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Isoxazoles

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Definition: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.     
Examples alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid; Cycloserine; Ibotenic Acid; Isocarboxazid
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
5-furan-2yl-isoxazole-3-carboxylic acid (3-imidazol-1yl-propyl)-amide  0   *Imidazoles *Isoxazoles. Cell Res. 2012 Jan;22(1):237-47.
3-isopropyl-2-methyl-4-methyleneisoxazolidin-5-one  0   *Isoxazoles Antineoplastic Agents. Chem Biol Drug Des. 2012 Jan;79(1):112-20
5-(2,4-dihydroxy-5-isopropylphenyl)-4-(5-(morpholinomethyl)isoxazole-3-carbonylamino)isoxazole-3-carboxylic acid ethylamide  0   *Isoxazoles *Resorcinols HSP90 Heat-Shock Proteins/antagonists & inhibitors. J Med Chem. 2011 Dec 22;54(24):8592-604.
3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-2-amine  0   *Aminopyridines *Isoxazoles. Antimicrob Agents Chemother. 2011 Oct;55(10):4543-51.
5-(N,N-dimethylaminomethyl)-3-(4-nitrophenyl)-4,5-dihydroisoxazole  0   *Isoxazoles. J Med Chem. 2011 Nov 10;54(21):7663-77.
4-(1-((5-((2,6-dimethylphenoxy)methyl)-3-isoxazolyl)carbonyl)-4-piperidinyl)pyridine  0   *Isoxazoles *Piperidines *Pyridines. Nat Chem Biol. 2011 Dec;7(12):891-3
3-(5-(4-(cyclopentyloxy)-2-hydroxybenzoyl)-2-((3-hydroxy-1,2-benzisoxazol-6-yl)methoxy)phenyl)propionic acid  0   *Benzophenones *Isoxazoles. Drug Metab Dispos. 2011 May;39(5):803-13.
3-(7-trifluoromethyl-5-(2-trifluoromethylphenyl)-1H-benzimidazol-2-yl)-1-oxa-2-azaspiro(4.5)dec-2-ene  0   *Benzimidazoles *Isoxazoles TRPM Cation Channels/antagonists & inhibitors. J Med Chem 2011 Jan 13;54(1):233-47
AZ 12253801  0   *Isoxazoles *Pyrimidines Receptor, IGF Type 1/antagonists & inhibitors. Br J Cancer 2011 Aug 23;105(5):649-57
ERW1227B  0   *Isoxazoles. J Neurooncol. 2011 Jun;103(2):207-19
N-cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide  0   *Isoxazoles *Thiophenes. Differentiation 2011 Apr;81(4):233-42
UTL-5g compound  0   *Isoxazoles. J Exp Ther Oncol. 2011;9(2):129-37
3-(4-piperidyl)-6-fluoro-1,2-benzisoxazole  0   *Isoxazoles *Piperidines. Eur J Med Chem. 2011 Feb;46(2):704-11
methyl 4-chloro-5-phenylisoxazole-3-carboxylate  0   *Isoxazoles. J Phys Chem A. 2011 Feb 24;115(7);1199-209
GSK 2324  0   *Isoxazoles *Quinolines. Bioorg Med Chem Lett 2011 Feb 15;21(4):1206-13
3-bromoacivicin  0   *Isoxazoles. ChemMedChem. 2011 Feb 7;6(2):329-33
psammaplysin H  0   *Isoxazoles *Oxepins. Bioorg Med Chem Lett 2011 Jan 15;21(2):846-8
KST 5468  0   *Isoxazoles *Piperazines. Pharmacol Biochem Behav 2010 Dec;97(2):198-204
1-(2-(isoxazol-3-yl)-1H-imidazol-4-yl)butane-1,2,3,4-tetraol  0   *Imidazoles *Isoxazoles. J Med Chem 2010 Dec 23;53(24):8650-62
SC 791  0   *Isoxazoles *Sulfonamides Cyclooxygenase 2. J Pharmacol Exp Ther 2003 Mar;304(3):959-67
5-isoxazoyl-cyclohexylalanyl-isoleucyl-spiroindane-1,4'-piperidine  0   *Dipeptides *Isoxazoles Receptor, PAR-2/antagonists & inhibitors. J Med Chem 2010 Oct 28;53(20):7428-40
