Atropisomeric Properties of the Dibenzo[b,d]azepin-6-one Nucleus
Authors:
- 9 October 2008
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (21) , 4871-4874
Abstract
Dibenzo[b,d]azepin-6-ones (2a,b) were separated by chiral HPLC into the aR- and aS-atropisomers with high stereochemical stability, and methylation at C7 of 2a stereoselectively gave the (aR*,7R*) isomer (4a), which converted to the thermodynamically stable (aS*,7R*) atropisomer (5a) after heating.Keywords
This publication has 13 references indexed in Scilit:
- Divergent Synthesis of Multifunctional Molecular Probes To Elucidate the Enzyme Specificity of Dipeptidic γ-Secretase InhibitorsACS Chemical Biology, 2007
- C-terminal Fragment of Presenilin Is the Molecular Target of a Dipeptidic γ-Secretase-specific Inhibitor DAPT (N-[N-(3,5-Difluorophenacetyl)-L-alanyl]-S-phenylglycine t-Butyl Ester)Journal of Biological Chemistry, 2006
- Diastereoselective Synthesis of Atropisomeric 3-(2-Substituted Aryl)quinazolin-4-ones and Their Stereochemical PropertiesHETEROCYCLES, 2006
- Quantitative Measurement of Changes in Amyloid-β(40) in the Rat Brain and Cerebrospinal Fluid following Treatment with the γ-Secretase Inhibitor LY-411575 [N2-[(2 S)-2-(3,5-Difluorophenyl)-2-hydroxyethanoyl]-N1-[(7 S)-5-methyl-6-oxo-6,7-dihydro-5 H-dibenzo[b,d]azepin-7-yl]-l-alaninamide]The Journal of Pharmacology and Experimental Therapeutics, 2005
- Lack of Specific Amyloid-β(1-42) Suppression by Nonsteroidal Anti-Inflammatory Drugs in Young, Plaque-Free Tg2576 Mice and in Guinea Pig Neuronal CulturesThe Journal of Pharmacology and Experimental Therapeutics, 2005
- Amide-based atropisomers in tachykinin NK1-receptor antagonists: synthesis and antagonistic activity of axially chiral N-benzylcarboxamide derivatives of 2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocin-6-oneTetrahedron, 2004
- Studies of Aβ Pharmacodynamics in the Brain, Cerebrospinal Fluid, and Plasma in Young (Plaque-Free) Tg2576 Mice Using the γ-Secretase Inhibitor N2-[(2 S)-2-(3,5-Difluorophenyl)-2-hydroxyethanoyl]-N1-[(7 S)-5-methyl-6-oxo-6,7-dihydro-5 H-dibenzo[b,d]azepin-7-yl]-L-alaninamide (LY-411575)The Journal of Pharmacology and Experimental Therapeutics, 2004
- Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger–aza-Wittig reaction of ω-azido pentafluorophenyl ester: synthesis and biological evaluation of LY411575 analoguesTetrahedron Letters, 2004
- Axially Chiral 1,7-Naphthyridine-6-carboxamide Derivatives as Orally Active Tachykinin NK1 Receptor Antagonists: Synthesis, Antagonistic Activity, and Effects on Bladder FunctionsJournal of Medicinal Chemistry, 1999
- Enantioselective synthesis of an axially chiral 1,7-naphthyridine-6-carboxamide derivative having potent antagonist activity at the NK1 receptorChemical Communications, 1998