Compounds > 3-(5-chlorofuran-2-yl)-5-methyl-4-phenylisoxazole
Page last updated: 2024-11-12

3-(5-chlorofuran-2-yl)-5-methyl-4-phenylisoxazole

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Description

3-(5-chlorofuran-2-yl)-5-methyl-4-phenylisoxazole: inhibits cyclooxygenase-1; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10355223
CHEMBL ID363228
SCHEMBL ID2274816
MeSH IDM000610576

Synonyms (9)

Synonym
bdbm50153040
3-(5-chloro-furan-2-yl)-5-methyl-4-phenyl-isoxazole
CHEMBL363228 ,
3-(5-chlorofuran-2-yl)-4-phenyl-5-methylisoxazole
IPAVFMUBTIUYBW-UHFFFAOYSA-N
SCHEMBL2274816
P6A ,
3-(5-chlorofuran-2-yl)-5-methyl-4-phenyl-1,2-oxazole
3-(5-chlorofuran-2-yl)-5-methyl-4-phenylisoxazole
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin G/H synthase 1Ovis aries (sheep)IC50 (µMol)26.66670.00032.177410.0000AID1067407; AID1205447; AID1499553
Prostaglandin G/H synthase 2Ovis aries (sheep)IC50 (µMol)50.00000.00101.453910.0000AID1499554
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID747913Binding affinity to human alpha1-acid glycoprotein by HPLC analysis relative to control2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID1067408Inhibition of ovine COX1 at 50 uM by peroxidase activity-based colorimetric assay2014European journal of medicinal chemistry, Mar-03, Volume: 74Selective COX-1 inhibition as a target of theranostic novel diarylisoxazoles.
AID747915Inhibition of COX-2 in human whole blood assessed as inhibition of LPS-induced plasma PGE2 level at 1000 uM by radioimmunoassay relative to control2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID747930Inhibition of COX-1 in human washed platelet assessed as inhibition of 0.5 uM arachidonic acid-induced TXB2 formation at 0.01 to 100 uM incubated for 25 mins prior to arachidonic acid challenge measured after 30 mins by radioimmunoassay2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID1067402Inhibition of human monocyte COX2 by whole blood assay2014European journal of medicinal chemistry, Mar-03, Volume: 74Selective COX-1 inhibition as a target of theranostic novel diarylisoxazoles.
AID1499554Inhibition of recombinant ovine COX2 catalytic activity using arachidonic acid as substrate preincubated for 5 mins followed by substrate and hemin addition measured after 2 mins by colorimetric method2017European journal of medicinal chemistry, Sep-29, Volume: 138Structural basis for selective inhibition of Cyclooxygenase-1 (COX-1) by diarylisoxazoles mofezolac and 3-(5-chlorofuran-2-yl)-5-methyl-4-phenylisoxazole (P6).
AID242103In vitro inhibitory concentration against Prostaglandin G/H synthase 2 in human whole blood assay2004Journal of medicinal chemistry, Sep-23, Volume: 47, Issue:20
Novel synthesis of 3,4-diarylisoxazole analogues of valdecoxib: reversal cyclooxygenase-2 selectivity by sulfonamide group removal.
AID1067407Inhibition of ovine COX1 by peroxidase activity-based colorimetric assay2014European journal of medicinal chemistry, Mar-03, Volume: 74Selective COX-1 inhibition as a target of theranostic novel diarylisoxazoles.
AID747916Selectivity ratio of IC50 for COX-2 in human whole blood to COX-1 in human whole blood2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID747928Inhibition of COX-1 in human THP1 cells assessed as inhibition of arachidonic acid-induced TXB2 formation at 100 uM incubated for 30 mins prior to arachidonic acid challenge measured after 30 mins by radioimmunoassay relative to vehicle-treated control2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID747924Reversible inhibition of COX-1 in human MDA-MB-231 cells assessed as inhibition of arachidonic acid-induced PGE2 formation at 100 uM incubated for 30 mins followed by compound washout measured 30 mins post arachidonic acid challenge by radioimmunoassay2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID1499553Inhibition of ovine COX1 catalytic activity using arachidonic acid as substrate preincubated for 5 mins followed by substrate and hemin addition measured after 2 mins by colorimetric method2017European journal of medicinal chemistry, Sep-29, Volume: 138Structural basis for selective inhibition of Cyclooxygenase-1 (COX-1) by diarylisoxazoles mofezolac and 3-(5-chlorofuran-2-yl)-5-methyl-4-phenylisoxazole (P6).
AID747911Inhibition of COX-1 (unknown origin) in platelet rich plasma assessed as inhibition of arachidonic acid-induced platelet aggregation at 10 uM incubated for 5 mins prior to arachidonic acid challenge measured for 5 mins by aggregometric analysis relative t2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID747914Binding affinity to human serum albumin by HPLC analysis relative to control2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID242102In vitro inhibitory concentration against Prostaglandin G/H synthase 1 in human whole blood assay2004Journal of medicinal chemistry, Sep-23, Volume: 47, Issue:20
Novel synthesis of 3,4-diarylisoxazole analogues of valdecoxib: reversal cyclooxygenase-2 selectivity by sulfonamide group removal.
