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The optimization of 3,5-dimethylisoxazole derivatives to develop potent inhibitors of the BET (bromodomain and extra terminal domain) bromodomain family with good ligand efficiency. It has hypoglycemic activity.
Hewings DS; Fedorov O; Filippakopoulos P.; Martin S.; Picaud S.; Tumber A.; Wells C.; Olcina MM.; Freeman K.; Gill A.; Ritchie AJ.; Sheppard DW.; Russell AJ.; Hammond EM; Knapp S; Brennan PE; Conway SJ.Optimization of 3,5-dimethylisoxazole derivatives as potent bromodomain ligands. J Med Chem. 2013, 56 (8), 3217-27.
William E. Dulin; George C. Gerritsen. Hypoglycemic Activity of 3,5 Dimethylisoxazole. Exp Biol Med. 1963, 113 (3), 683-685.
Lithiation occurs first at the 5-methyl group. Subsequent reaction with electrophiles can be followed by further lithiation of the 3-methyl, providing a route to substituted isoxazoles, and also to 1,3-diketones by acid hydrolysis or ß-aminoketones by hydrogenolysis: Tetrahedron Lett., 22, 3699 (1981):
Review: Reaction of 3,5-dimethylisoxazole with some electrophiles: Heterocycles, 6, 805 (1977).
Hazard Statements: H226
Flammable liquid and vapour.
Precautionary Statements: P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant