Bioorganic & Medicinal Chemistry Letters 2012-02-15

SAR of α7 nicotinic receptor agonists derived from tilorone: exploration of a novel nicotinic pharmacophore.

Michael R Schrimpf, Kevin B Sippy, Clark A Briggs, David J Anderson, Tao Li, Jianguo Ji, Jennifer M Frost, Carol S Surowy, William H Bunnelle, Murali Gopalakrishnan, Michael D Meyer

Index: Bioorg. Med. Chem. Lett. 22 , 1633-8, (2012)

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Abstract

The well-known interferon-inducer tilorone was found to possess potent affinity for the agonist site of the α7 neuronal nicotinic receptor (K(i)=56 nM). SAR investigations determined that both basic sidechains are essential for potent activity, however active monosubstituted derivatives can also be prepared if the flexible sidechains are replaced with conformationally rigidified cyclic amines. Analogs in which the fluorenone core is replaced with either dibenzothiophene-5,5-dioxide or xanthenone also retain potent activity.Copyright © 2012 Elsevier Ltd. All rights reserved.


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