilide. Compounds 1–5 were characterized by 1H NMR, 13C NMR, IR, UV–Vis, MS, and elemental analysis. X-ray structures of representative compounds 1, 3, and 5 established their conformations and solid-state hydrogen bonding preferences. Acute toxicity, local anesthetic, and antiarrhythmic activities were assessed for compounds 1–5 using established protocols. Lower potencies and lower acute toxicities were recorded relative to lidocaine. Enhanced anesthetic activity of compound 3 was attributed to the presence of the propionyl group in the molecule.

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Acknowledgment

MRC thanks the University of Cape Town and the NRF (Pretoria) for research support.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, University of Bucharest, 90-92 Panduri Road, Bucharest, Romania

    Christina Zalaru

  2. Department of Chemistry, University of Cape Town, Rondebosch, 7701, South Africa

    Mino R. Caira

  3. Institute of Organic Chemistry “C.D. Nenitzescu”, Romanian Academy, 202B Spl. Independentei, Bucharest, Romania

    Florea Dumitrascu & Constantin Draghici

  4. Clinical and Sanitary Chemistry Laboratories, University of Medicine and Pharmaceutics “Carol Davila”, 6-Traian Vuia St., Bucharest, Romania

    Elena Cristea

Authors
  1. Christina Zalaru
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  2. Mino R. Caira
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  3. Florea Dumitrascu
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  4. Constantin Draghici
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  5. Elena Cristea
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Corresponding author

Correspondence to Mino R. Caira.

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Zalaru, C., Caira, M.R., Dumitrascu, F. et al. Synthesis, spectroscopic, and X-ray structural characterization of pharmacologically active substituted pyrazolyl-acetanilides. Struct Chem 20, 377–385 (2009). https://doi.org/10.1007/s11224-009-9407-2

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  • DOI: https://doi.org/10.1007/s11224-009-9407-2

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