Efficient Synthesis of Stereodivergent Triazole Linked 1,4-Naphthoquinone based Acyclic Polyols as Glycohybrids

Carbohydrates, once primarily recognized for their role as energy sources, their derivatives have recently attracted considerable interest in drug discovery because of their structural diversity and wide range of biological activities. Nonetheless, unmodified carbohydrates typically display weak bioactivity and less favourable chemical and physical properties. To overcome these limitations, researchers have integrated bioactive scaffolds into carbohydrate derived structures to enhance their biological potency and optimize their overall properties. We have designed a concise synthetic route that combines various 2-O/NH-propargyl 1,4-naphthoquinones with carbohydrate derived 5-azido glycols to prepare new molecular scaffold as glycohybrid. Hence, a straightforward and efficient copper-catalyzed method for synthesizing a stereodivergent triazole linked polyol-naphthoquinone conjugates and molecular docking studies with IRAK1 is disclosed herein. This approach successfully yielded new chiral polyol-naphthoquinone conjugates in excellent yields.