Synthesis and SAR studies of 1,4-diazabicyclo[3.2.2]nonane phenyl carbamates ― subtype selective, high affinity α7 nicotinic acetylcholine receptor agonists

Christopher J O'DONNELL; LANGU PENG; Brian T O'NEILL; Eric P ARNOLD; Robert J MATHER; Steven B SANDS; Alka SHRIKHANDE; Lorraine A LEBEL; Douglas K SPRACKLIN; Frank M NEDZA

doi:10.1016/j.bmcl.2009.06.059

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Synthesis and SAR studies of 1,4-diazabicyclo[3.2.2]nonane phenyl carbamates ― subtype selective, high affinity α7 nicotinic acetylcholine receptor agonists

Journal article

Peer reviewed

Synthesis and SAR studies of 1,4-diazabicyclo[3.2.2]nonane phenyl carbamates ― subtype selective, high affinity α7 nicotinic acetylcholine receptor agonists

Christopher J O'DONNELL, LANGU PENG, Brian T O'NEILL, Eric P ARNOLD, Robert J MATHER, Steven B SANDS, Alka SHRIKHANDE, Lorraine A LEBEL, Douglas K SPRACKLIN and Frank M NEDZA

Bioorganic & medicinal chemistry letters, Vol.19(16), pp.4747-4751

2009

DOI: 10.1016/j.bmcl.2009.06.059

PMID: 19576766

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https://doi.org/10.7270/q21g0n69View

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Abstract

The synthesis and SAR studies about the bicyclic amine, carbamate linker and aromatic ring of a 1,4-diazabicyclo[3.2.2]nonane phenyl carbamate series of alpha7 nAChR agonists is described. The development of the medicinal chemistry strategy and SAR which led to the identification of 5 and 7aa as subtype selective, high affinity alpha7 agonists as excellent leads for further evaluation is discussed, along with key physicochemical and pharmacokinetic data highlighting their lead potential.

Psychopharmacology

Neuropharmacology

Psycholeptics: tranquillizer, neuroleptic

Psychology. Psychoanalysis. Psychiatry

Neurotransmitters. Neurotransmission. Receptors

Pharmacology. Drug treatments

Biological and medical sciences

Cholinergic system

Medical sciences

Details

Title: Subtitle: Synthesis and SAR studies of 1,4-diazabicyclo[3.2.2]nonane phenyl carbamates ― subtype selective, high affinity α7 nicotinic acetylcholine receptor agonists
Creators: Christopher J O'DONNELL - Neuroscience Medicinal Chemistry, Pfizer Global Research & Development, Eastern Point Road, Groton, CT 06340, United States
LANGU PENG - Neuroscience Medicinal Chemistry, Pfizer Global Research & Development, Eastern Point Road, Groton, CT 06340, United States
Brian T O'NEILL - Neuroscience Medicinal Chemistry, Pfizer Global Research & Development, Eastern Point Road, Groton, CT 06340, United States
Eric P ARNOLD - Neuroscience Medicinal Chemistry, Pfizer Global Research & Development, Eastern Point Road, Groton, CT 06340, United States
Robert J MATHER - Neuroscience Medicinal Chemistry, Pfizer Global Research & Development, Eastern Point Road, Groton, CT 06340, United States
Steven B SANDS - Neuroscience Medicinal Chemistry, Pfizer Global Research & Development, Eastern Point Road, Groton, CT 06340, United States
Alka SHRIKHANDE - Neuroscience Medicinal Chemistry, Pfizer Global Research & Development, Eastern Point Road, Groton, CT 06340, United States
Lorraine A LEBEL - Neuroscience Medicinal Chemistry, Pfizer Global Research & Development, Eastern Point Road, Groton, CT 06340, United States
Douglas K SPRACKLIN - Neuroscience Medicinal Chemistry, Pfizer Global Research & Development, Eastern Point Road, Groton, CT 06340, United States
Frank M NEDZA - Neuroscience Medicinal Chemistry, Pfizer Global Research & Development, Eastern Point Road, Groton, CT 06340, United States
Resource Type: Journal article
Publication Details: Bioorganic & medicinal chemistry letters, Vol.19(16), pp.4747-4751
DOI: 10.1016/j.bmcl.2009.06.059
PMID: 19576766
NLM abbreviation: Bioorg Med Chem Lett
ISSN: 0960-894X
eISSN: 1464-3405
Publisher: Elsevier
Language: English
Date published: 2009
Academic Unit: Endocrinology and Metabolism; Internal Medicine
Record Identifier: 9984094366902771

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