The synthesis and physicochemical properties of 2-(5-methoxyphenyl-1H-1,2,4-triazole-3-ylthio) acetonitriles and their iminoethers

Yu. G. Sameluk, A. G. Kaplaushenko

Abstract


With the purpose of further search of biologically active substances among 5-(2-, 3-, 4-methoxyphenyl, 3,4,5- trimethoxyphenyl)-3-thio-1,2,4-triazoles and their derivatives 10 new compounds have been obtained. Acetonitrilothio- 1,2,4-triazoles have been synthesized by alkylation of 5-(2-, 3-, 4-methoxyphenyl and 3,4,5-trimethoxyphenyl)- 3-thio-1,2,4-triazoles with halogenonitriles; the primary computer pharmacological screening has shown that the class of compounds mentioned can show such types of the pharmacological activity as antitumor, antiinflammatory and antioxidant ones. Alkylation of 5-R-1,2,4-triazole-3-thiols has been carried out in the medium of anhydrous alcohol or aprotic solvents. It has been found that replacement of the alcoholic solvent by the aprotic one increases the quantitative yield of 5-R-1,2,4-triazol-3-thioacetonitrile; in aprotic solvents the presence of impurities of alkaline hydrolysis products is not practically observed. Iminoethers of 2-(5-(2-, 3-, 4-methoxyphenyl and 3,4,5-trimethoxyphenyl)-1H-1,2,4-triazole-3-ylthio)acetatic acids have been synthesized by saturation of 2-(5-(2-, 3-, 4-methoxyphenyl and 3,4,5-trimethoxyphenyl)-1H-1,2,4-triazol-3-ylthio)acetonitriles with the flow of dry in the alcoholic medium when constant cooling the reaction mixture to –5ºC. It has been found by the method of HPLC/DAD-MS that the qualitative yield of the target product depends on the maintenance of the temperature mode of the reaction mixture. The structure and individuality of the molecules of the substances synthesized have been proven by the method of 1H NMR-spectroscopy and HPLC/DAD-MS.


Keywords


1,2,4-triazoles; nitriles; iminoethers

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References


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DOI: https://doi.org/10.24959/ophcj.15.841

Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)