Synthesis of new 4,4-spirocycloalkenic 1,2-diphenylpyrazolidine-3,5-dione derivatives by ring-closing metathesis reactions

V. M. Holovatiuk, Yu. V. Bezugly, V. I. Kashkovsky

Abstract


The present article describes the synthesis of new 4,4-spiroalkenic 1,2-diarylpyrazolidine-3,5-diones by ring-closing metathesis reactions (RCM). They may be potential biological active compounds since a great quantity of 1,2-diazoles show a wide spectrum of both biological and pharmacological activities, and therefore, they are successfully used in biology, medicine, veterinary medicine. The initial compounds for ring closing metathesis cyclization were synthesized by the corresponding hydrazobenzenes condensation with various allylmalonic acid derivatives, whereupon monoallylpyrazolidinediones obtained were alkylated by some halogenoalkenes to form unsaturated disubstituted 1,2-diarylpyrazolidine-3,5-dione with subsequent ring-closing metathesis. The most appropriate catalyst for carrying out the aforementioned conversion appeared to be the ruthenium carbene Grubbs complex of the second generation used in the concentration not more than 3 mol.%. The yield of the metathesis products was 75-91%. The preliminary computer prognosis of the biological activity of the new spirocycloalkenic 1,2-diazoles by means of Prediction of Activity Spectra for Substances programme has shown that the substances obtained with the high probability may be inhibitors of L-glutamate oxidase and testosterone 17-beta-dehydrogenase (NADP+), nicotine 2alpha2beta receptor antagonists, as well as they can have the anti-inflammatory properties.


Keywords


ruthenium carbene catalysts; metathesis reactions; ring-closing methathesis (RCM); pyrazolidine- 3,5-diones; 1,2-diazolidines; biological activity

GOST Style Citations






DOI: https://doi.org/10.24959/ophcj.14.803

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This work is licensed under a Creative Commons Attribution 4.0 International License.

Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)