Arylaminoethyl succinamides as a novel series of noncovalent Cathepsin S inhibitors

MEDI 214

Arnab K. Chatterjee, akc@gnf.org1, Hong Liu, hliu@gnf.org1, David C Tully, dtully@gnf.org1, Jianhua Guo1, Robert Epple1, Ross Russo1, Jennifer A Williams, jwilliams@gnf.org1, Glen Spraggon2, Badry D. Bursulaya3, Thomas Hollenbeck4, Perry Gordon4, Tove Tuntland4, Jonathan Chang4, Jun Li5, and Jennifer L. Harris, harris@gnf.org5. (1) Department of Medicinal Chemistry, Genomics Institute of the Novartis Research Foundation, 10675 John J. Hopkins Drive, San Diego, CA 92121, (2) Department of Structural Biology, Genomics Institute of the Novartis Research Foundation, 10675 John J. Hopkins Drive, San Diego, CA 92121, (3) Department of Computational Chemistry, Genomics Institute of the Novartis Research Foundation, 10675 John J. Hopkins Drive, San Diego, CA 92121, (4) Department of Pharmacology, Genomics Institute of the Novartis Research Foundation, 10675 John J. Hopkins Drive, San Diego, CA 92121, (5) Department of Protease Biology, Genomics Institute of the Novartis Research Foundation, 10675 John J. Hopkins Drive, San Diego, CA 92121
Cathepsin S (CatS) is a lysosomal cysteine protease which has been shown to be critical in antigen presentation by the major histocompatibility class II complex (MHC II). Selective inhibition of CatS has been suggested as a potential therapeutic approach for the regulation of immune hyperresponsiveness, such as rheumatoid arthritis, multiple sclerosis, asthma and allergy. At GNF, we discovered a series of arylaminoethyl amides as noncovalent inhibitors of cathepsin S by HTS. Pharmacokinetic liabilities that often hinder the development of compounds against protease targets were addressed by the use of amino acid mimetics, such as succinic acids. Several novel noncovalent cathepsin S inhibitors were identified to possess high cathepsin S affinity (Ki < 10 nM) and excellent selectivity (>100 fold) over cathespins K, L and B. Molecular modeling, structure based drug design, synthesis and in vitro activity will be described.
 

General Poster Session
7:00 PM-9:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Medicinal Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006