Design and Synthesis of m1-Selective Muscarinic Agonists: (R)-(−)-(Z)-1-Azabicyclo[2.2.1]heptan-3-one, O-(3-(3‘-Methoxyphenyl)-2-propynyl)- oxime Maleate (CI-1017), a Functionally m1-Selective Muscarinic Agonist
Journal of Medicinal Chemistry1998Vol. 41(14), pp. 2524–2536
Citations Over Time
Haile Tecle, Stephen D. Barrett, David Lauffer, Corinne E. Augelli‐Szafran, Mark R. Brann, Michael J. Callahan, Bradley W. Caprathe, Robert E. Davis, Patricia D. Doyle, David C. Eubanks, William Lipiniski, Tara Mirzadegan, Walter H. Moos, D.W. Moreland, Carrie B. Nelson, Michael R. Pavia, C Raby, Roy D. Schwarz, Carolyn J. Spencer, Anthony J. Thomas, Juan C. Jaén
Abstract
The synthesis and SAR of a series of (Z)-(+/-)-1-azabicyclo[2.2. 1]heptan-3-one, O-(3-aryl-2-propynyl)oximes are described. The biochemistry and pharmacology of 24Z (PD 142505) and its enantiomers are highlighted. 24Z is functionally an m1-selective muscarinic agonist. Efficacy and m1 selectivity reside in the R enantiomer, (R)-24Z (CI-1017).
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