Using Bioisosteric Replacements to Enhance the Analgesic Properties of 4-Hydroxy-6,7-Dimethoxy-2-oxo-1,2-Dihydroquinoline-3-Carboxamides

被引：5

作者：

Ukrainets, I. V. ^{[1
]}

Mospanova, E. V. ^{[2
]}

Davidenko, A. A. ^{[3
]}

机构：

[1] Natl Univ Pharm, UA-61002 Kharkov, Ukraine

[2] Vladimir Dahl East Ukrainian Natl Univ, Inst Chem Technol, UA-93009 Rubizhne, Lugansk Oblast, Ukraine

[3] NI Pirogov Vinnitsa Natl Med Univ, UA-21000 Vinnitsa, Ukraine

来源：

PHARMACEUTICAL CHEMISTRY JOURNAL | 2016年 / 50卷 / 06期

关键词：

4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides; synthesis; amidation; analgesic activity; bioisosteric replacements; BIOLOGICAL-PROPERTIES;

D O I：

10.1007/s11094-016-1453-7

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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.

引用

页码：365 / 368

页数：4

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