Synthesis, Hydrolysis, and Analgesic Activity of 3-[3-(1-arylethylcarbamoyl)-4-hydroxy-2-oxo-1,2-dihydroquinolin-1-yl]propanenitriles and Their Derivatives
- Authors: Ukrainets I.V.1, Taran E.A.1, Andreeva K.V.1
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Affiliations:
- National Pharmaceutical University
- Issue: Vol 50, No 7 (2016)
- Pages: 431-435
- Section: Search for New Drugs
- URL: https://journals.rcsi.science/0091-150X/article/view/244411
- DOI: https://doi.org/10.1007/s11094-016-1464-4
- ID: 244411
Cite item
Abstract
X-ray diffraction analysis studies showed that in a mixture of HCl, AcOH, and H2O, hydrolysis of several 3-[3-(1-arylethylcarbamoyl)-4-hydroxy-2-oxo-1,2-dihydroquinolin-1-yl]propanenitriles proceeded by an anomalous pathway to yield 4-hydroxy-1-(2-carboxyethyl)-2-oxo-1,2-dihydroquinoline-3-carboxylic acid. These experiments showed that methylation of the methylene bridge separating the amide nitrogen atom and the aromatic nucleus led to a drop in activity. At the same time, hydration of quinolinylpropanenitriles to the corresponding propanamides was seen as a successful approach to chemical modification enhancing analgesic properties.
About the authors
I. V. Ukrainets
National Pharmaceutical University
Email: chem@folium.ru
Ukraine, Kharkov
E. A. Taran
National Pharmaceutical University
Email: chem@folium.ru
Ukraine, Kharkov
K. V. Andreeva
National Pharmaceutical University
Email: chem@folium.ru
Ukraine, Kharkov