5-isoxazoyl-cyclohexylalanyl-isoleucyl-(3-(aminomethyl)phenyl)-(4-(aminomethyl)piperidin-1-yl)methanone  0   *Isoxazoles *Oligopeptides Receptor, PAR-2/agonists. J Med Chem 2010 Oct 28;53(20):7428-40
3-3'-isoxazole-3,5-diylbis(5-methoxy-1-methyl-1H-indole)  0   *Indoles *Isoxazoles. Bioorg Med Chem 2010 Jun 15;18(12):4524-9
3-ethyl-4-(4-methylisoxazol-5-yl)-5-(methylthio)thiophene-2-carboxamide  0   *Isoxazoles *Thiophenes. Int J Pharm 2010 Jun 15;392(1-2):42-50
(N-methyl-(11)C) 5-methyl-3-(4-(3-phenylallyl)-piperazin-1-ylmethyl)-3,3a,4,5-tetrahydroisoxazolo(4,3-c)quinoline  0   *Isoxazoles *Quinolines Carbon Radioisotopes. Bioorg Med Chem Lett. 2010 Jun 15;20(12):3654-7
5-phenylisoxazole-3-carboxylic acid  0   *Carboxylic Acids *Isoxazoles. Eur J Med Chem. 2010 Jun;45(6):2663-70
19-hydroxyaraplysillin-I N(20)-sulfamate  0   *Hydrocarbons, Brominated *Isoxazoles. J Nat Prod. 2009 Feb 27;72(2):290-4
araplysillin-I N(20)-sulfamate  0   *Hydrocarbons, Brominated *Isoxazoles. J Nat Prod. 2009 Feb 27;72(2):290-4
paliperidone palmitate  0   *Isoxazoles *Palmitates. Curr Med Res Opin 2010 Feb;26(2):377-87INVEGA SUSTENNA
(N-(4-chlorophenyl))-alpha-((4-chlorophenyl)-aminomethylene)-3-methyl-5-isoxazoleacet-amide  0   *Isoxazoles. Br J Pharmacol. 2009 Dec;158(8):1857-64
N-acetyl-N-(4-(4-methoxyphenyl-3-(3,4,5-trimethoxyphenyl)isoxazol-5-yl)acetamide)  0   *Acetamides *Isoxazoles. Cancer Lett. 2009 Nov 18;285(1):13-22
3-pyrazolyl-4,5-dicarbethoxy isoxazole  0   *Isoxazoles *Pyrazoles. Bioorg Med Chem Lett. 2009 Jul 1;19(13):3370-3
CX717  0   *Isoxazoles. Psychopharmacology (Berl). 2009 Jan;202(1-3):355-69
2-butyl-4-chloro-5-formyl-1-((3-(2-methoxyphenyl)isoxazolyl-5-methyl))imidazole  0   *Imidazoles *Isoxazoles Receptor, Angiotensin, Type 1. Yao Xue Xue Bao 2007 Aug;42(8):822-7
3beta-(4-methylphenyl)-2beta-(3-(4-chlorophenyl)isoxazol-5-yl)tropane  0   *Isoxazoles *Tropanes. Br J Pharmacol. 2009 Apr;156(7):1178-84
(S)-2-ethoxy-3-(4-(5-(4-(5-(methoxymethyl)isoxazol-3-yl)phenyl)-3-methylthiophen-2-yl)methoxyphenyl)propanoic acid  0   *Isoxazoles *Propionic Acids *Thiophenes. Arch Pharm Res 2009 May;32(5):721-7
RM11 compound  0   *Isoxazoles. Pharmacol Rep 2008 Mar-Apr;60(2):183-9
5-ketoclomazone  0   *Isoxazoles *Oxazolidinones. Pest Manag Sci 2008 Oct;64(10):1031-9
LY 402913  0   *Isoxazoles *Quinolones. J Mol Model 2008 Oct;14(10):911-21
5-chlorobenzo(d)isoxazol-3-ol  0   *Isoxazoles. J Med Chem 2008 Jun 26;51(12):3357-9
N-hydroxy-valdecoxib  0   *Isoxazoles *Sulfonamides. Bioorg Med Chem 2008 May 1;16(9):5322-30
ABIO 0801  0   *Isoxazoles. Hum Psychopharmacol 2008 Apr;23(3):243-54
tricholomic acid  0   *Isoxazoles Glycine/*analogs & derivatives Receptors, AMPA/agonists Receptors, Kainic Acid/agonists Receptors, Metabotropic Glutamate/agonists. J Med Chem 2008 Apr 10;51(7):2311-5
