4-Hydroxy-2-quinolones. 180*. Synthesis,chemical reactions,and analgesic activity of 1-allyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkylamides |
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Authors: | I. V. Ukrainets E. V. Mospanova A. A. Davidenko S. V. Shishkina |
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Affiliation: | (1) National University of Pharmacy, Kharkiv, 61002, Ukraine;(2) Chemical Technology Institute, V. Dal East-Ukrainian National University, Rubizhne, 93003, Ukraine;(3) N. I. Pirogov National Medical University, Vinnitsa, 21018, Ukraine;(4) Institute for Single Crystal, National Academy of Sciences of Ukraine, Kharkiv, 61001, Ukraine |
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Abstract: | A targeted synthesis was carried out of a series of 1-allyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-di-hydroquinoline-3-carboxylic acid alkylamides which show interest for biological study as potential analgesics. It was found that, in the presence of one equivalent of bromine, the compounds indicated undergo halocyclization to the corresponding 2-bromomethyl-7,8-dimethoxy-5-oxo-1,2-dihydro-5H-oxa-zolo[3,2-a]quinoline-4-carboxylic acid alkylamides. However, with an excess of bromine the reaction occurs somewhat differently and concludes with the formation of complexes of bromine with 4-alkyl-carbamoyl-2-bromomethyl-5-hydroxy-7,8-dimethoxy-1,2-dihydrooxazolo[3,2-a]quinolinium ditri- bromides. According to the results of pharmacological screening there are found compounds within the substances discovered with high analgesic activity. |
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