title: N-acylphenylalanines and related compounds. A new class of oral hypoglycemic agents.
abstract: N-Benzoyl-DL-phenylalanine (1) was found to possess hypoglycemic activity. A series of the analogues of compound 1 were prepared and evaluated for their blood glucose lowering activity. Both the steric effects of the phenylalanine moiety and the effects of variations in the acyl moiety were investigated. This study elucidated some of the structure-activity relationships and led to the development of N-(4-ethylbenzoyl)-D-phenylalanine (34), which was 50 times more potent than the initial compound 1.
authors.affiliation: Central Research Laboratories, Ajinomoto Co., Inc., Kawasaki, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Shinkai
authors.forename: K
authors.initials: K
authors.lastname: Toi
authors.forename: I
authors.initials: I
authors.lastname: Kumashiro
authors.forename: Y
authors.initials: Y
authors.lastname: Seto
authors.forename: M
authors.initials: M
authors.lastname: Fukuma
authors.forename: K
authors.initials: K
authors.lastname: Dan
authors.forename: S
authors.initials: S
authors.lastname: Toyoshima
mesh_terms: D000818:Animals; D007004:Hypoglycemic Agents / Q000138:chemical synthesis*; D051379:Mice; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013329:Structure-Activity Relationship
chemical_list: D007004:Hypoglycemic Agents; C057581:N-(4-ethylbenzoyl)phenylalanine; D010649:Phenylalanine