4-Hydroxy ThalidoMide
- CAS NO.:5054-59-1
- Empirical Formula: C13H10N2O5
- Molecular Weight: 274.23
- MDL number: MFCD03699892
- Update Date: 2024-10-31 20:01:59
What is 4-Hydroxy ThalidoMide?
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.
The Uses of 4-Hydroxy ThalidoMide
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.
Properties of 4-Hydroxy ThalidoMide
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) |
Safety information for 4-Hydroxy ThalidoMide
Computed Descriptors for 4-Hydroxy ThalidoMide
InChIKey | XMPJICVFSDYOEG-UHFFFAOYSA-N |
SMILES | C1(=O)C2=C(C(O)=CC=C2)C(=O)N1C1CCC(=O)NC1=O |
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