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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Structural Studies on N-(1-naphthyl)-3-amino-5-oxo-4-phenyl-1Hpyrazole- 1-carboxamide with Antibacterial Activity

Author(s): Agnieszka A. Kaczor, Tomasz Wrobel, Zbigniew Karczmarzyk, Waldemar Wysocki, Andrzej Fruzinski, Malgorzata Brodacka, Dariusz Matosiuk and Monika Pitucha

Volume 11, Issue 1, 2014

Page: [40 - 48] Pages: 9

DOI: 10.2174/157017861101140113161101

Price: $65

Abstract

The structure and tautomerism of N-(1-naphthyl)-3-amino-5-oxo-4-phenyl-1H-pyrazole-1-carboxamide with antibacterial activity have been investigated with experimental approaches (X-ray studies, IR, 1H and 13C NMR spectra, including NOESY and N-HSQC spectra) and quantum chemical calculations. It is found that the tautomer with the keto group in position 5 is energetically privileged in the crystalline state while in DMSO and water solution the equilibrium is shifted towards the form with the hydroxyl group at this position. These findings are related to antibacterial activity of the studied compound and are crucial for future molecular docking and structure-activity relationship studies.

Keywords: Antibacterial compounds, pyrazolones, quantum chemical calculations, tautomerism, X-ray structure determination.


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