1-(4-(3-amino-7-methoxybenzo(d)isoxazol-4-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea  0   *Isoxazoles *Phenylurea Compounds Receptor Protein-Tyrosine Kinases/antagonists & inhibitors. J Med Chem 2008 Mar 13;51(5):1231-41
5-(2,4-dihydroxy-5-isopropylphenyl)-4-(4-morpholin-4-ylmethylphenyl)isoxazole-3-carboxylic acid ethylamide  0   *Isoxazoles *Resorcinols HSP90 Heat-Shock Proteins/antagonists & inhibitors. J Med Chem 2008 Jan 24;51(2):196-218
N-(4-chlorophenyl)-3-carboxyamidyl-5-methylisoxazole  0   *Isoxazoles. Br J Dermatol 2007 Sep;157(3):575-9
2-(butyryl-(2'-(4-fluoro-5-methylisoxazol-3-ylsulfamoyl)biphenyl-4-ylmethyl)amino)-N-isopropyl-3-methylbutyramide  0   *Isoxazoles *Sulfonamides Receptors, Angiotensin/antagonists & inhibitors Receptor, Endothelin A/antagonists & inhibitors. Drug Metab Dispos 2007 May;35(5):795-805
2-(butyryl-(2'-(4-chloro-5-methylisoxazol-3-ylsulfamoyl)biphenyl-4-ylmethyl)amino)-N-isopropyl-3-methylbutyramide  0   *Isoxazoles *Sulfonamides Receptors, Angiotensin/antagonists & inhibitors Receptor, Endothelin A/antagonists & inhibitors. Drug Metab Dispos 2007 May;35(5):795-805
2-(butyryl-(2'-(4,5-dimethylisoxazol-3-ylsulfamoyl)biphenyl-4-ylmethyl)amino)-N-isopropyl-3-methylbutyramide  0   *Isoxazoles *Sulfonamides Receptors, Angiotensin/antagonists & inhibitors Receptor, Endothelin A/antagonists & inhibitors. Drug Metab Dispos 2007 May;35(5):795-805
2-tert-butyl-4-(4-phenyl-isoxazol-3-ylmethoxy)-phenol  0   *Isoxazoles *Phenols. J Pharm Pharmacol 2007 Jun;59(6):829-35
N-((5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro(4.5)deca-2,6,8-triene-3-carboxy)-4-aminobutanoic acid  0   *Hydrocarbons, Brominated *Isoxazoles. J Nat Prod 2007 Jul;70(7):1191-4
araplysillin N9-sulfamate  0   *Hydrocarbons, Brominated *Isoxazoles. J Nat Prod 2007 Jul;70(7):1191-4
VER-50589  0   *Isoxazoles. Mol Cancer Ther 2007 Apr;6(4):1198-211
5-methyl-3-phenyl-6-(4-(2-methoxyethoxymethyl)phenyl)isoxazolo(5,4-c)pyridin-5H-4-one  0   *Isoxazoles *Pyridones. Bioorg Med Chem Lett 2007 Jan 1;17(1):193-6
N-(2-chloro-4-((6,7-dimethoxy-4-quinolyl)oxy)phenyl)-N'-(5-methyl-3-isoxazolyl)urea  0   *Isoxazoles *Phenylurea Compounds Receptors, Vascular Endothelial Growth Factor/antagonists & inhibitors. Cancer Res 2006 Sep 15;66(18):9134-42
tert-butyl 3-(5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-4,5-dihydroisoxazole-3-carboxamido)butanoate  0   *Isoxazoles. J Med Chem 2006 Jul 13;49(14):4055-8
7-amino-3a,4-dihydro-3H-(1)benzopyrano(4,3-c)isoxazole  0   *Isoxazoles *Pyrans. Bioorg Med Chem. 2006 Jul 1;14(13):4361-72
2-((5,7-dipropyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl)oxy)-2-methylpropanoic acid  0   *Isoxazoles *Propionic Acids. J Org Chem 2005 Oct 14;70(21):8560-3
EF1502  0   *Isoxazoles. Neurochem Int 2006 May-Jun;48(6-7):637-42
KCC 009  0   *Isoxazoles. FEBS Lett 2006 Apr 17;580(9):2351-7
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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012
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