Using Bioisosteric Replacements to Enhance the Analgesic Properties of 4-Hydroxy-6,7-Dimethoxy-2-oxo-1,2-Dihydroquinoline-3-Carboxamides
1
National University of Pharmacy, Kharkiv, Ukraine
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2
Chemical Technologies Institute, Vladimir Dahl East Ukrainian National University, Rubizhne, Ukraine
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3
N. I. Pirogov Vinnitsa National Medical University, Vinnitsa, Ukraine
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Publication type: Journal Article
Publication date: 2016-09-01
scimago Q4
wos Q4
SJR: 0.219
CiteScore: 1.4
Impact factor: 1.0
ISSN: 0091150X, 15739031
Drug Discovery
Pharmacology
Abstract
Guided by bioisosteric replacement principles, a series of new N-(hetarylmethyl)-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxamides were synthesized. Pharmacological tests showed that replacement of the benzyl phenyl ring in N-benzyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxamides by an isosteric heterocycle led to a noticeable increase in the analgesic activity only for the 3-Py derivative. The corresponding isomeric 2- and 4-Py derivatives were close to the benzylamide baseline level of analgesic properties whereas the furan, tetrahydrofuran, and thiophene analogs were characterized by a significant decrease in the analgesic activity.
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Ukrainets I. V., Mospanova E. V., Davidenko A. A. Using Bioisosteric Replacements to Enhance the Analgesic Properties of 4-Hydroxy-6,7-Dimethoxy-2-oxo-1,2-Dihydroquinoline-3-Carboxamides // Pharmaceutical Chemistry Journal. 2016. Vol. 50. No. 6. pp. 365-368.
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Ukrainets I. V., Mospanova E. V., Davidenko A. A. Using Bioisosteric Replacements to Enhance the Analgesic Properties of 4-Hydroxy-6,7-Dimethoxy-2-oxo-1,2-Dihydroquinoline-3-Carboxamides // Pharmaceutical Chemistry Journal. 2016. Vol. 50. No. 6. pp. 365-368.
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TY - JOUR
DO - 10.1007/s11094-016-1453-7
UR - https://doi.org/10.1007/s11094-016-1453-7
TI - Using Bioisosteric Replacements to Enhance the Analgesic Properties of 4-Hydroxy-6,7-Dimethoxy-2-oxo-1,2-Dihydroquinoline-3-Carboxamides
T2 - Pharmaceutical Chemistry Journal
AU - Ukrainets, I V
AU - Mospanova, E V
AU - Davidenko, A A
PY - 2016
DA - 2016/09/01
PB - Springer Nature
SP - 365-368
IS - 6
VL - 50
SN - 0091-150X
SN - 1573-9031
ER -
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@article{2016_Ukrainets,
author = {I V Ukrainets and E V Mospanova and A A Davidenko},
title = {Using Bioisosteric Replacements to Enhance the Analgesic Properties of 4-Hydroxy-6,7-Dimethoxy-2-oxo-1,2-Dihydroquinoline-3-Carboxamides},
journal = {Pharmaceutical Chemistry Journal},
year = {2016},
volume = {50},
publisher = {Springer Nature},
month = {sep},
url = {https://doi.org/10.1007/s11094-016-1453-7},
number = {6},
pages = {365--368},
doi = {10.1007/s11094-016-1453-7}
}
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Ukrainets, I. V., et al. “Using Bioisosteric Replacements to Enhance the Analgesic Properties of 4-Hydroxy-6,7-Dimethoxy-2-oxo-1,2-Dihydroquinoline-3-Carboxamides.” Pharmaceutical Chemistry Journal, vol. 50, no. 6, Sep. 2016, pp. 365-368. https://doi.org/10.1007/s11094-016-1453-7.