title: N-Benzoyl amino acids as LFA-1/ICAM inhibitors 1: amino acid structure-activity relationship.
abstract: The association of ICAM-1 with LFA-1 plays a critical role in several autoimmune diseases. N-2-Bromobenzoyl L-tryptophan, compound 1, was identified as an inhibitor to the formation of the LFA-1/ICAM complex. The SAR of the amino acid indicates that the carboxylic acid is required for inhibition and that L-histidine is the most favored amino acid.
authors.affiliation: Department of Bioorganic Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA 94080, USA. burdick.dan@gene.com
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Burdick
authors.forename: Ken
authors.initials: K
authors.lastname: Paris
authors.forename: Kenneth
authors.initials: K
authors.lastname: Weese
authors.forename: Mark
authors.initials: M
authors.lastname: Stanley
authors.forename: Maureen
authors.initials: M
authors.lastname: Beresini
authors.forename: Kevin
authors.initials: K
authors.lastname: Clark
authors.forename: Robert S
authors.initials: RS
authors.lastname: McDowell
authors.forename: James C
authors.initials: JC
authors.lastname: Marsters
authors.forename: Thomas R
authors.initials: TR
authors.lastname: Gadek
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002264:Carboxylic Acids / Q000737:chemistry / Q000494:pharmacology; D004797:Enzyme-Linked Immunosorbent Assay; D006639:Histidine / Q000737:chemistry / Q000494:pharmacology; D007202:Indicators and Reagents; D018799:Intercellular Adhesion Molecule-1 / Q000187:drug effects*; D016169:Lymphocyte Function-Associated Antigen-1 / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D000596:Amino Acids; D002264:Carboxylic Acids; D007202:Indicators and Reagents; D016169:Lymphocyte Function-Associated Antigen-1; D018799:Intercellular Adhesion Molecule-1; D006639:Histidine