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3-(4-Piperidinyl)indoles and 3-(4-piperidinyl)pyrrolo-[2,3-b]pyridines as ligands for the ORL-1 receptor. 2006

Gilles C Bignan, and Kathleen Battista, and Peter J Connolly, and Michael J Orsini, and Jingchun Liu, and Steven A Middleton, and Allen B Reitz
Johnson & Johnson Pharmaceutical Research and Development, L.L.C PO Box 300, 1000 Route 202, Raritan, NJ 08869, USA. gbignan@gmail.com

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.

UI MeSH Term Description Entries
D007211 Indoles Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D008024 Ligands A molecule that binds to another molecule, used especially to refer to a small molecule that binds specifically to a larger molecule, e.g., an antigen binding to an antibody, a hormone or neurotransmitter binding to a receptor, or a substrate or allosteric effector binding to an enzyme. Ligands are also molecules that donate or accept a pair of electrons to form a coordinate covalent bond with the central metal atom of a coordination complex. (From Dorland, 27th ed) Ligand
D010880 Piperidines A family of hexahydropyridines.
D011725 Pyridines Compounds with a six membered aromatic ring containing NITROGEN. The saturated version is PIPERIDINES.
D011758 Pyrroles Azoles of one NITROGEN and two double bonds that have aromatic chemical properties. Pyrrole
D011957 Receptors, Opioid Cell membrane proteins that bind opioids and trigger intracellular changes which influence the behavior of cells. The endogenous ligands for opioid receptors in mammals include three families of peptides, the enkephalins, endorphins, and dynorphins. The receptor classes include mu, delta, and kappa receptors. Sigma receptors bind several psychoactive substances, including certain opioids, but their endogenous ligands are not known. Endorphin Receptors,Enkephalin Receptors,Narcotic Receptors,Opioid Receptors,Receptors, Endorphin,Receptors, Enkephalin,Receptors, Narcotic,Receptors, Opiate,Endorphin Receptor,Enkephalin Receptor,Normorphine Receptors,Opiate Receptor,Opiate Receptors,Opioid Receptor,Receptors, Normorphine,Receptors, beta-Endorphin,beta-Endorphin Receptor,Receptor, Endorphin,Receptor, Enkephalin,Receptor, Opiate,Receptor, Opioid,Receptor, beta-Endorphin,Receptors, beta Endorphin,beta Endorphin Receptor,beta-Endorphin Receptors
D000094942 Nociceptin Receptor A member of the opioid subfamily of the G PROTEIN-COUPLED RECEPTORS. It is the receptor for the endogenous neuropeptide nociceptin. It functions in modulating NOCICEPTION and the perception of pain. KOR-3 Protein,Kappa3-Related Opioid Receptor,MOR-C Protein,Nociceptin Receptors,OFQ Receptor,OFQ Receptors,ORL1 Receptor,ORL1 Receptors,Opiate Receptor-Like 1,Opioid Receptor-Like Protein,Opioid-Receptor-Like 1 Protein,Orphanin FQ Receptor,Orphanin FQ Receptors,Receptor, Nociceptin,Receptor, OFQ,Receptor, Orphanin FQ,Receptors, ORL1,Noci-R,1 Protein, Opioid-Receptor-Like,1, Opiate Receptor-Like,FQ Receptor, Orphanin,FQ Receptors, Orphanin,MOR C Protein,Noci R,Opioid Receptor Like 1 Protein,Protein, KOR-3,Protein, MOR-C,Protein, Opioid Receptor-Like,Protein, Opioid-Receptor-Like 1,Receptor, Kappa3-Related Opioid,Receptor-Like 1, Opiate,Receptor-Like Protein, Opioid,Receptors, Nociceptin,Receptors, Orphanin FQ
D001665 Binding Sites The parts of a macromolecule that directly participate in its specific combination with another molecule. Combining Site,Binding Site,Combining Sites,Site, Binding,Site, Combining,Sites, Binding,Sites, Combining
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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