AID1205449Inhibition of ovine COX-1 assessed as inhibition of PGH2 production using arachidonic acid as substrate at 50 uM by TMPD oxidation based colorimetric assay2015European journal of medicinal chemistry, Apr-13, Volume: 94General role of the amino and methylsulfamoyl groups in selective cyclooxygenase(COX)-1 inhibition by 1,4-diaryl-1,2,3-triazoles and validation of a predictive pharmacometric PLS model.
AID747929Inhibition of COX-1 in human washed platelet assessed as rightward shift in 10 uM arachidonic acid-induced TXB2 formation at 0.01 to 100 uM incubated for 25 mins prior to arachidonic acid challenge measured after 30 mins by radioimmunoassay2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID1205453Inhibition of LPS-induced COX2 in human whole blood assessed as reduction in PGH2 levels by radioimmunoassay2015European journal of medicinal chemistry, Apr-13, Volume: 94General role of the amino and methylsulfamoyl groups in selective cyclooxygenase(COX)-1 inhibition by 1,4-diaryl-1,2,3-triazoles and validation of a predictive pharmacometric PLS model.
AID1205454Inhibition of LPS-induced COX1 in human whole blood assessed as reduction in TXB2 levels by radioimmunoassay2015European journal of medicinal chemistry, Apr-13, Volume: 94General role of the amino and methylsulfamoyl groups in selective cyclooxygenase(COX)-1 inhibition by 1,4-diaryl-1,2,3-triazoles and validation of a predictive pharmacometric PLS model.
AID747910Inhibition of COX-1 (unknown origin) in platelet rich plasma assessed as inhibition of arachidonic acid-induced platelet aggregation at 30 uM incubated for 5 mins prior to arachidonic acid challenge measured for 5 mins by aggregometric analysis relative t2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID1067405Inhibition of ovine COX2 at 50 uM by peroxidase activity-based colorimetric assay2014European journal of medicinal chemistry, Mar-03, Volume: 74Selective COX-1 inhibition as a target of theranostic novel diarylisoxazoles.
AID1205447Inhibition of ovine COX-1 assessed as inhibition of PGH2 production using arachidonic acid as substrate by TMPD oxidation based colorimetric assay2015European journal of medicinal chemistry, Apr-13, Volume: 94General role of the amino and methylsulfamoyl groups in selective cyclooxygenase(COX)-1 inhibition by 1,4-diaryl-1,2,3-triazoles and validation of a predictive pharmacometric PLS model.
AID747926Reversible inhibition of COX-1 in human THP1 cells assessed as inhibition of arachidonic acid-induced TXB2 formation at 100 uM incubated for 30 mins followed by compound washout measured 30 mins post arachidonic acid challenge by radioimmunoassay2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID747934Inhibition of COX-1 (unknown origin) in platelet rich plasma assessed as inhibition of collagen-induced TXB2 formation incubated for 5 mins prior to collagen challenge measured for 5 mins by aggregometric analysis2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID747917Inhibition of COX-2 in human whole blood assessed as inhibition of LPS-induced plasma PGE2 level by radioimmunoassay2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID1499555Selectivity ratio of IC50 for recombinant ovine COX2 catalytic activity to IC50 for ovine COX1 catalytic activity2017European journal of medicinal chemistry, Sep-29, Volume: 138Structural basis for selective inhibition of Cyclooxygenase-1 (COX-1) by diarylisoxazoles mofezolac and 3-(5-chlorofuran-2-yl)-5-methyl-4-phenylisoxazole (P6).
AID1067403Inhibition of human platelet COX1 by whole blood assay2014European journal of medicinal chemistry, Mar-03, Volume: 74Selective COX-1 inhibition as a target of theranostic novel diarylisoxazoles.
AID747936Inhibition of COX-1 (unknown origin) in platelet rich plasma assessed as inhibition of collagen-induced platelet aggregation at 30 uM incubated for 5 mins prior to collagen challenge measured for 5 mins by aggregometric analysis relative to vehicle-treate2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID747918Inhibition of COX-1 in human whole blood assessed as inhibition of serum TXB2 level after 1 hr by radioimmunoassay2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID747935Inhibition of COX-1 (unknown origin) in platelet rich plasma assessed as inhibition of arachidonic acid-induced TXB2 formation incubated for 5 mins prior to arachidonic acid challenge measured for 5 mins by aggregometric analysis2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
AID747925Inhibition of COX-1 in human MDA-MB-231 cells assessed as inhibition of arachidonic acid-induced PGE2 formation at 100 uM incubated for 30 mins prior to arachidonic acid challenge measured after 30 mins by radioimmunoassay relative to vehicle-treated cont2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (16.67)29.6817
2010's5 (83.33)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.79

