Issue 7, 2014
From the journal:

MedChemComm

Synthesis, enantiomeric separation and docking studies of spiropiperidine analogues as ligands of the nociceptin/orphanin FQ receptor†

Umberto M. Battisti,a   Sandra Corrado,a   Claudia Sorbi,a   Andrea Cornia,b   Annalisa Tait,a   Davide Malfacini,c   Maria Camilla Cerlesi,c   Girolamo Calòc  and  Livio Brasili*a  

* Corresponding authors

a Department of Life Sciences, University of Modena & Reggio Emilia, Via G. Campi 183, 41125 Modena, Italy
E-mail: livio.brasili@unimore.it
Fax: +39 0592055131
Tel: +39 0592055139

b Department of Chemical and Geological Sciences, University of Modena & Reggio Emilia, Via G. Campi 183, 41125 Modena, Italy

c Department of Medical Sciences, Section of Pharmacology and National Institute of Neuroscience, University of Ferrara, Via Fossato di Mortara, 64/B, 44121 Ferrara, Italy

Abstract

A series of triazospirodecanone derivatives were synthesized as potential NOP ligands. 8-(Chroman-4-yl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (4) and its 5-fluoro analogue (18) proved to be active as agonists with EC50 values in the submicromolar range. Single enantiomers of compound 4 were separated and tested as NOP agonists; the eutomer R-(+)-4 showed a pEC50 of 7.34. Finally docking studies were performed on the NOP receptor to identify the most significant stereospecific interactions.

Graphical abstract: Synthesis, enantiomeric separation and docking studies of spiropiperidine analogues as ligands of the nociceptin/orphanin FQ receptor

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Article information

DOI
https://doi.org/10.1039/C4MD00082J
Article type
Concise Article
Submitted
24 Feb 2014
Accepted
22 Apr 2014
First published
23 Apr 2014

Med. Chem. Commun., 2014,5, 973-983

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Synthesis, enantiomeric separation and docking studies of spiropiperidine analogues as ligands of the nociceptin/orphanin FQ receptor

U. M. Battisti, S. Corrado, C. Sorbi, A. Cornia, A. Tait, D. Malfacini, M. C. Cerlesi, G. Calò and L. Brasili, Med. Chem. Commun., 2014, 5, 973 DOI: 10.1039/C4MD00082J

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