ORGN 680 |
| Kristofer K. Moffett, Dan Nguyen, Gary Flynn, Bruce D. Dorsey, and Enrique L. Michelotti. Chemistry, Locus Pharmaceuticals, Inc, 512 Townshipline Rd, Four Valley Square, blue bell, PA 19422 |
| A privileged structure is defined as a core template that is able to present high-affinity interactions to multiple receptor types. As part of our de novo designs of biologically active molecules utilizing Locus Core Technology we became interested in the spiro-piperidine-indoline core previously reported as a template for ligands to G-Protein Coupled Receptors. The designed targets include the core oxindole substituted with various substituents on the aromatic ring and aryl and heteroaryl substituted moieties on the piperidine ring nitrogen. Reported syntheses for this template were not satisfactory in efficiently providing the target molecules. In this presentation we wish to report a novel, high-yielding synthesis of the spiro-piperidine-indoline core from commercially available oxindoles based on an ozonolysis/reductive amination cyclization procedure.
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |