2-(4-chloro-6-(2,3-dimethylphenylamino)pyrimidin-2-ylthio)octanoic acid: inhibits microsomal prostaglanding E2 synthase; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 24816385 |
| CHEMBL ID | 518038 |
| CHEBI ID | 184083 |
| MeSH ID | M0545413 |
| Synonym |
|---|
| 2-(4-chloro-6-(2,3-dimethylphenylamino)pyrimidin-2-ylthio)octanoic acid |
| ys 121 |
| ys-121 |
| bdbm24560 |
| pirinixic acid-based compound, 6a |
| 2-({4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl}sulfanyl)octanoic acid |
| chembl518038 , |
| 2-[4-chloro-6-(2,3-dimethylanilino)pyrimidin-2-yl]sulanyloctanoic acid |
| CHEBI:184083 |
| octanoic acid, 2-[[4-chloro-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl]thio]- |
| ys121 |
| gtpl5293 |
| AC-31489 |
| DTXSID00647434 |
| 2-{[4-chloro-6-(2,3-dimethylanilino)pyrimidin-2-yl]sulfanyl}octanoic acid |
| 916482-17-2 |
| Q27089274 |
| 2-[4-chloro-6-(2,3-dimethylanilino)pyrimidin-2-yl]sulfanyloctanoic acid |
| CS-0034392 |
| HY-111140 |
| AKOS040744997 |
| Class | Description |
|---|---|
| medium-chain fatty acid | Any fatty acid with a chain length of between C6 and C12. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Prostaglandin E synthase | Homo sapiens (human) | IC50 (µMol) | 7.9500 | 0.0010 | 2.0308 | 10.0000 | AID412944; AID413194 |
| Prostaglandin G/H synthase 1 | Ovis aries (sheep) | IC50 (µMol) | 0.0100 | 0.0003 | 2.1774 | 10.0000 | AID412948 |
| Polyunsaturated fatty acid 5-lipoxygenase | Homo sapiens (human) | IC50 (µMol) | 4.5400 | 0.0001 | 1.6847 | 9.3200 | AID1057567; AID1057570; AID362899; AID412945; AID413196 |
| Prostaglandin G/H synthase 2 | Homo sapiens (human) | IC50 (µMol) | 0.0100 | 0.0001 | 0.9950 | 10.0000 | AID413191 |
| Peroxisome proliferator-activated receptor gamma | Homo sapiens (human) | IC50 (µMol) | 3.6000 | 0.0050 | 1.2051 | 10.0000 | AID1184305 |
| Peroxisome proliferator-activated receptor alpha | Homo sapiens (human) | IC50 (µMol) | 1.0000 | 0.0005 | 0.8269 | 6.3100 | AID1184298 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Polyunsaturated fatty acid 5-lipoxygenase | Homo sapiens (human) | EC50 (µMol) | 4.1000 | 0.0700 | 2.8600 | 6.8000 | AID1798444 |
| Peroxisome proliferator-activated receptor gamma | Homo sapiens (human) | EC50 (µMol) | 3.6000 | 0.0000 | 0.9922 | 10.0000 | AID1183600; AID473102 |
| Peroxisome proliferator-activated receptor alpha | Homo sapiens (human) | EC50 (µMol) | 1.0000 | 0.0006 | 1.6074 | 10.0000 | AID1183597 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID412941 | Inhibition of PGES1 in human A549 cell microsome assessed as PGE2 formation at 10 uM by cell-free assay relative to control | 2008 | Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24 | Pirinixic acid derivatives as novel dual inhibitors of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase. |
| AID1183600 | Agonist activity at human PPARgamma LBD expressed in COS7 cells after 12 hrs by Dual-Glo luciferase assay | 2014 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16 | Molecular determinants for improved activity at PPARα: structure-activity relationship of pirinixic acid derivatives, docking study and site-directed mutagenesis of PPARα. |
| AID362898 | Inhibition of 5-lipoxygenase in human intact polymorphonuclear leukocytes assessed as suppression of A23187-induced product formation at 10 uM | 2008 | Journal of medicinal chemistry, Sep-11, Volume: 51, Issue:17 | Novel and potent inhibitors of 5-lipoxygenase product synthesis based on the structure of pirinixic acid. |
| AID473102 | Transactivation of human PPARgamma LBD expressed in african green monkey Cos7 cells co-transfected with fused GAL4-DBD after 14 hrs by Dual-Glo Luciferase reporter gene assay | 2010 | Bioorganic & medicinal chemistry letters, Apr-15, Volume: 20, Issue:8 | Rational design of a pirinixic acid derivative that acts as subtype-selective PPARgamma modulator. |
