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Synthesis, Hydrolysis, and Analgesic Activity of 3-[3-(1-arylethylcarbamoyl)-4-hydroxy-2-oxo-1,2-dihydroquinolin-1-yl]propanenitriles and Their Derivatives

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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.

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Authors and Affiliations

  1. National Pharmaceutical University, Kharkov, Ukraine

    I. V. Ukrainets, E. A. Taran & K. V. Andreeva

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  1. I. V. Ukrainets
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  2. E. A. Taran
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  3. K. V. Andreeva
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 50, No. 7, pp. 9 – 13, July, 2016.

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Ukrainets, I.V., Taran, E.A. & Andreeva, K.V. Synthesis, Hydrolysis, and Analgesic Activity of 3-[3-(1-arylethylcarbamoyl)-4-hydroxy-2-oxo-1,2-dihydroquinolin-1-yl]propanenitriles and Their Derivatives. Pharm Chem J 50, 431–435 (2016). https://doi.org/10.1007/s11094-016-1464-4

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  • DOI: https://doi.org/10.1007/s11094-016-1464-4

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