2-(2,6-Dioxopiperidin-3-yl)-5-fluoro-6-(piperazin-1-yl)isoindoline-1,3-dione hydrochloride - CAS 2222114-23-8

Inquiry

2-(2,6-Dioxopiperidin-3-yl)-5-fluoro-6-(piperazin-1-yl)isoindoline-1,3-dione hydrochloride is a specialized functionalized cereblon ligand used in PROTAC (Proteolysis Targeting Chimera) technology. By incorporating modifications such as piperazine and fluorine, this compound enhances the binding affinity and stability of thalidomide towards cereblon, a key component of the E3 ubiquitin ligase complex. In PROTACs, this ligand helps recruit cereblon to target proteins, facilitating their ubiquitination and subsequent degradation by the proteasome. This targeted approach holds significant potential for developing therapies for diseases where selective protein degradation is beneficial, such as cancer and other conditions.

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Molecular Formula

C17H18ClFN4O4

Molecular Weight

396.80

2-(2,6-Dioxopiperidin-3-yl)-5-fluoro-6-(piperazin-1-yl)isoindoline-1,3-dione hydrochloride

- Specification
  - Related CAS
    
    2222114-22-7 (free base)
    
    Purity
    
    ≥95%
    
    Appearance
    
    Yellow solid
    
    Storage
    
    Store at 2-8 °C
    
    IUPAC Name
    
    2-(2,6-dioxopiperidin-3-yl)-5-fluoro-6-piperazin-1-ylisoindole-1,3-dione;hydrochloride
    
    Synonyms
    
    Thalidomide-Piperazine 5-fluoride hydrochloride; 2-(2,6-Dioxo-3-piperidyl)-5-fluoro-6-(1-piperazinyl)isoindoline-1,3-dione hydrochloride; 2-(2,6-Dioxopiperidin-3-yl)-5-fluoro-6-(piperazin-1-yl)-2,3-dihydro-1H-isoindole-1,3-dione hydrochloride; Poma-5-F-6-PipA; 2-(2,6-Dioxo-3-piperidinyl)-5-fluoro-6-(1-piperazinyl)-1H-isoindole-1,3(2H)-dione hydrochloride (1:1); 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-5-fluoro-6-(1-piperazinyl)-, hydrochloride (1:1); Pomalidomide 5'-fluoro-6'-piperazine hydrochloride
- Properties
  - InChI Key
    
    UQDWELYJNPCIGK-UHFFFAOYSA-N
    
    InChI
    
    InChI=1S/C17H17FN4O4.ClH/c18-11-7-9-10(8-13(11)21-5-3-19-4-6-21)17(26)22(16(9)25)12-1-2-14(23)20-15(12)24;/h7-8,12,19H,1-6H2,(H,20,23,24);1H
    
    Canonical SMILES
    
    C1CC(=O)NC(=O)C1N2C(=O)C3=CC(=C(C=C3C2=O)F)N4CCNCC4.Cl

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