Double-sided α-helix mimetics

The design and synthesis of substituted bis- and tris-benzamides is reported in which the projection of side-chain residues on both sides of an alpha-helix is reproduced. The scaffold is conformationally constrained by a series of intramolecular hydrogen bonds, allowing for spatial and angular mimicry of the i, i+2, i+4 and i+6 side-chains in the case of the bis-benzamide, and may be extended to higher-order oligomers. (C) 2011 Elsevier Ltd. All rights reserved.