Novel synthesis of the first new class of triazine sulfonamide thioglycosides and the evaluation of their anti-tumor and anti-viral activities against human coronavirus

Abstract

Novel class of triazine sulfonamide thioglycosides was designed and synthesized. Those novel structures comprising three essential and pharmacological significant moieties such as the triazine, sulfonamide, and thioglycosidic scaffolds. The triazine sulfonamides were furnished <i>via</i> a direct approach starting from potassium cyanocarbonimidodithioate, then the corresponding triazine sulfonamide thioglycosides were generated using the peracylated <i>α</i>-d-<i>gluco</i>- and galacto-pyranosyl bromides. Anti-viral evaluation of compounds <i>in vitro</i> against HCoV-229E virus revealed that some compounds possess promising activity. Compounds <b>4a</b>, <b>4b</b>, <b>4d</b>, <b>6d</b> and <b>6e</b> indicate from moderate to low antiviral activity against low pathogenic coronavirus 229E in comparison with remdesivir at a concentration of 100 µg/mL. Additionally their <i>in vitro</i> anti-proliferative effects against NCI 60 cancer cell lines cell lines were also investigated. Compound <b>4a</b>, the most potent compound among the estimated compounds, revealed remarkably lowest cell growth promotion against CNS cancer SNB-75, and renal cancer UO-31.