1,3,5-Triazepan-2,6-diones as Conformationally Constrained Dipeptide Mimetics. In Silico Guided Identification of sPLA2 Inhibitors

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The design and synthesis by combinatorial chemistry techniques of cyclic/polycyclic molecular frameworks that can efficiently distribute selected pharmacophores in the 3D space is an important method to identify small-molecules capable of modulating biological processes. In this context, heterocyclic systems derived from peptides (e.g. DKP, A) are of particular interest owing to the facile access, the chemical and stereochemical diversity of peptide derivatives, as well as enhanced diversity resulting from post-cyclization appending operations.

We recently developped the 1,3,5-triazepan-2,6-dione system B as a novel, conformationally restricted, and readily accessible class of dipeptidomimetics [13]. The synthesis of this densely functionalized 1,3,5-triazepan-2,6-dione skeleton is achieved in only 4 steps from a variety of simple linear dipeptide precursors. Molecular and structural diversity can be increased further through post-cyclization appending operations at urea n ...