The reaction tolerance of the multicomponent process between 3-aminoazoles, 1-morpholino-2-nitroalkenes, and aldehydes was studied. The main patterns of this reaction have been established. Conditions for the oxidation of 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines were selected. Previous claims that the 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines could not be aromatised have now been refuted. Compounds with an electron-donor substituent at position seven undergo decomposition during oxidation. The phenomenon was explained based on experimental data, electro-chemical experiment, and quantum-chemical calculation. The mechanism of oxidative degradation has been proposed.
Today, cancer is one of the most widespread and dangerous human diseases with a high mortality rate. Nevertheless, the search and application of new low-toxic and effective drugs, combined with the timely diagnosis of diseases, makes it possible to cure most types of tumors at an early stage. In this work, the range of new polysubstituted 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines was extended. The structure of all the obtained compounds was confirmed by the data of 1H, 13C NMR spectroscopy, IR spectroscopy, and elemental analysis. These compounds were evaluated against human recombinant CK2 using the ADP-GloTM assay. In addition, the IC50 parameters were calculated based on the results of the MTT test against glioblastoma (A-172), embryonic rhabdomyosarcoma (Rd), osteosarcoma (Hos), and human embryonic kidney (Hek-293) cells. Compounds 5f, 5h, and 5k showed a CK2 inhibitory activity close to the reference molecule (staurosporine). The most potential compound in the MTT test was 5m with an IC50 from 13 to 27 µM. Thus, our results demonstrate that 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines are promising for further investigation of their antitumor properties.
To date, nitro-containing compounds form one of the most important classes of organic compounds. The chemistry of these molecules attracts attention primarily due to their use as high-energy reagents and drugs. Also, the introduction of a nitro group is a popular synthetic strategy for constructing new organic molecules. The present review summarizes the latest research findings of compounds bearing a nitro group on a two-carbon moiety such as aminonitroethylenes, α,α-bis(alkylsulfanyl)nitroalkenes and their amino derivatives, α-nitroketones, alkyl nitroacetates and nitroacetonitrile. The literature data are systematized according to the type of chemical reactions such as reactions between nucleophiles and electrophiles, various cyclization reactions, reactions at the C–H bond, etc. The reactivities of the said nitro compounds and the conditions of chemical transformations are compared to assess the prospects of their application. The bibliography includes 314 references.
1 January 2018 in Chemistry of Heterocyclic Compounds