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

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发表日期：

2024年7月1日

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V. A. Ostrovskii,
N. T. Shmaneva,
I. S. Ershov,
D. V. Antonenko,
M. A. Skryl’nikova,
A. V. Khramchikhin,
E. N. Chernova,
A. Yu. Grishina,
N. A. Anisimova,
S. M. Napalkova,
O. V. Buyuklinskaya,
V. S. Mazhai,
Yu. N. Pavlyukova,
R. E. Trifonov

摘要

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.