3-(4-Piperidinyl)indoles and 3-(4-piperidinyl)pyrrolo-[2,3-b]pyridines as ligands for the ORL-1 receptor

Gilles C Bignan; Kathleen Battista; Peter J Connolly; Michael J Orsini; Jingchun Liu; Steven A Middleton; Allen B Reitz

doi:10.1016/j.bmcl.2006.03.094

3-(4-Piperidinyl)indoles and 3-(4-piperidinyl)pyrrolo-[2,3-b]pyridines as ligands for the ORL-1 receptor

Bioorg Med Chem Lett. 2006 Jul 1;16(13):3524-8. doi: 10.1016/j.bmcl.2006.03.094. Epub 2006 Apr 24.

Authors

Gilles C Bignan¹, Kathleen Battista, Peter J Connolly, Michael J Orsini, Jingchun Liu, Steven A Middleton, Allen B Reitz

Affiliation

¹ Johnson & Johnson Pharmaceutical Research and Development, L.L.C PO Box 300, 1000 Route 202, Raritan, NJ 08869, USA. [email protected]

PMID: 16632355
DOI: 10.1016/j.bmcl.2006.03.094

Abstract

A novel series of indoles and 1H-pyrrolo[2,3-b]pyridines having a piperidine ring at the 3-position were synthesized and found to bind with high affinity to the ORL-1 receptor. Structure-activity relationships at the piperidine nitrogen were investigated in each series. Substitution on the phenyl ring and nitrogen atom of the indole and 1H-pyrrolo[2,3-b]pyridine cores generated several selective high-affinity ligands that were agonists of the ORL-1 receptor.

MeSH terms

Binding Sites
Indoles / chemical synthesis
Indoles / chemistry
Indoles / pharmacology*
Ligands
Molecular Structure
Nociceptin Receptor
Piperidines / chemical synthesis
Piperidines / chemistry
Piperidines / pharmacology*
Pyridines / chemistry
Pyridines / pharmacology*
Pyrroles / chemical synthesis
Pyrroles / chemistry
Pyrroles / pharmacology*
Receptors, Opioid / agonists*
Structure-Activity Relationship

Substances

Indoles
Ligands
Piperidines
Pyridines
Pyrroles
Receptors, Opioid
Nociceptin Receptor