New 1,1-dibenzyl-3-(1-benzyl-1H-pyrazol-4-yl)-2-methylisothioureas: synthesis and evaluation of antioxidant activity

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发表日期：

2024年5月1日

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A. N. Proshin,
T. P. Trofimova,
A. A. Globa,
E. S. Dubrovskaya,
O. N. Zefirova,
N. A. Zefirov,
V. A. Tafeenko,
T. Ya. Dutova,
B. I. Ugrak,
I. V. Serkov

摘要

1,1-Dibenzyl-3-(1-benzyl-1 1H-pyrazol-4-yl)-2-methylisothioureas containing structural elements both of known antioxidants and glutamate receptor modulators were proposed as compounds with a dual mode of biological action, namely the antioxidant activity and the ability to influence the glutamatergic signaling system. The target compounds were synthesized by the reaction of substituted 4-amino-1-benzylpyrazoles with thiophosgene followed by the condensation of the resulting 1-benzyl-4-isothiocyanato-1H-pyrazoles with dibenzylamine and the subsequent S-methylation of the resulting thioureas. 1,1-Dibenzyl-3-[1-(3,4-dichlorobenzyl)- and 1,1-dibenzyl-3-[1-(2,4-dichlorobenzyl)-1H-pyrazol-4-yl]-2-methylisothioureas were found to have a moderate ability to protect neuroblastoma cells against the toxic effect of hydrogen peroxide, making these compounds interesting for further study of the modulatory activity toward glutamate receptors.