192440-07-6

Basic information

• Product Name: Propanedioic acid, (acetylamino)[[3-ethoxy-5-(phenylmethyl)-4-isoxazolyl]methyl]-, diethyl ester
• CAS NO: 192440-07-6
• Molecular Formula: C22H28N2O7
• Molecular Weight: 432.474
• Mol File: 192440-07-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, (acetylamino)[[3-ethoxy-5-(phenylmethyl)-4-isoxazolyl]methyl]-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, (acetylamino)[[3-ethoxy-5-(phenylmethyl)-4-isoxazolyl]methyl]-, diethyl ester(192440-07-6)
• EPA Substance Registry System: Propanedioic acid, (acetylamino)[[3-ethoxy-5-(phenylmethyl)-4-isoxazolyl]methyl]-, diethyl ester(192440-07-6)

Safety Data

• Hazardous Substances Data: 192440-07-6(Hazardous Substances Data)

Upstream product

• 192440-02-1 5-benzyl-3-ethoxy-4-methylisoxazol 
• 140-29-4 phenylacetonitrile 
• 2867-62-1 ethyl 2-methyl-3-oxo-4-phenylbutanoate 
• 192440-04-3 5-Benzyl-4-bromomethyl-3-ethoxy-isoxazole 
• 192440-01-0 5-Benzyl-4-methyl-isoxazol-3-ol 

Relevant articles and documents

Excitatory amino-acid receptor agonists. Synthesis and pharmacology of analogues of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic acid.

We have previously proposed the existence of a lipophilic cavity of the 2-amino-3-(3 -hydroxy-5 -methylisoxazol-4-yl)propionic acid (AMPA) receptor recognition site capable of accommodating alkyl substituents of limited size in the 5-position of the isoxazole ring. In order to indirectly elucidate the approximate extent of this proposed cavity we have synthesized and pharmacologically characterized a number of AMPA analogues. For most of these AMPA analogues, a positive correlation between AMPA receptor affinity and agonist effect was observed. The only exception was demethyl-AMPA (8a), which showed relatively high AMPA receptor affinity (IC50, = 0.27 μM) but remarkably weak agonist potency (EC50 = 900 μM). Whereas the ethyl analogue of AMPA (Et-AMPA) (IC50 = 0.030 μM; EC50 = 2.3 μM) has previously been shown to be slightly more potent than AMPA (IC50 = 0.040 μM; EC50 = 3.5 μM), substitutions of a propyl or a butyl group for the methyl group of AMPA to give 8b IC50 = 0.090 μM; EC50 = 5.0 μM) or 8f (IC50 = 1.0 μM; EC50 = 32 μM), respectively, result in progressive loss of the AMPA agonist effect. Analogues containing larger groups, such as isopentyl (8e), 1-propylbutyl (8g), 2,2-dimethylpropyl (8h), or benzyl (14) groups, were very weak or totally inactive as AMPA receptor ligands.