4-Hydroxy ThalidoMide
- CAS NO.：5054-59-1
- Empirical Formula: C13H10N2O5
- Molecular Weight: 274.23
- MDL number: MFCD03699892
- Update Date: 2026-03-13 15:00:32
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 |
New Products
Cyclopropane-1,1-dicarboxylic acid Cefuroxime EP Impurity-A N-Nitroso hydroxy Cetrizine EP Impurity-A Noradrenaline EP Impurity D/Noradrenaline Methyl Ether Cetirizine EP Impurity A/Cetirizine CBHP Impurity Lantanoprost rc B Clidinium Bromide Impurity tert-Butyl (2S)-[1-amino-3-(4-iodophenyl)-1-oxopropan-2-yl]carbamate 4-amino-2-fluoro-N- methylbenzamide 5-Chloro-3- Methyl -1,3-2-benzoxazol-2(3H)-one N-(2-chloropyrimidin-4-yl)-N,2,3- trimethyl-2H- indazol 6-amine N-Boc-1,4-butanediamine 4-Bromo-2-fluoro-N-methylbenzamide valeronitrile 3-chlorobenzyl cyanide 3,4 Dimethoxy Benzylcyanide 3,4 Diethoxy Benzylcyanide 2-Chloro Benzylcyanide 3-Hydroxypropionitrile 5-azidovalericacid 6,6'-bis(difluoromethoxy)-2,2'-bis((3,4-dimethoxypyridin-2-yl)methylsulfinyl)-1H,1'H-5,5'-bibenzo[d]imidazole (1-((2'-(2-((1-((2'-(2H-tetrazol-5-yl)biphenyl-4-yl)methyl)-2-butyl-4-chloro-1H-imidazol-5-yl)methyl)-2H-tetrazol-5-yl)biphenyl-4-yl)methyl)-2-butyl-4-chloro-1H-imidazol-5-yl)methanol (1-((2'-(1-((1-((2'-(2H-tetrazol-5-yl)biphenyl-4-yl)methyl)-2-butyl-4-chloro-1H-imidazol-5-yl)methyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-2-butyl-4-chloro-1H-imidazol-5-yl)methanol (4-Methoxyphenyl) hydrazine HydrochlorideRelated products of tetrahydrofuran
You may like
-
4-Hydroxy-6-methyl-1-(4-methylphenyl)-2naphthalenecarboxylic acid 98+View Details
101894-09-1 -
83883-25-4 98+View Details
83883-25-4 -
54598-15-1 4,5,7-Trimethyl-2(1H)-quinolinone 98+View Details
54598-15-1 -
4-(6-HYDROXYHEXYLOXY)BENZOIC ACID 83883-25-4 98+View Details
83883-25-4 -
39973-47-2 NA 98+View Details
39973-47-2 -
2357109-89-6 98+View Details
2357109-89-6 -
39973-47-2 NA 98+View Details
39973-47-2 -
2357109-89-6 98+View Details
2357109-89-6