353525-11-8

Basic information

• Product Name: methyl (4-amino-3-hydroxyphenyl)acetate
• Synonyms: methyl (4-amino-3-hydroxyphenyl)acetate
• CAS NO: 353525-11-8
• Molecular Weight: 181.191
• Mol File: 353525-11-8.mol

Chemical Properties

• Melting Point: 112-114 °C
• Boiling Point: 317.0±32.0 °C(Predicted)
• Density: 1.267±0.06 g/cm3(Predicted)
• CAS DataBase Reference: methyl (4-amino-3-hydroxyphenyl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (4-amino-3-hydroxyphenyl)acetate(353525-11-8)
• EPA Substance Registry System: methyl (4-amino-3-hydroxyphenyl)acetate(353525-11-8)

Safety Data

• Hazardous Substances Data: 353525-11-8(Hazardous Substances Data)

Upstream product

• 256453-84-6 2-(3-hydroxy-4-nitrophenyl)acetic acid methyl ester 

Downstream Products

• 1198054-21-5 methyl [2-(2-methylbenzyl)-6-benzoxazolyl]acetate 
• 1361414-56-3 trans-4-[1-[[2-(1-methyl-3-indolyl)-6-benzoxazolyl]acetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid 
• 1361414-57-4 methyl trans-4-[1-[[2-(1-methyl-3-indolyl)-6-benzoxazolyl]acetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate 
• 1361330-52-0 trans-4-[1-[(2-phenyl-6-benzoxazolyl)acetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid 
• 62143-69-5 2-phenyl-6-benzoxazolylacetic 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.

PHARMACEUTICALLY ACTIVE BENZOXAZOLE, BENZTHIAZOLE AND BENZIMIDAZOLE ACID DERIVATIVES

Compounds of formula (I): wherein R1, R2 and R3 are independently, hydrogen, halogen, CF3, OR6, NR7R8, NR8COR10, NR8SO2R10 or C1-6 alkyl optionally substituted by hydroxy, C1-6 alkoxy or NR7R8; R4 is NR8CONR8R9, NR8COR9, NR8SO2R9, or W-CONR8R9, where W is a bond, C1-6 alkylene, C2-6 alkenylene or C2-6 alkynylene; and R5 is Formula (A) methods for their synthesis, pharmaceutical compositions comprising them and their use in medicine, in particular for the treatment of cancer.