Synthesis and Analgesic Activity of N-(1-Aryl-3-oxo-2-azaspiro[3.5]nonan-2-yl)benzamides

被引：2
|
作者：
Nikiforova, E. A. [1 ]
Makhmudov, R. R. [1 ,2 ]
Zverev, D. P. [1 ]
Dmitriev, M. V. [1 ]
Shurov, S. N. [1 ]
Kirillov, N. F. [1 ]
机构：
[1] Perm State Natl Res Univ, Perm 614990, Russia
[2] Fed Sci Ctr Med & Prevent Hlth Risk Management Tec, Perm 614045, Russia
来源：
RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2023年 / 93卷 / 08期
关键词：
Reformatsky reaction; alicyclic Reformatsky reagents; azetidinone; benzoyl hydrazide; aryl methylidene hydrazide; antinociceptive activity; REFORMATSKY REACTION; BETA-LACTAMS;
D O I：
10.1134/S1070363223080029
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The Reformatsky reagent, derived from the methyl 1-bromocyclohexanecarboxylate and zinc, reacts with N'-(arylmethylidene)benzohydrazides, to form N-(1-aryl-3-oxo-2-azaspiro[3.5]nonan-2-yl)benzamides as a result of intramolecular cyclization of the initial addition products. Structure of the prepared benzamides was proved by single crystal X-ray diffraction analysis. In the case of p-tolualdehyde benzoylhydrazone, the adduct of the Reformatsky reagent to the double carbon-nitrogen bond of the substrate, which not underwent cyclization, was predominantly isolated. The resulting spiroazetidin-2-ones exhibit antinociceptive activity.
引用
收藏
页码：1941 / 1950
页数：10
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