Scalable ultrasound-assisted synthesis of hydroxy imidazole N-oxides and evaluation of their anti-proliferative activities; mechanistic insights into the deoximation of dioximes

Abstract

The development of synthetic methodologies that promote greener reactions have become so essential that it has slowly shaped the way chemists think about the construction of physiologically and chemically active compounds. The acid-catalyzed iminoketone - aldehyde condensations leading to Hydroxy imidazole N-oxides serve as robust strategies for forming C-N bonds. Considering all the existing challenges that come with the use of solvent and energy-intensive methodologies, herein a green synthetic strategy using ultrasound with optimization of reaction conditions and thorough investigation into the mechanism for obtaining the best yields are reported. Additionally, the importance of the Hydroxy Imidazole N-oxides synthesis is highlighted by their in vitro antiproliferative activity study. Though only satisfactory, the results are promising. It gives us scope for building upon this simple scaffold with appropriate functionalization, which may lead to furhter enhancement in their anti-proliferative activity.