4-Hydroxy ThalidoMide
4-Hydroxy ThalidoMide Basic information
- Product Name:
- 4-Hydroxy ThalidoMide
- Synonyms:
-
- 4-Hydroxy ThalidoMide
- 2-(2,6-dioxopiperidin-3-yl)-4-hydroxyisoindoline-1,3-dione
- 2-(2,6-Dioxo-piperidin-3-yl)-4-hydroxy-isoindole-1,3-dione
- 2-(2,6-dioxopiperidin-3-yl)-4-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione
- E3 ligase Ligand 2
- Pomalidomide Impurity 15
- 2-(2,6-Dioxo-3-piperidinyl)-4-hydroxyisoindoline-1,3-dione
- Thalidomide Impurity 1
- CAS:
- 5054-59-1
- MF:
- C13H10N2O5
- MW:
- 274.23
- Mol File:
- 5054-59-1.mol
4-Hydroxy ThalidoMide Chemical Properties
- Melting point:
- 273-275 °C
- Boiling point:
- 568.3±45.0 °C(Predicted)
- Density
- 1.611±0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 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
4-Hydroxy ThalidoMide Usage And Synthesis
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.
4-Hydroxy ThalidoMideSupplier
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4-Hydroxy ThalidoMide(5054-59-1)Related Product Information
- L-Prolinamide, 3-methyl-L-valyl-4-hydroxy-N-[(1S)-1-[4-(4-methyl-5-thiazolyl)phenyl]ethyl]-, (4R)-
- Pomalidomide-d5
- DL-Glutamine
- 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
- (S)-Pomalidomide
- 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
- Thalidomide
- (R)-Pomalidomide
- Pomalidomide Impurity 4
- Pomalidomide Impurity 3
- Pomalidomide Impurity 6
- Pomalidomide
- Pomalidomide Impurity 10
- Pomalidomide Impurity 2
- 3-Nitrophthalic acid
- 3-AMINOPHTHALIC ACID
- 2-(2,6-dioxopiperidin-3-yl)-4-(hydroxyamino)isoindoline-1,3-dione
- 3,4-Diamino-4-oxobutyric acid