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Pyrazoles

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Definition: Azoles of two nitrogens at the 1,2 positions, next to each other, in contrast with IMIDAZOLES in which they are at the 1,3 positions.  includes pyrazolines & pyrazolidines   
Examples Betazole; 4,5-Dihydro-1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-amine; Epirizole; Indazoles; Muzolimine; Oxypurinol; Pyrazolones; Sulfaphenazole
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
1,3-diphenyl-3H-indeno(1,2,3-de)pyrazolo(3,4-b)quinoline  0   *Pyrazoles *Quinolines. J Fluoresc. 2012 Jan;22(1):81-91
N-5-(4'-methylphenyl)-2-furoyl-1H-pyrazole  0   *Pyrazoles. Chem Biol Drug Des. 2012 Jan;79(1):121-7
LCQ789  0   *Pyrazoles *Pyrimidinones. Drug Dev Ind Pharm. 2012 Feb;38(2):235-47.
5-(4-chloro-phenyl)-1-phenyl-6-(4-pyrazin-2-yl-phenyl)-1,5-dihydro-pyrazolo(3,4-d)pyrimidin-4-one  0   *Pyrazoles *Pyrimidinones. Naunyn Schmiedebergs Arch Pharmacol. 2011 Dec;384(6):565-81
5-((3,5-dichlorophenoxy)methyl)-1H-pyrazol-3(2H)-one  0   *Pyrazoles Superoxide Dismutase/antagonists & inhibitors. J Med Chem. 2012 Jan 12;55(1):515-27.
N-(5-(1-methyl-1H-pyrazol-4-yl)-napthalene-2-carbonyl)guanidine  0   *Guanidines *Pyrazoles. PLoS One. 2011;6(11):27660.
BMS-813160  0   *Triazines Pyrazoles Cardiovascular Agents. Expert Opin Ther Pat. 2011 Dec;21(12):1919-24
N-(3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazol-5-yl)-1-(beta-D-glucopyranosyl)-1H-1,2,3-triazole-4-methanamine  0   *Glucosides *Pyrazoles *Triazoles. J Agric Food Chem. 2011 Dec 14;59(23):12534-42
6-(1-(4-fluoro-2-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)-2H-1,4-benzoxazin-3(4H)-one  0   *Pyrazoles *Benzoxazines Receptors, Mineralocorticoid/antagonists & inhibitors. J Med Chem. 2011 Dec 22;54(24):8616-31.
2-(5-(3-fluorophenyl)-1H-pyrazol-3-yl)-5-methylphenol  0   *Phenols *Pyrazoles. Antimicrob Agents Chemother. 2011 Oct;55(10):4774-81.
3-tert-butyl-1-(4-chlorophenyl)-4-(4-methoxyphenyl)indeno(1,2-b)pyrazolo(4,3-e)pyridin-5(1H)-one  0   *Pyrazoles *Pyridones. Acta Crystallogr C. 2011 Dec;67(Pt 12):o479-83
3-tert-butyl-1-(4-chlorophenyl)-4-phenylindeno(1,2-b)pyrazolo(4,3-e)pyridin-5(1H)-one  0   *Pyrazoles *Pyridones. Acta Crystallogr C. 2011 Dec;67(Pt 12):o479-83
2-(1-(2-(4-chlorophenyl)-5-methylpyrazolo(1,5-a)pyrimidin-7-yl)-2-piperidinyl)ethanol  0   *Pyrazoles *Pyrimidines GABA-B Receptor Agonists. Neuropharmacology. 2011 Oct-Nov;61(5-6):957-66
N,N-(3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl)-1-(2-(methylamino)-2-oxoethyl)-1H-pyrazole-3-carboxamide  0   *Cyclobutanes *Pyrazoles Androgen Receptor Antagonists. J Med Chem. 2011 Nov 10;54(21):7693-704.
BAY 60-4552  0   *Pyrazoles *Pyrimidines Guanylate Cyclase Enzyme Activators. Eur Urol. 2011 Nov;60(5):1020-6.
3-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-4,5-dihydro-N'-methyl-4-phenyl-1H-pyrazole-1-carboximidamide  0   *Amidines *Pyrazoles Receptor, Cannabinoid, CB1/antagonists & inhibitors. J Pharm Sci. 2011 Nov;100(11):4687-99.
(3-(3-bromophenyl)-1-phenylpyrazol-4-yl)methyl carbamimidothioate  0   *Pyrazoles Thiourea/*analogs & derivatives. Mol Cancer Ther. 2011 Sep;10(9):1740-50.
2-((6-(3-amino-3-methylpiperidine-1-yl)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-5H-pyrrolo(3,2-d)pyrimidine-5-yl)methyl)-4-fluorobenzonitrile  0   *Pyrazoles *Pyrimidines Dipeptidyl-Peptidase IV Inhibitors. Bioorg Med Chem. 2011 Sep 15;19(18):5490-9.
(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)(piperidin-1-yl)methanone  0   *Piperidines *Pyrazoles Receptor, Cannabinoid, CB1/antagonists & inhibitors. Acta Pharmacol Sin. 2011 Sep;32(9):1148-58.
