441712-09-0

Basic information

• Product Name: 4-[(4S)-fluoro-1-[2-(2-methylphenylamino)-6-benzoxazolylacetyl]-(2S)-pyrrolidinylcarbonyl]-1-piperazinylacetic acid
• CAS NO: 441712-09-0
• Molecular Weight: 523.564
• Mol File: 441712-09-0.mol

Chemical Properties

• CAS DataBase Reference: 4-[(4S)-fluoro-1-[2-(2-methylphenylamino)-6-benzoxazolylacetyl]-(2S)-pyrrolidinylcarbonyl]-1-piperazinylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(4S)-fluoro-1-[2-(2-methylphenylamino)-6-benzoxazolylacetyl]-(2S)-pyrrolidinylcarbonyl]-1-piperazinylacetic acid(441712-09-0)
• EPA Substance Registry System: 4-[(4S)-fluoro-1-[2-(2-methylphenylamino)-6-benzoxazolylacetyl]-(2S)-pyrrolidinylcarbonyl]-1-piperazinylacetic acid(441712-09-0)

Safety Data

• Hazardous Substances Data: 441712-09-0(Hazardous Substances Data)

Upstream product

• 441714-16-5 C₂₉H₃₄FN₅O₅ 

Relevant articles and documents

A novel and potent VLA-4 antagonist based on trans-4-substituted cyclohexanecarboxylic acid

During the course of our study, it was revealed that the poor pharmacokinetic properties of a series of benzoic acid derivatives such as 1 should be attributed to the diphenylurea moiety. Thus, we replaced the diphenylurea moiety in 1 with a 2-(2-methylphenylamino)benzoxazole moiety which mimics the diphenylurea structure. However, this modification resulted in a significant decrease (3, IC50 = 19 nM) in VLA-4 inhibitory activity compared to 1 (IC50 = 1.6 nM). To address this discrepancy, we worked on optimization of the carboxylic acid moiety in compound 3. As a result, our efforts have led to the discovery of trans-4-substituted cyclohexanecarboxylic acid derivative 11b (IC50 = 2.8 nM) as a novel and potent VLA-4 antagonist. In addition, compound 11b exhibited favorable pharmacokinetic properties (CL = 3.3 ml/min/kg, F = 51%) in rats.