DOI: https://doi.org/10.24959/ophcj.13.772

The search for new biologically active substances among derivatives of 3-mercapto-4-amino- 5-cyclohexyl-1,2,4-triazole(4h)

N. B. Saidov, V. A. Georgiyants, N. V. Garna

Abstract


Synthesis of the series of new 4-phenyl-5-cyclohexyl-1,2,4-triazole(4H)-3-yl thioacetanilides is described. The key intermediate – 4-phenyl-5-cyclohexyl-3-mercapto-1,2,4-triazole(4H) has been synthesized started from cyclohexane carboxylic acid through its methyl ester, then hydrazide and the corresponding potassium 3-cyclohexyl dithiocarbazate after cyclisation with hydrazine hydrate. The end products 6a-u have been obtained by alkylation of the key intermediate 5 with chloroacetic acid anilides in the presence of basic catalysts. The purity of the compounds synthesized has been monitored by TLC. The structure of compounds synthesized has been proven by elemental analysis data and NMR spectra. In NMR-spectra the result of alkylation has been proven by disappearence of the chemical shift of the mercaptogroup. All compounds – both intermediate 5 and end products 6a-u contain signals of the cyclohexane system protons as two multiplets near 2.80 ppm (CH) and at 1.92-1.11 ppm (CH2)5; 4-aminogroup protons as a singlet signal at 5.92-5.87 ppm. The preliminary prediction of the possible pharmacological activity by computer prognosis (PASS programme) has been carried out. Among activities, which are the most probable for some of the substances synthesized, are ligase inhibitor, interferon agonist, antihypertensive, thyroid hormone antagonist, sedative, antiviral (Pa = 0.554-0.729). Due to prognosis and analysis of logical data the substances synthesized will be examined as possible antiviral agents.


Keywords


3-mercapto-1,2,4-triazole; derivatives; alkylation; synthesis; pharmacological activity prognosis

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