N-(3,5-dimethylphenyl)-1-(4-isopropylphenyl)-5-(piperidin-4-yl)-1H-pyrazole-4-carboxamide  0   *Anilides *Pyrazoles. J Med Chem. 2011 Oct 27;54(20):7193-205.
N'-(3-chlorophenylsulfonyl)-N-ethyl-4,4-dimethyl-4,5-dihydro-1H-pyrazole-1-carboxamidine  0   *Pyrazoles *Sulfonamides. J Med Chem. 2011 Oct 27;54(20):7030-54.
CAN 508  0   *Azo Compounds *Pyrazoles Cyclin-Dependent Kinase 9/antagonists & inhibitors. Eur J Med Chem. 2011 Sep;46(9):4289-94.
N1-(3-(5-(2-methyl-6-(4-methylpiperazino)-4-pyrimidinyl)amino-1H-3-pyrazolyl)phenyl)-1-benzenesulfonamide  0   *Pyrazoles *Sulfonamides. Bioorg Med Chem. 2011 Jul 15;19(14):4173-82.
7-(3-(4-(2-fluoroethoxy)phenyl)propyl)-2-(furan-2-yl)-7H-pyrazolo(4,3-e)(1,2,4)triazolo(1,5-c)pyrimidin-5-amine  0   *Pyrazoles *Pyrimidines Fluorine Radioisotopes. Nucl Med Biol. 2011 Aug;38(6):897-906.
4-(5-(4-bromophenyl)-3-(6-methyl-2-oxo-4-phenyl-1,2-dihydroquinolin-3-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-oxobutanoic acid  0   *Pyrazoles *Quinolones Receptors, N-Methyl-D-Aspartate/antagonists & inhibitors. Mol Pharmacol. 2011 Nov;80(5):782-95.
3-(4-fluorophenyl)-6,7-dimethoxy-3a,4-dihydro-3H-indeno(1,2-c)pyrazole-2-carbothioamide  0   *Indenes *Pyrazoles. Bioorg Med Chem Lett. 2011 Sep 15;21(18):5259-61.
withasomnine  0   *Pyrazoles Alkaloids. Org Lett. 2011 Aug 5;13(15):4016-9
4-(3-cyclopropyl-1-(methylsulfonylmethyl)-5-methyl-1H-pyrazol-4-yl)oxy-2,6-dimethylbenzonitrile  0   *Pyrazoles *Sulfones Receptors, Progesterone/antagonists & inhibitors. Drug Metab Dispos. 2011 Aug;39(8):1396-405.
methyl-5-amino-4-cyano-3-(methylthio)-1H-pyrazole-1-carbodithioate  0   *Nitriles *Pyrazoles *Thiocarbamates. Spectrochim Acta A Mol Biomol Spectrosc. 2011 Sep;79(5):1722-30
ramifenazone  0   *Pyrazoles. J Pharm Biomed Anal 2011 Sep 10;56(2):359-65
N,3-bis(4-fluorophenyl)-6,7-dimethoxy-3a,4-dihydro-3H-indeno(1,2-c)pyrazole-2-carboxamide  0   *Indenes *Pyrazoles. Bioorg Med Chem Lett 2011 Aug 1;21(15):4451-3
N-methyl-3-(1-(4-(piperazin-1-yl)phenyl)-5-(4'-(trifluoromethyl)-(1,1'-biphenyl)-4-yl)-1H-pyrazol-3-yl)propanamide  0   *Piperazines *Pyrazoles. J Med Chem 2011 Sep 22;54(18):6364-74
1-(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyl)-5-(2-methylamino)-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile  0   *Hydrocarbons, Halogenated *Pyrazoles Insecticides. J Econ Entomol. 2011 Aug;104(4):1364-8
2-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-ylimino)-2-(4-nitro-phenyl) acetonitrile  0   *Acetonitriles *Pyrazoles. Spectrochim Acta A Mol Biomol Spectrosc. 2011 Aug;79(3):618-24
6-(4-chlorophenyl)-4-methyl-6H-pyrazolo(3,4-c)isothiazol-3-amine  0   *Pyrazoles *Thiazoles. Drug Chem Toxicol 2011 Jul;34(3):324-31
5-amino-4-acetylamino-3-(4-methylphenylamino)1H-pyrazole  0   *Pyrazoles Furin/antagonists & inhibitors. Ukr Biokhim Zh. 2011 Jan-Feb;83(1):30-7
NIR-mbc94  0   *Norbornanes *Pyrazoles Ligands. Chem Biol 2011 May 27;18(5):563-8
NMS P937  0   *Pyrazoles *Quinazolines. Bioorg Med Chem Lett 2011 May 15;21(10):2969-74
SC-62807  0   *Pyrazoles *Sulfonamides. Bioorg Med Chem. 2011 May 1;19(9):2997-3004
3-(3-chlorophenoxymethyl)-1-(tetrahydropyran-4-yl)-1H-pyrazolo(3,4-d)pyrimidin-4-ylamine  0   *Pyrazoles *Pyrimidines Casein Kinase I/antagonists & inhibitors. J Pharmacol Exp Ther 2009 Aug;330(2):430-9
CP 671906  0   *Pyrazoles *Pyridines Receptors, Neuropeptide Y/antagonists & inhibitors. Bioorg Med Chem Lett 2011 May 1;21(9):2641-5