| AID1184298 | Activation of human PPARalpha ligand binding domain expressed in COS7 cells by luciferase reporter gene assay | 2014 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16 | Identification of pirinixic acid derivatives bearing a 2-aminothiazole moiety combines dual PPARα/γ activation and dual 5-LO/mPGES-1 inhibition. |
| AID1183597 | Agonist activity at wild-type human PPARalpha LBD expressed in COS7 cells after 12 hrs by Dual-Glo luciferase assay | 2014 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16 | Molecular determinants for improved activity at PPARα: structure-activity relationship of pirinixic acid derivatives, docking study and site-directed mutagenesis of PPARα. |
| AID1183602 | Agonist activity at human PPARdelta LBD expressed in COS7 cells at 10 uM after 12 hrs by Dual-Glo luciferase assay | 2014 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16 | Molecular determinants for improved activity at PPARα: structure-activity relationship of pirinixic acid derivatives, docking study and site-directed mutagenesis of PPARα. |
| AID412947 | Inhibition of human recombinant COX2 assessed as remaining activity at 10 uM relative to control | 2008 | Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24 | Pirinixic acid derivatives as novel dual inhibitors of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase. |
| AID412946 | Inhibition of ovine COX1 assessed as remaining activity at 10 uM relative to control | 2008 | Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24 | Pirinixic acid derivatives as novel dual inhibitors of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase. |
| AID669826 | Inhibition of mPGES-1 derived from LPS stimulated mouse RAW264.7 cells microsomal fraction using PGH2 as substrate at 5 uM preincubated for 30 mins prior to substrate addition measured after 1 min by LC-MS/MS analysis relative to control | 2012 | Journal of medicinal chemistry, Apr-26, Volume: 55, Issue:8 | Structure-activity relationship of nonacidic quinazolinone inhibitors of human microsomal prostaglandin synthase 1 (mPGES 1). |
| AID362897 | Inhibition of 5-lipoxygenase in human intact polymorphonuclear leukocytes assessed as suppression of A23187-induced product formation at 1 uM | 2008 | Journal of medicinal chemistry, Sep-11, Volume: 51, Issue:17 | Novel and potent inhibitors of 5-lipoxygenase product synthesis based on the structure of pirinixic acid. |
| AID413194 | Inhibition of mPGES1 in human A549 cells assessed as inhibition of IL-1-beta-induced PGE2 formation by cell-intact assay | 2008 | Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24 | Pirinixic acid derivatives as novel dual inhibitors of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase. |
| AID669827 | Inhibition of mPGES-1 derived from LPS stimulated mouse NIH3T3 cells microsomal fraction using PGH2 as substrate at 5 uM preincubated for 30 mins prior to substrate addition measured after 1 min by LC-MS/MS analysis relative to control | 2012 | Journal of medicinal chemistry, Apr-26, Volume: 55, Issue:8 | Structure-activity relationship of nonacidic quinazolinone inhibitors of human microsomal prostaglandin synthase 1 (mPGES 1). |
| AID1184305 | Activation of human PPARgamma ligand binding domain expressed in COS7 cells by luciferase reporter gene assay | 2014 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16 | Identification of pirinixic acid derivatives bearing a 2-aminothiazole moiety combines dual PPARα/γ activation and dual 5-LO/mPGES-1 inhibition. |
| AID412944 | Inhibition of PGES1 in human A549 cell microsome assessed as PGE2 formation by cell-free assay | 2008 | Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24 | Pirinixic acid derivatives as novel dual inhibitors of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase. |
