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.
Article Details
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Tecle H, Barrett SD, Lauffer DJ, Augelli-Szafran 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
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.
J Med Chem. 1998 Jul 2;41(14):2524-36.
- PubMed ID
- 9651157 [ View in PubMed]
- 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).
DrugBank Data that Cites this Article
- Binding Properties
Drug Target Property Measurement pH Temperature (°C) Carbamoylcholine Muscarinic acetylcholine receptor M1 IC 50 (nM) 4090 N/A N/A Details Carbamoylcholine Muscarinic acetylcholine receptor M2 EC 50 (nM) 61000 N/A N/A Details Carbamoylcholine Muscarinic acetylcholine receptor M2 IC 50 (nM) 119000 N/A N/A Details Carbamoylcholine Muscarinic acetylcholine receptor M4 EC 50 (nM) 60000 N/A N/A Details