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.79 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.79)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
aspirin
Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.		2.0810benzoic acids;
phenyl acetates;
salicylates		anticoagulant;
antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
EC 1.1.1.188 (prostaglandin-F synthase) inhibitor;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
plant activator;
platelet aggregation inhibitor;
prostaglandin antagonist;
teratogenic agent
celecoxib
[no description available]		2.110organofluorine compound;
pyrazoles;
sulfonamide;
toluenes		cyclooxygenase 2 inhibitor;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug
ibuprofen
Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine		2.0810monocarboxylic acidantipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
environmental contaminant;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
radical scavenger;
xenobiotic
indomethacin
Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.		2.4920aromatic ether;
indole-3-acetic acids;
monochlorobenzenes;
N-acylindole		analgesic;
drug metabolite;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
gout suppressant;
non-steroidal anti-inflammatory drug;
xenobiotic metabolite;
xenobiotic
mofezolac
mofezolac: Cyclooxygenase 1 inhibitor; structure in first source; RN from Toxlit		7.5320methoxybenzenes
isoxazoles
Isoxazoles: 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.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.		8.5920isoxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
valdecoxib
[no description available]		2.0210isoxazoles;
sulfonamide		antipyretic;
antirheumatic drug;
cyclooxygenase 2 inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug
sc 560
SC560 : A member of the class of pyrazoles that is 1H-pyrazole which is substituted at positions 1, 3 and 5 by 4-methoxyphenyl, trifluoromethyl and 4-chlorophenyl groups, respectively. Unlike many members of the diaryl heterocycle class of cyclooxygenase (COX) inhibitors, SC-560 is selective for COX-1.		2.5120aromatic ether;
monochlorobenzenes;
organofluorine compound;
pyrazoles		angiogenesis modulating agent;
antineoplastic agent;
apoptosis inducer;
cyclooxygenase 1 inhibitor;
non-steroidal anti-inflammatory drug
fk 881
3-methoxy-1,5-bis(4-methoxyphenyl)-1H-1,2,4-triazole: structure in first source		2.1110
ConditionIndicatedRelationship StrengthStudiesTrials
Labor, Premature
[description not available]		02.9710
Benign Neoplasms
[description not available]		02.9710
Nervous System Disorders
[description not available]		02.9710
Ache
[description not available]		02.9710
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.9710
Nervous System Diseases
Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.		02.9710
Pain
An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.		02.9710
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.9710