The continuing effort to create molecular diversity for use in early stage small molecule drug discovery has led to many new synthetic strategies for the production of compound libraries. In relatively recent years greater emphasis has been placed on the provision of scaffold families, particularly highly saturated versions thereof, as an effective way of exploring “chemical space”, a concept which includes the effect of molecular architecture and properties on the micro-environment created by library molecules. The presence of multiple stereocenters on a central molecular platform offers opportunities for creating a wide range of such micro-environments and attracted our attention as being a desirable feature in compound library production. Multiple stereocenters afford diastereodiversity, and if the stereocenters are present in different relative orientations, regiodiversity is also obtained. Thus, scaffold families bearing stereocenters that can be positioned at will and that have multiple sites for chemical diversification are attractive vehicles for library production.<br/>Our interest is developing new methodology for the synthesis of a library of substituted piperazines scaffolds and further utilize them for FBLD purposes. Piperazines contain the elements that lend themselves to facile creation of molecular diversity; saturation, multiple sites of nitrogen diversification and four carbon positions at which diastereodivergence and regiodivergence can be created.

Synthesis of enantiomerically pure 6-substituted-piperazine-2-acetic acid esters for Fragment Based Lead Discovery (FBLD)

253rd National Meeting (2017)

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