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PROTAC RIPK degrader-6 - CAS 2089205-64-9

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PROTAC RIPK degrader-6 is a Cereblon-based PROTAC targeting RIP Kinase degradation wherein the RIP2 kinase inhibitor is linked via a linker to a cereblon binder.

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Molecular Formula

C43H48N6O11S2

Molecular Weight

889.00

PROTAC RIPK degrader-6

- Specification
  - Storage
    
    Store at -20°C
    
    IUPAC Name
    
    2-[2-[2-[2-[2-[4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfonylquinolin-7-yl]oxyethoxy]ethoxy]ethoxy]ethoxy]-N-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-4-yl]acetamide
    
    Synonyms
    
    Acetamide, 2-[2-[2-[2-[2-[[4-(5-benzothiazolylamino)-6-[(1,1-dimethylethyl)sulfonyl]-7-quinolinyl]oxy]ethoxy]ethoxy]ethoxy]ethoxy]-N-[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1-oxo-1H-isoindol-4-yl]-; 14-((4-(Benzo[d]thiazol-5-ylamino)-6-(tert-butylsulfonyl)quinolin-7-yl)oxy)-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)-3,6,9,12-tetraoxatetradecanamide
- Properties
  - Boiling Point
    
    1111.1±65.0°C at 760 Torr
    
    Density
    
    1.398±0.06 g/cm3
    
    InChI Key
    
    BRZGXSNAXRPPFI-UHFFFAOYSA-N
    
    InChI
    
    InChI=1S/C43H48N6O11S2/c1-43(2,3)62(54,55)38-22-29-32(46-27-7-9-37-34(21-27)45-26-61-37)11-12-44-33(29)23-36(38)60-20-19-58-16-15-56-13-14-57-17-18-59-25-40(51)47-31-6-4-5-28-30(31)24-49(42(28)53)35-8-10-39(50)48-41(35)52/h4-7,9,11-12,21-23,26,35H,8,10,13-20,24-25H2,1-3H3,(H,44,46)(H,47,51)(H,48,50,52)
    
    Canonical SMILES
    
    CC(C)(C)S(=O)(=O)C1=CC2=C(C=CN=C2C=C1OCCOCCOCCOCCOCC(=O)NC3=CC=CC4=C3CN(C4=O)C5CCC(=O)NC5=O)NC6=CC7=C(C=C6)SC=N7
- Reference Reading
  - 1. Extended pharmacodynamic responses observed upon PROTAC-mediated degradation of RIPK2.
    
    Mares, A., Miah, A.H., Smith, I.E., Rackham, M., Thawani, A.R., Cryan, J., Haile, P.A., Votta, B.J., Beal, A.M., Capriotti, C. and Reilly, M.A., 2020. Communications biology, 3(1), pp.1-13.
    
    Proteolysis-Targeting Chimeras (PROTACs) are heterobifunctional small-molecules that can promote the rapid and selective proteasome-mediated degradation of intracellular proteins through the recruitment of E3 ligase complexes to non-native protein substrates. The catalytic mechanism of action of PROTACs represents an exciting new modality in drug discovery that offers several potential advantages over traditional small-molecule inhibitors, including the potential to deliver pharmacodynamic (PD) efficacy which extends beyond the detectable pharmacokinetic (PK) presence of the PROTAC, driven by the synthesis rate of the protein. Herein we report the identification and development of PROTACs that selectively degrade Receptor-Interacting Serine/Threonine Protein Kinase 2 (RIPK2) and demonstrate in vivo degradation of endogenous RIPK2 in rats at low doses and extended PD that persists in the absence of detectable compound. This disconnect between PK and PD, when coupled with low nanomolar potency, offers the potential for low human doses and infrequent dosing regimens with PROTAC medicines.

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