Synthesis and analgesic activity of N-(1-aryl-3-oxo-2-azaspiro[3.5]nonan-2-yl)benzamides

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Abstract

The Reformatsky reagent, derived from the methyl 1-bromocyclohexanecarboxylate and zinc, reacts with N′ -(arylmethylidene)benzohydrazides, to form, as a result of intramolecular cyclization of the initial addition products, N -(1-aryl-3-oxo-2-azaspiro[3.5]nonan-2-yl)benzamides. The structure of the latter was proved by 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.

About the authors

E. A Nikiforova

Perm State National Research University

Email: vikro@ya.ru

R. R Makhmudov

Perm State National Research University;Federal Scientific Center for Medical and Preventive Health Risk Management Technologies

D. P Zverev

Perm State National Research University

M. V Dmitriev

Perm State National Research University

S. N Shurov

Perm State National Research University

N. F Kirillov

Perm State National Research University

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