Synthesis of New Indole and Adamantane Amido Derivatives with Pharmacological Interest

Abstract The synthesis and preliminary pharmacological evaluation of new indole and adamantane amido derivatives is described. The design was based on the pharmacophoric properties of 4‐{4‐[4‐(trifluoromethoxy)phenoxy]piperidin‐1‐yl), 6‐[4‐(trifluoro methoxy)phenyl]pyridin‐3‐yl and 4‐(trifluoro)phenyl tails, which are present as side chains in the structures of promising drug candidates, currently in clinical tests. These pharmacophores were incorporated into the indole and adamantane scaffolds, respectively. The new derivatives were evaluated for their antimycobacterial potential. The following amides, N ‐[2‐(5‐methoxy‐1 H ‐indol‐3‐yl)ethyl]‐4‐{4‐[4(trifluoromethoxy)phenoxy]piperidin‐1‐yl}benzamide ( 1 b ) and N ‐{4‐[4‐(4‐(trifluoromethoxy)phenoxy)piperidin‐1‐yl]benzyl}‐1 H ‐indolyl‐2‐carboxamide ( 2 b ), are endowed with antitubercular properties, which merit further investigation.