Reconstructive Methodology in the Synthesis of 2-Aminopurine.

A fundamentally new synthetic approach to the synthesis of 2-aminopurine has been developed. It consists in the combination of the creation of a condensed polyazotic heterocyclic tetrazolopyrimidine structure, its transformation into triaminopyrimidine, and its subsequent cyclization into 2-aminopurine. The structure of the obtained compounds was established based on spectral characteristics, and the structure of the intermediate compound 5 was established directly by X-ray diffraction analysis.

CK2 Inhibition and Antitumor Activity of 4,7-Dihydro-6-nitroazolo[1,5-a]pyrimidines.

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.

Oxidative Aromatization of 4,7-Dihydro-6-nitroazolo[1,5-a]pyrimidines: Synthetic Possibilities and Limitations, Mechanism of Destruction, and the Theoretical and Experimental Substantiation.

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.

Benzimidazoazapurines: Design, Synthesis, and Photophysical Study.

A highly efficient approach to a new class of polycyclic 8-azapurines, benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidines (BITPs), with good photophysical characteristics is proposed. The approach comprises condensation of aminobenzimidazoles with 3-oxo-2-phenylazopropionitrile to form 3-(arylazo)benzo[4,5]imidazo[1,2-a]pyrimidine-4-amines, which undergo oxidative cyclization by the catalytic action of copper(II) acetate, resulting in BITPs with 73-84% yield. Spectral investigations demonstrated the fluorescent properties of BITPs, exhibiting good quantum yields (up to 60%) with maxima absorption at 379-399 and emission at 471-505 nm.

Three-Component Coupling of Aromatic Aldehydes, 1-Morpholino-2-nitroalkenes, and 3-Aminoazoles via Boron Trifluoride Etherate Catalysis: Reaction Pathway and Features of the Formation of Intermediates.

4,7-Dihydro-6-nitro-7-Ar-5-R-azolo[1,5-a]pyrimidines were obtained by the multicomponent reaction of aminoazoles, morpholino-nitroalkenes, and aromatic aldehydes in the catalysis of boron trifluoride etherate. The optimal reaction conditions were determined, and the formation of the target regioisomer was demonstrated. The pathway for multicomponent transformation, including the formation of azolyl-nitroalkene, was determined. Morpholino-nitroalkenes were assumed to convert into the corresponding nitroalkynes during catalysis of boron trifluoride etherate. For a multicomponent reaction with 4-nitrobenzaldehyde, conditions have been proposed that exclude the formation of a side regioisomer.