192440-02-1

Basic information

• Product Name: Isoxazole, 3-ethoxy-4-methyl-5-(phenylmethyl)- (9CI)
• Synonyms: Isoxazole, 3-ethoxy-4-methyl-5-(phenylmethyl)- (9CI);3-ethoxy-4-methyl-5-(phenylmethyl)Isoxazole
• CAS NO: 192440-02-1
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.2637
• Product Categories: ETHOXY
• Mol File: 192440-02-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 340.9±37.0 °C(Predicted)
• Appearance: /
• Density: 1.077±0.06 g/cm3(Predicted)
• PKA: -2.20±0.50(Predicted)
• CAS DataBase Reference: Isoxazole, 3-ethoxy-4-methyl-5-(phenylmethyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Isoxazole, 3-ethoxy-4-methyl-5-(phenylmethyl)- (9CI)(192440-02-1)
• EPA Substance Registry System: Isoxazole, 3-ethoxy-4-methyl-5-(phenylmethyl)- (9CI)(192440-02-1)

Safety Data

• Hazardous Substances Data: 192440-02-1(Hazardous Substances Data)

Upstream product

• 140-29-4 phenylacetonitrile 
• 2867-62-1 ethyl 2-methyl-3-oxo-4-phenylbutanoate 
• 74-96-4 ethyl bromide 
• 192440-01-0 5-Benzyl-4-methyl-isoxazol-3-ol 

Downstream Products

• 192440-07-6 2-Acetylamino-2-(5-benzyl-3-ethoxy-isoxazol-4-ylmethyl)-malonic acid diethyl ester 
• 192440-04-3 5-Benzyl-4-bromomethyl-3-ethoxy-isoxazole 

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.