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Pyrrolidine and piperidine based chiral spiro and fused scaffolds via build/couple/pair approach
Mamidala R., Babu Damerla V.S., Gundla R., Chary M.T., Murthy Y.L.N.,
Published in
Volume: 4
Issue: 21
Pages: 10619 - 10626
A versatile stereoselective diversity oriented synthetic pathway to the possible spiro and fused diverse heterocyclic small molecules is described. The strategy involved the "build-couple-pair" approach involving an S NAr, Michael addition and Mannich reaction on chiral acyl bicyclic lactams 2a/b, followed by a cyclization onto the inbuilt scaffold electrophile, thereby leading to asymmetric fused and spirocyclic nitrogen heterocycles. A "post-pair" phase has been incorporated to generate more polar compounds. We used Principal Component Analysis (PCA) and polar moment of inertia to evaluate the shape-space diversity of our scaffolds with respect to a commercial database and observed extraordinary diversity within the scaffold network. We further calculated the polar surface area (PSA) of our molecules which is an indicator for drug cell permeability. © 2014 The Royal Society of Chemistry.
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