Karpenko Y. Synthesis and properties of new 10-((1,3,4-oxadiazol-2-yl)methyl)acridine-9(10H)-ones

The results of kinetic studies of the reaction of liquid-phase hydrazinolysis of butyl ethers were obtained, which allowed us to establish the reaction mechanism. The reactions of hydrazides 2-(2-R-9-oxoacridine-10(9H)-yl)acetate acid with carboxylic acid chlorides and their subsequent heterocyclization, carbon disulfide, methanoic acid, trietilformiat are investigated. There have been developed methods for the preparation of initial functional 1,2-diacylhydrazines with varying solvents and the tertiary base, as well as the conditions for their cyclodehydration. There have been developed preparative methods for the synthesis of functional derivatives at the second position of the 1,3,4-oxadiazole moiety. Thione-thiol tautomerism of new hybrids of 1,3,4-oxadiazole-2(3H)-thiones with acridine-9(10H)-one fragment was studied in solvents with different polarity and dielectric perception. The luminescent characteristics of the synthesized compounds were studied for the first time. Studies of the lipophilicity index by various chromatographic methods (thin-layer, gas and high-performance liquid chromatography), the n-octanol/water distribution method in the binary system and computer-based methods are proposed, and QSAR-models of acute toxicity are constructed. Chemical synthesis, TLC, GC, UV-, IR- and NMR-spectroscopy (1H, 13C), chromatography-mass spectrometry, elemental analysis. Preliminary biological studies of a number of synthesized substances were performed. There were found substances with high affinity for DNA, low toxicity and antimicrobial and diuretic activities. Scope - bioorganic chemistry.