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

Authors
TECLE H BARRETT SD LAUFFER DJ AUGELLISZAFRAN C BRANN MR CALLAHAN MJ CAPRATHE BW DAVIS RE DOYLE PD EUBANKS D LIPINISKI W MIRZADEGAN T MOOS WH MORELAND DW NELSON CB PAVIA MR RABY C SCHWARZ RD SPENCER CJ THOMAS AJ JAEN JC
Citation
H. Tecle et al., 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 chemistry, 41(14), 1998, pp. 2524-2536
Citations number
56
Categorie Soggetti
Chemistry Medicinal
Journal title
Journal of medicinal chemistry → ACNP
ISSN journal
00222623
Volume
41
Issue
14
Year of publication
1998
Pages
2524 - 2536
Database
ISI
SICI code
0022-2623(1998)41:14<2524:DASOMM>2.0.ZU;2-S
Abstract
The synthesis and SAR of a series of (Z)-(+/-)-1-azabicyclo[2.2. 1]hep tan-3-one, O-(3-aryl-2-propynyl)oximes are described. The biochemistry and pharmacology of 24Z (PD 142505) and its enantiomers are highlight ed. 24Z is functionally an mi-selective muscarinic agonist. Efficacy a nd mi selectivity reside in the R enantiomer, (R)-24Z (CI-1017).