Application of the bridgehead fragments for the design of conformationally restricted melatonin analogues

Conformationally constrained analogues of the hormone melatonin with a side chain incorporated into the bicyclic bridgehead core were synthesized based on the homology modeling and molecular docking studies performed for the MT2 melatonin receptor. The methoxy-indole derivative fused with exo-N-acetamino-substituted bicyclo[2.2.2]octane was found to possess nanomolar MT2 receptor affinity. (C) 2011 Elsevier Inc. All rights reserved.