441769-12-6

Basic information

• Product Name: C₂₉H₃₄FN₃O₅
• CAS NO: 441769-12-6
• Molecular Weight: 523.604
• Mol File: 441769-12-6.mol

Chemical Properties

• CAS DataBase Reference: C₂₉H₃₄FN₃O₅(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₉H₃₄FN₃O₅(441769-12-6)
• EPA Substance Registry System: C₂₉H₃₄FN₃O₅(441769-12-6)

Safety Data

• Hazardous Substances Data: 441769-12-6(Hazardous Substances Data)

Upstream product

• 256453-94-8 2-(2-methylphenylamino)-6-benzoxazolylacetic acid 
• 441769-11-5 methyl trans-4-[(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate 
• 441769-11-5 methyl cis-4-[(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate 
• 441769-11-5 methyl 4-[(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate 

Downstream Products

• 441768-99-6 cis-4-[1-[2-(2-methylphenylamino)-6-benzoxazolylacetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid 
• 441768-99-6 trans-4-[1-[2-(2-methylphenylamino)-6-benzoxazolylacetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid 

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.