| AID412948 | Inhibition of ovine COX1 | 2008 | Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24 | Pirinixic acid derivatives as novel dual inhibitors of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase. |
| AID1057570 | Inhibition of 5-lipoxygenase in human polymorphonuclear leukocytes | 2013 | Journal of medicinal chemistry, Nov-27, Volume: 56, Issue:22 | Aminothiazole-featured pirinixic acid derivatives as dual 5-lipoxygenase and microsomal prostaglandin E2 synthase-1 inhibitors with improved potency and efficiency in vivo. |
| AID412945 | Inhibition of human recombinant 5-LO expressed in Escherichia coli by cell-free assay | 2008 | Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24 | Pirinixic acid derivatives as novel dual inhibitors of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase. |
| AID1183601 | Agonist activity at human PPARgamma LBD expressed in COS7 cells after 12 hrs by Dual-Glo luciferase assay relative to pioglitazone | 2014 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16 | Molecular determinants for improved activity at PPARα: structure-activity relationship of pirinixic acid derivatives, docking study and site-directed mutagenesis of PPARα. |
| AID1057567 | Inhibition of 5-lipoxygenase in A23187-stimulated human polymorphonuclear leukocytes using arachidonic acid as substrate incubated 15 mins prior to substrate addition measured after 10 mins by HPLC analysis | 2013 | Journal of medicinal chemistry, Nov-27, Volume: 56, Issue:22 | Aminothiazole-featured pirinixic acid derivatives as dual 5-lipoxygenase and microsomal prostaglandin E2 synthase-1 inhibitors with improved potency and efficiency in vivo. |
| AID413196 | Inhibition of 5-LO in PMNL cells | 2008 | Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24 | Pirinixic acid derivatives as novel dual inhibitors of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase. |
| AID1183598 | Agonist activity at wild-type human PPARalpha LBD expressed in COS7 cells after 12 hrs by Dual-Glo luciferase assay relative to pirinixic acid | 2014 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16 | Molecular determinants for improved activity at PPARα: structure-activity relationship of pirinixic acid derivatives, docking study and site-directed mutagenesis of PPARα. |
| AID362899 | Inhibition of 5-lipoxygenase in human intact polymorphonuclear leukocytes assessed as suppression of A23187-induced product formation | 2008 | Journal of medicinal chemistry, Sep-11, Volume: 51, Issue:17 | Novel and potent inhibitors of 5-lipoxygenase product synthesis based on the structure of pirinixic acid. |
| AID413191 | Inhibition of human recombinant COX2 | 2008 | Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24 | Pirinixic acid derivatives as novel dual inhibitors of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase. |
| AID473103 | Transactivation of human PPARgamma LBD expressed in african green monkey Cos7 cells co-transfected with fused GAL4-DBD after 14 hrs by Dual-Glo Luciferase reporter gene assay relative to pioglitazone | 2010 | Bioorganic & medicinal chemistry letters, Apr-15, Volume: 20, Issue:8 | Rational design of a pirinixic acid derivative that acts as subtype-selective PPARgamma modulator. |
| AID1798444 | Determination of 5-LO Product Formation in Intact Cells (EC50/IC50) from Article 10.1021/jm800588x: \\Novel and potent inhibitors of 5-lipoxygenase product synthesis based on the structure of pirinixic acid.\\ | 2008 | Journal of medicinal chemistry, Sep-11, Volume: 51, Issue:17 | Novel and potent inhibitors of 5-lipoxygenase product synthesis based on the structure of pirinixic acid. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 2 (22.22) | 29.6817 |
| 2010's | 7 (77.78) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (12.27) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 9 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||