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924202

Sigma-Aldrich

5-Amino-Thalidomide

≥95%

Synonym(s):

5-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione, C5 Pomalidomide, PROTAC® research ligand

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About This Item

Empirical Formula (Hill Notation):
C13H11N3O4
CAS Number:
Molecular Weight:
273.24
MDL number:
UNSPSC Code:
12352101
NACRES:
NA.22

ligand

thalidomide

Quality Level

Assay

≥95%

form

powder

SMILES string

O=C1C2=CC=C(N)C=C2C(=O)N1C3C(=O)NC(=O)CC3

InChI

1S/C13H11N3O4/c14-6-1-2-7-8(5-6)13(20)16(12(7)19)9-3-4-10(17)15-11(9)18/h1-2,5,9H,3-4,14H2,(H,15,17,18)

InChI key

IICWMVJMJVXCLY-UHFFFAOYSA-N

Application

5-Amino-Thalidomide is a derivative of the Cereblon (CRBN)-binding ligand thalidomide. 5-Amino-Thalidomide can be used to bind the CRBN E3 ubiquitin ligase in targeted protein degradation research or in the synthesis
of protein degraders with a C5 exit vector. This was previously listed under AMBH2D6FF88F.

Related Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

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Legal Information

PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license

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Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Repr. 1A

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Binbin Cheng et al.
European journal of medicinal chemistry, 199, 112377-112377 (2020-05-11)
Novel resorcinol diphenyl ether-based PROTACs (PROteolysis TArgeting Chimeras) were designed and evaluated for their inhibitory activity against the programmed cell death-1/programmed cell death-ligand 1 (PD-1/PD-L1) pathway and their ability to degrade PD-L1 protein. Most of the compounds displayed excellent inhibitory
George M Burslem et al.
ChemMedChem, 13(15), 1508-1512 (2018-06-06)
The immunomodulatory drugs (IMiDs) thalidomide, pomalidomide, and lenalidomide have been approved for the treatment of multiple myeloma for many years. Recently, their use as E3 ligase recruiting elements for small-molecule-induced protein degradation has led to a resurgence in interest in
Alexandru D Buhimschi et al.
Biochemistry, 57(26), 3564-3575 (2018-06-01)
Inhibition of Bruton's tyrosine kinase (BTK) with the irreversible inhibitor ibrutinib has emerged as a transformative treatment option for patients with chronic lymphocytic leukemia (CLL) and other B-cell malignancies, yet >80% of CLL patients develop resistance due to a cysteine

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