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SJF620 - CAS 2376187-16-3

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SJF620 is a PROTAC linked by ligands for Cereblon and Btk with a DC50 of 7.9 nM. SJF620 contains a lenalidomide analog that can recruit CRBN.

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Molecular Formula

C41H44N8O7

Molecular Weight

760.84

SJF620

- Specification
  - Related CAS
    
    2821938-05-8 (hydrochloride)
    
    Purity
    
    ≥98%
    
    Solubility
    
    Soluble in DMSO
    
    Storage
    
    Store at -20°C
    
    IUPAC Name
    
    3-[6-[2-[2-[2-[4-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]ethoxy]ethoxy]ethoxy]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione
    
    Synonyms
    
    3-(5-{2-[2-(2-{4-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}ethoxy)ethoxy]ethoxy}-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-2,6-piperidinedione; 2,6-Piperidinedione, 3-[5-[2-[2-[2-[4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl]ethoxy]ethoxy]ethoxy]-1,3-dihydro-1-oxo-2H-isoindol-2-yl]-
- Properties
  - Boiling Point
    
    988.1±65.0°C at 760 mmHg
    
    Density
    
    1.4±0.1 g/cm3
    
    InChI Key
    
    UJJYPBWMGIPXOE-UHFFFAOYSA-N
    
    InChI
    
    InChI=1S/C41H44N8O7/c42-38-36-37(27-6-8-31(9-7-27)56-30-4-2-1-3-5-30)46-49(39(36)44-26-43-38)29-14-16-47(17-15-29)18-19-53-20-21-54-22-23-55-32-10-11-33-28(24-32)25-48(41(33)52)34-12-13-35(50)45-40(34)51/h1-11,24,26,29,34H,12-23,25H2,(H2,42,43,44)(H,45,50,51)
    
    Canonical SMILES
    
    C1CC(=O)NC(=O)C1N2CC3=C(C2=O)C=CC(=C3)OCCOCCOCCN4CCC(CC4)N5C6=NC=NC(=C6C(=N5)C7=CC=C(C=C7)OC8=CC=CC=C8)N
- Reference Reading
  - 1. Design, synthesis and biological evaluation of Proteolysis Targeting Chimeras (PROTACs) as a BTK degraders with improved pharmacokinetic properties
    
    Alexandru D Buhimschi, Craig M Crews, Momar Toure, John Hines, Saul Jaime-Figueroa Bioorg Med Chem Lett . 2020 Feb 1;30(3):126877. doi: 10.1016/j.bmcl.2019.126877.
    
    A new series of Proteolysis Targeting Chimeras (PROTACs) targeting Bruton's Tyrosine Kinase (BTK) was synthesized, with the goal of improving the pharmacokinetic properties of our previously reported PROTAC, MT802. We recently described the ability of MT802 to induce degradation of both wild-type and C481S mutant BTK in immortalized cells and patient-derived B-lymphocytes. However, the pharmacokinetic properties of MT802 were not suitable for further in vivo development. Therefore, we undertook a systematic medicinal chemistry campaign to overcome this issue and made a series of PROTACs with structural modifications to the linker and E3-recruiting ligand; more specifically, the new PROTACs were synthesized with different von Hippel-Lindau (VHL) and cereblon (CRBN) ligands while keeping the BTK ligand and linker length constant. This approach resulted in an equally potent PROTAC, SJF620, with a significantly better pharmacokinetic profile than MT802. This compound may hold promise for further in vivo exploration of BTK degradation.

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