Novel bicyclic diketopiperazines as scaffolds for non-covalent self-assembly

ORGN 585

Yanming Du1, Christopher J. Creighton2, Brett A. Tounge2, and Allen B. Reitz3. (1) Johnson & Johnson Pharmaceutical Research and Development, Spring House, PA 19477, (2) Department of Drug Discovery, R. W. Johnson Pharmaceutical Research Institute, P. O. Box 0776, Welsh and McKean Roads, Spring House, PA 19477-0776, (3) Drug Discovery, R W Johnson Pharmaceutical Research Institute, Welsh and McKean Roads, Spring House, PA 19477-0776

The design and synthesis of 7,9-diazabicyclo[4.2.2]dec-3-ene-8,10-dione 1 and saturated derivative 2 will be described. These compounds form non-covalent networks as determined by X-ray crystal structure analysis, which have utility in understanding hydrophobic and hydrophilic interactions (c.f. Whitesides et al J. Am. Chem. Soc. 1997, 119, 11807). In the structures determined for 1 and 2, the carbon bridge of the bicyclic diketopiperazine plays a critical role in establishing the conformational preferences and non-covalent bonding patterns that are observed.

 

Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003