28936-91-6Relevant academic research and scientific papers
Microwave-assisted synthesis of functionalized spirohydantoins as 3-D privileged fragments for scouting the chemical space
Prevet, Hugues,Flipo, Marion,Roussel, Pascal,Deprez, Benoit,Willand, Nicolas
supporting information, p. 2888 - 2894 (2016/06/14)
Fragment-based drug design has been successfully applied to a large set of proteins, however in order to expand this concept to the most demanding targets, such as protein-protein interactions, it is required to enrich current fragment libraries with new and original 3D privileged fragments. Our goal was to develop a rapid microwave-assisted synthesis of 27 new privileged spirohydantoin fragments. Among them 24 compounds showed a high water solubility. These molecules were plotted according to the normalized principal moments of inertia of their minimized conformers, and most of the compounds were prone to occupy under-populated regions of the triangular plot. Finally we demonstrated that the hydantoin ring can be selectively N-monoalkylated providing the access to rapid functionalization for further elaboration.
