Synthesis, spectroscopic, and X-ray structural characterization of pharmacologically active substituted pyrazolyl-acetanilides |
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| Authors: | Christina Zalaru Mino R. Caira Florea Dumitrascu Constantin Draghici Elena Cristea |
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| Affiliation: | (1) Department of Organic Chemistry, Faculty of Chemistry, University of Bucharest, 90-92 Panduri Road, Bucharest, Romania;(2) Department of Chemistry, University of Cape Town, Rondebosch, 7701, South Africa;(3) Institute of Organic Chemistry “C.D. Nenitzescu”, Romanian Academy, 202B Spl. Independentei, Bucharest, Romania;(4) Clinical and Sanitary Chemistry Laboratories, University of Medicine and Pharmaceutics “Carol Davila”, 6-Traian Vuia St., Bucharest, Romania |
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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. Electronic supplementary material The online version of this article (doi:) contains supplementary material, which is available to authorized users. |
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| Keywords: | Local anesthetics Synthesis X-ray structures Hydrogen bonding Pharmacological activities |
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