Synthesis, computational and biological activity of heteroatomic compounds based on phenylthiourea and acetophenone

The presented article is devoted to a promising direction of organic chemistry - the synthesis of new sulfur- and nitrogen-containing thiourea and acetophenone derivatives that have physiological properties. So at first time on the base of phenylthiourea, acetylacetone and 37% water solution of formaldehyde (formaline) in the presence of trifluoracetic acid has been elaborated new effective synthesic method of 1-(6-Methyl-3-phenyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl)ethanone. Also, according to the reaction of thiylation of acetophenone and some of its p-substituted derivatives Synthesis of 2,2'-((1-phenylethane-1,1-diyl)bis(sulfanediyl))diacetic acid were obtained by us. A direct amidation reaction of Synthesis of 2,2'-((1-phenylethane-1,1-diyl)bis(sulfanediyl))diacetic acid with primary amines was conducted. The structure of the new compounds was interpreted by NMR spectra and X-ray structure analysis. As a result of studies, it was found that the greatest biological activity that can be useful in creating drugs is compound 1-(6-Methyl-3-phenyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl) ethanone. This compound is characterized by antioxidant effect significant effect on the functioning of biological membranes, and in low concentrations (below 7.5 mg/l) it stabilizes the membranes with an erythrocyte. The effect of an increase in the membrane potential of mitochondria was discovered, probably associated with the ability to bind to carrier proteins. In addition, when virtually predicting the spectrum of biological activity, a number of properties are shown that have promise when creating new drugs. (C) 2020 Published by Elsevier B.V.