SUBSTITUTED 4-NITROSOPYRAZOLES IN THE DIELS-ALDER REACTION
2021
Darya S. Volkova | Arkadiy A. Popov | Evgeny V. Root | Alexey A. Kukushkin | George A. Suboch
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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