What is it about?
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-(trifluoromethoxy)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-1H-indol-3-yl)ethyl]-4-{4-[4(trifluoromethoxy)phenoxy]piperidin-1-yl}benzamide (1b) and N-{4-[4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl]benzyl}-1H-indolyl-2-carboxamide (2b), are endowed with antitubercular properties, which merit further investigation.
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Perspectives
The design of these derivatives was based on the incorporation of long-tailed antitubercular pharmacophores into indole and adamantane scaffolds, respectively through an amide and reverse amide bond. The results of the antimycobacterial screening have shown marginal activity. These findings will direct our future design on related structures focusing on the length of the spacer between the nuclei and the side pharmacophores in order to achieve the ultimate antimycobacterial potential.
Ioannis P. Papanastasiou
National and Kapodistrian University of Athens
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This page is a summary of: Synthesis of New Indole and Adamantane Amido Derivatives with Pharmacological Interest, ChemistrySelect, August 2019, Wiley,
DOI: 10.1002/slct.201901303.
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