2,2-bis(3,5-dimethylpyrazol-1-yl)propionate  0   *Propionates *Pyrazoles Ligands. Dalton Trans. 2011 May 7;40(17):4678-86
ethyl-1-(4-(2*3*3-trichloroacrylamide)phenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate  0   *Pyrazoles. Biochem Biophys Res Commun. 2011 May 27;409(1):108-13
2-amino-4-(4-chloro-2-(2-(4-fluoro-1H-pyrazol-1-yl)ethoxy)-6-methylphenyl)-N-(2,2-difluoropropyl)-5,7-dihydro-6H-pyrrolo(3,4-d)pyrimidine-6-carboxamide  0   *Pyrazoles *Pyrimidines HSP90 Heat-Shock Proteins/antagonists & inhibitors. J Med Chem 2011 May 12;54(9):3368-85
1-(5-chloro-6-(trifluoromethoxy)-1H-benzoimidazol-2-yl)-1H-pyrazole-4-carboxylic acid  0   *Benzimidazoles *Pyrazoles Procollagen-Proline Dioxygenase/antagonists & inhibitors. Mol Pharmacol 2011 Jun;79(6):910-20
Sch 900776  0   *Pyrazoles *Pyrimidines. Mol Cancer Ther 2011 Apr;10(4):591-602
4,5-dihydropyrazole-1-carbothioamide  0   *Pyrazoles *Thioamides. Eur J Med Chem. 2011 May;46(5):1914-8
5-amino-4-cyano-1H-pyrazole  0   *Pyrazoles. Arch Pharm Res. 2010 Dec;33(12):1891-900
2-(5-(4-bromophenyl)-1-(2-chlorophenyl)-4-(methylsulfonyl)-1H-pyrazol-3-yl)-5-(1-(trifluoromethyl)cyclobutyl)-1,3,4-thiadiazole  0   *Pyrazoles *Thiadiazoles Receptor, Cannabinoid, CB1/antagonists & inhibitors. Future Med Chem 2009 Aug;1(5):947-67
2-(1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-(methylsulfonyl)-1H-pyrazol-3-yl)-5-(1-(trifluoromethyl)cyclobutyl)-1,3,4-thiadiazole  0   *Pyrazoles *Thiadiazoles Receptor, Cannabinoid, CB1/antagonists & inhibitors. Future Med Chem 2009 Aug;1(5):947-67
2-(2'-(5-ethyl-3,4-diphenyl-1H-pyrazol-1-yl)biphenyl-3-yloxy)acetic acid  0   *Biphenyl Compounds *Pyrazoles Fatty Acid-Binding Proteins/antagonists & inhibitors. Nature 2007 Jun 21;447(7147):959-65
3-(3,4-dimethylphenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide  0   *Pyrazoles *Thioamides. Bioorg Med Chem. 2010 Jul 1;18(13):4606-14
7-benzylamino-5-(2-(hydroxymethyl)propyl)amino-3-isopropyl-1(2)H-pyrazolo(4,3-d)pyrimidine  0   *Pyrazoles *Pyrimidines Cyclin-Dependent Kinases/antagonists & inhibitors. J Med Chem 2011 Apr 28;54(8):2980-93
4-(3-(4-methylphenyl)-4-cyano-1H-pyrazol-1-yl)benzenesulfonamide  0   *Pyrazoles *Sulfonamides Cyclooxygenase 2 Inhibitors. Basic Clin Pharmacol Toxicol 2011 Apr;108(4):263-73
binucleine 2  0   *Pyrazoles *Schiff Bases. ACS Chem Biol 2010 Nov 19;5(11):1015-20
N-(1-ethyl-1-(4-ethylphenyl)propyl)-2,7,7-trimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo(1,5-a)pyrimidine-3-carboxamide  0   *Pyrazoles *Pyrimidines Receptors, Calcium-Sensing/antagonists & inhibitors. Bioorg Med Chem 2011 Mar 15;19(6):1881-94
AZ12288553  0   *Pyrazoles *Sulfones. Fundam Clin Pharmacol. 2011 Apr;25(2):200-10
2-((4-(1-((11)C)methyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl)phenoxy)methyl)-quinoline  0   *Pyrazoles *Quinolines. Bioorg Med Chem. 2011 Mar 1;19(5):1666-73
5-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-2,4-imidazolidinedione  0   *Hydantoins *Pyrazoles. Chem Biol 2011 Feb 25;18(2):177-86
3-(difluoromethyl)-1-methyl-N-(1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl)pyrazole-4-carboxamide  0   *Norbornanes *Pyrazoles. Environ Toxicol Chem 2010 Dec;29(12):2702-12
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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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