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. 1998 Jul 2;41(14):2524-36.
doi: 10.1021/jm960683m.

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

H Tecle  1 , S D Barrett, D J Lauffer, C Augelli-Szafran, M R Brann, M J Callahan, B W Caprathe, R E Davis, P D Doyle, D Eubanks, W Lipiniski, T Mirzadegan, W H Moos, D W Moreland, C B Nelson, M R Pavia, C Raby, R D Schwarz, C J Spencer, A J Thomas, J C Jaen
Affiliations

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

H Tecle et al. J Med Chem. .

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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