| Identification | Back Directory | [Name]
4-Hydroxy ThalidoMide | [CAS]
5054-59-1 | [Synonyms]
186942
E3 ligase Ligand 2
4-Hydroxy ThalidoMide
Thalidomide Impurity 1
Pomalidomide Impurity 15
Thalidomide 4-Hydroxy Impurity
2-(2,6-Dioxo-3-piperidinyl)-4-hydroxyisoindoline-1,3-dione
2-(2,6-dioxopiperidin-3-yl)-4-hydroxyisoindoline-1,3-dione
2-(2,6-Dioxo-piperidin-3-yl)-4-hydroxy-isoindole-1,3-dione
4-hydroxy-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
2-(2,6-dioxo-piperidine-3-yl)-4-hydroxy-isoindole-1,3-dione
1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-4-hydroxy-
2-(2,6-dioxopiperidin-3-yl)-4-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione | [Molecular Formula]
C13H10N2O5 | [MDL Number]
MFCD03699892 | [MOL File]
5054-59-1.mol | [Molecular Weight]
274.23 |
| Chemical Properties | Back Directory | [Melting point ]
273-275 °C | [Boiling point ]
568.3±45.0 °C(Predicted) | [density ]
1.611±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
DMF: 12 mg/ml; DMSO: 10 mg/ml | [form ]
A solid | [pka]
6.82±0.20(Predicted) | [color ]
White to gray | [InChI]
InChI=1S/C13H10N2O5/c16-8-3-1-2-6-10(8)13(20)15(12(6)19)7-4-5-9(17)14-11(7)18/h1-3,7,16H,4-5H2,(H,14,17,18) | [InChIKey]
XMPJICVFSDYOEG-UHFFFAOYSA-N | [SMILES]
C1(=O)C2=C(C(O)=CC=C2)C(=O)N1C1CCC(=O)NC1=O |
| Hazard Information | Back Directory | [Description]
4-Hydroxy-thalidomide is the Thalidomide-based Cereblon ligand used in the recruitment of CRBN protein. It can be connected to the ligand for protein by a linker to form PROTACs. | [Uses]
2-(2,6-Dioxopiperidin-3-yl)-4-hydroxyisoindoline-1,3-dione is an intermediate for the synthesis of dTAG-13 (D710020), which is a degradation tag which was tested for its efficiency at depleting FKBP12F36V -MELK(sg3R) and was found to have significantly degraded FKBP12F36V -MELK(sg3R) within 4 hours.Used in the study of cancer research. | [Biochem/physiol Actions]
Thalidomide hydroxylation can occur on glutarimide or phthalimide rings to yield metabolites of 4-hydroxy thalidomide. Interestingly, only metabolites phthaloyl glutamic acid and 4-hydroxy thalidomide have been tested for their anti-angiogenic activities. Hydroxylation of thalidomide on the C4-position of the phthalimide ring (4-hydroxy thalidomide) led to a weakly anti-angiogenic compound. 4-hydroxy thalidomide was not active in the CAM assay but was one of the most active compounds against HUVEC proliferation[1]. | [References]
[1] M. G. Marks. “Effects of putative hydroxylated thalidomide metabolites on blood vessel density in the chorioallantoic membrane (CAM) assay and on tumor and endothelial cell proliferation.” Biological & pharmaceutical bulletin 356 1 (2002): 597–604. |
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