201660-24-4Relevant articles and documents
Synthesis of 2-phenyloxazole derivatives containing amino acids as insulin sensitivity enhancers for treatment of type II diabetes
Faul, Margaret M.,Winneroski, Leonard L.,York, Jeremy S.,Reinhard, Matt R.,Hoying, Richard C.,Gritton, William H.,Dominianni, Samuel J.
, p. 689 - 704 (2007/10/03)
The search for Insulin Sensitivity Enhancers (ISE) for use in the treatment of Non-Insulin Dependent Diabetes Mellitus (NIDDM) has led to the preparation of N-[(phenylmethoxy)carbonyl]-O-[[4-[2-(2-phenyl-4-oxazolyl)-ethoxy]phenyl] methyl]-L-serine (1) and 7-[2-(2-phenyl-4-oxazolyl)ethoxyl]-L-1,2,3,4-tetrahydro-N-Cbz- isoquinoline-3-carboxylic acid (2), that contain a 2-phenyloxazole moiety linked to an amino acid in place of the 2,4-thiazolidinedione pharmacophore. The 2-phenyloxazole was incorporated into 1 and 2 in high yield by alkylation of 4-hydroxybenzaldehyde or methyl 7-1,2,3,4-tetrahydro-N-benzyloxycarbonyl-hydroxyisoquinoline-3-carboxylate with 2-(2-phenyl-4-oxazolyl)ethyl p-toluenesulfonate (16). Successful incorporation of serine into 1 required use of an N-trityl protecting group to minimize β-elimination and epimerization at the α-center.