SUBSTITUTED 4-NITROSOPYRAZOLES IN THE DIELS-ALDER REACTION

Darya S. Volkova; Arkadiy A. Popov; Evgeny V. Root; Alexey A. Kukushkin; George A. Suboch

doi:10.12731/2658-6649-2021-13-5-104-119

Darya S. Volkova Reshetnev Siberian State University of Science and Technology
Arkadiy A. Popov Reshetnev Siberian State University of Science and Technology
Evgeny V. Root Reshetnev Siberian State University of Science and Technology; Krasnoyarsk State Medical University named after Prof. V.F.Voino-Yasenetsky
Alexey A. Kukushkin Reshetnev Siberian State University of Science and Technology
George A. Suboch Reshetnev Siberian State University of Science and Technology

DOI: https://doi.org/10.12731/2658-6649-2021-13-5-104-119

Keywords: nitrosopyrazoles, tetracyclone, Diels-Alder reaction, diene condensation, PASS-online, HPLC/MS, mass-spectrometry

Abstract

Background. 4-Nitrosopyrazoles have become widespread in the pharmaceutical industry and in chemistry due to their high reactivity and biological activity. However, the interaction of 3,5-substituted 4-nitroso-1H-pyrazoles with diene hydrocarbons has not been studied to date.

Purpose. Study of diene condensation of tetraphenylcyclopentadienone with 3,5-dimethyl-4-nitroso-1H-pyrazole and 3(5)-methyl-4-nitroso-5(3)-phenyl-1H-pyrazole; proof of the structure of the obtained compounds; prediction of potential positive biological activity.

Materials and methods. Research methods include: directed organic synthesis, thin-layer chromatography, chromato-mass spectra, prediction of biological activity using the PASS-online web-resource.

Results. Substituted oxazines, pyrazoles and but-2-en-1-ones were synthesized. Fragmentation decays based on the mass spectrum of the obtained compounds confirm their molecular weight and structure. The PASS-online program predicts potential biological activity.

Conclusion. Substituted oxazines, pyrazoles and but-2-en-1-ones were obtained for the first time by the Diels-Alder reaction, the structure of which was proved by HPLC/MS. Based on the output data of the PASS-online program, the synthesized substances are taurine dehydrogenase inhibitors and exhibit antitumor effect.

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Author Biographies

Darya S. Volkova, Reshetnev Siberian State University of Science and Technology

2st year master’s student

Arkadiy A. Popov, Reshetnev Siberian State University of Science and Technology

4th year bachelor’s student

Evgeny V. Root, Reshetnev Siberian State University of Science and Technology; Krasnoyarsk State Medical University named after Prof. V.F.Voino-Yasenetsky

Ph. D., Associate Professor of the Department of Organic Chemistry and Technology of Organic Compounds; Associate Professor of the Department of Pharmacy with РС

Alexey A. Kukushkin, Reshetnev Siberian State University of Science and Technology

Ph. D., Associate Professor of the Department of Organic Chemistry and Technology of Organic Compounds

George A. Suboch, Reshetnev Siberian State University of Science and Technology

Doctor of Sciences, Professor Head of the Department of Organic Chemistry and Technology of Organic Compounds

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