2-(5-Phenyl-2H-tetrazol-2-yl)acetyl chloride as a key reagent in the synthesis of non-annulated polynuclear tetrazole-containing compounds with potential antidiabetic activity

Abstract

Non-annulated tetrazole-containing polynuclear compounds, in which heterocyclic fragments are bound by an acetamide linker were synthesized. The synthesis was accomplished by acylation of 2-hydrazinyl-4,6-dimethylpyrimidine, 4-amino-4H-1,2,4-triazol-3-thiol, 2-[(1-amino-1H-tetrazol-5-yl)thio]-N-tert-butylacetamide, 1-methyl-1H-tetrazol-5-amine, and 2-methyl-2H-tetrazol-5-amine with one key reagent, (5-phenyltetrazol-2-yl)acetyl chloride. Preliminary in silico studies showed the presence of the in vivo antidiabetic (diabetes 2 type) activity in N′-(4,6-dimethylpyrimidin-2-yl)-2-(5-phenyl-2H-tetrazol-2-yl)acetohydrazide. N-(3-Mercapto-4H-1,2,4-triazol-4-yl)-2-(5-phenyl-2H-tetrazol-2-yl)acetamide demonstrated minimal hypoglycemic activity in in vivo studies, at the same time, it showed pronounced activity as a drug for combating obesity.