343305-24-8

Basic information

• Product Name: methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate
• Synonyms: methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate
• CAS NO: 343305-24-8
• Molecular Weight: 476.483
• Mol File: 343305-24-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate(343305-24-8)
• EPA Substance Registry System: methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate(343305-24-8)

Safety Data

• Hazardous Substances Data: 343305-24-8(Hazardous Substances Data)

Upstream product

• 343305-18-0 3-pivaloyloxy-5-(4-methoxyphenyl)-4-methyl-isoxazole 
• 343305-15-7 5-(4-methoxyphenyl)-4-methyl-3-isoxazolol 
• 86109-34-4 methyl 3-(4'-methoxyphenyl)-2-methyl-3-oxopropanoate 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 121-98-2 methyl 4-methoxybenzoate 
• 60187-67-9 dimethyl acetamidomalonate 
• 343305-21-5 4-bromomethyl-3-pivaloyloxy-5-(4-methoxyphenyl)isoxazole 

Relevant articles and documents

Structural determinants for AMPA agonist activity of aryl or heteroaryl substituted AMPA analogues. Synthesis and pharmacology

We have previously reported the synthesis and pharmacological characterization of analogues of 2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA, 1a), in which the methyl group was replaced by a phenyl group (APPA, 1b) or heteroaryl groups. While 2b and its 3-pyridyl analogue 2-amino-3-[3-hydroxy-5-(3-pyridyl)-4-isoxazolyl]propionic acid (3-Py-AMPA, 3) show very low affinity for AMPA receptors, introduction of heteroaryl substituents containing heteroatom in the 2-position provides potent AMPA receptor agonists. We here report the synthesis and pharmacology of 2-amino-3-(3-hydroxy-5-pyrazinyl-4-isoxazolyl)propionic acid (7) (IC50 = 1.2 μM; EC50 = 11 μM), which is weaker as an AMPA agonist than AMPA (IC50 = 0.040 μM; EC50 = 3.5 μM) but comparable in potency with 2-Py-AMPA (4) (IC50 = 0.57 μM; EC50 = 7.4 μM), as determined in radioligand binding and electrophysiological experiments, respectively. The AMPA analogues 8a-c, containing 2-, 3-, or 4-methoxyphenyl substituents, respectively, and the corresponding hydroxyphenyl analogues, 9a-c, were also synthesized and evaluated pharmacologically. With the exception of 2-amino-3-[3-hydroxy-5-(2-hydroxyphenyl)-4-isoxazolyl]propionic acid (9a), which is a very weak AMPA agonist (IC50 = 45 μM; EC50 = 324 μM), none of these compounds showed detectable effect at AMPA receptors.