Chemical properties of 3-(5-amino-1H-1,2,4-triazol-1-yl)- and 3-(2-amino-1H-benzo[d]imidazol-1-yl)-3-phenylpropanehydrazides

N. V. Svitlichna, O. O. Shishkina, V. V. Borodina, F. G. Yaremenko, V. V. Lipson, V. I. Musatov, V. M. Bondarenko

Abstract


Reactions of 3-(5-amino-1H-1,2,4-triazol-1-yl)- and 3-(2-amіno-1H-benzo[d]іmіdazol-1-yl)-3-phenylpropanehydrazides with carbonyl electrophiles such as acetylacetone, aromatic and heterocyclic aldehydes in the alcoholic medium complete by formation of the corresponding hydrazones as a E-geometric isomers and s-trans/cis conformers with respect to the amide bond. In more severe conditions elimination of hydrazone fragments and retrocondensation of aminoazolophenylpropionyl residues in dihydroazolopyrimidinones have been observed.
The composition and structure of the hydrazones synthesized for the first time have been proven by data of elemental analysis, infrared spectroscopy (IR), nuclear magnetic resonance on protones (1H NMR) and mass spectra.
Virtual screening of the substances obtained carried out by using the PASS programme for 780 types of pharmacological action has shown that these compounds are advisable to test for the presence of their antibacterial and fungicidal properties. However, the experimental evaluation of the antimicrobial activity of N1-ylidene derivatives of 3-phenylpropanehydrazides performed on five museum strains of test cultures has revealed a weak activity against Staphylococcus aureus only in 3-(5-amіno-1H-1,2,4-triazol-1-yl)-N1 benzilіdene-3-phenylpropanehydrazide.


Keywords


dihydro-7-phenyl-1,2,4-triazolo[1,5-a]pyrimіdin-5-one; dihydro-4-phenylpyrimіdo[1,2-a]benzіmіdazol- 2-one; hydrazinolysis; 3-(5-amіno-1,2,4-triazolyl)-3-phenylpropanehydrazide; 3-(2-amіnobenzo[d]іmіdazolyl)- 3-phenylpropanehydrazide; chemical properties;

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DOI: https://doi.org/10.24959/ophcj.14.806

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