The study is dedicated to the investigation of the stereochemistry and regioselectivity of the formation of compounds in the reactions of the 1,3-dipolar cycloaddition of azomethine ylides, derived from isatins and cyclic and aliphatic α-aminoacids, to the N-substituted maleimides and derivatives of acrylic and metacrylic acids, aroylacrylic and arylmethylidenpyruvic acids and reactions of 2-amino-4-arylimidazoles with acyclic methylene active and carbonyl compounds.
1,3-Dipolar cycloaddition reactions of azomethine ylides, based on isatins and ali-phatic α-aminoacids, with N-substituted maleimides lead to the formation of two enantiomeric spiro[indol-3,1’ pyrrolo[3,4 с]pyrrol]-2,4’,6’-(1H,3’H,5’H)-trions with cis- configuration of the 3а’ and 6а’ protons of the pyrrol[3,4-с]pyrrol system. In alkylation, nitrosation, and acylation reactions of spiro[indol-3,1’ pyrrolo[3,4 с]pyrrol]-2,4’,6’-(1H,3’H,5’H)-trions it may be stated that the primary target of electrophilic attack is the N-2' nitrogen atom of the pyrrolidine ring.
2-Oxospiro(indol-3-pyrrolidine)-, -pyrrolizine- and –pyrrolo[1,2 c]thiazolcarboxamides are regioselectivly formed in cyclocondensations of aroylacrylic and arylmethylidenpyruvic acids and amides and nitriles of acrylic and metacrylic acids with the 2-oxindole azomethine ylides.
Domino reactions of 2-amino-4-arylimidazoles with carbonyl compounds and aliphatic СН-acids (malononitrile, ethyl 2-cyanoacetate, 2-cyanocarboxamide) go through the С5 nucleophilic center in the aminoazole molecule. In case of application of isatin as the carbonyl component of reaction formation of the 6’-substituted 3’,5’-diamino-1-alkyl-2-oxo-1’-arylspiro[indolin-3,7’-pyrrolo[1,2-c]imidazoles] takes place. These compounds can be considered as the analogs of alkaloids with 3,3’-spiroxindole core.
The virtual screening of the novel compounds as the potential inhibitors of the 11β-HSD1 enzyme – the promising target for the developing of antidiabetic remedies – was provided by applying the method of the molecular docking. Antioxidant properties and the complex antidiabetic effect have been experimentally detected for the compound 5е using the model of diabetes mellitus type 2 in rats.
