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SJ10542 - CAS 2789678-92-6

Inquiry

SJ10542 is a potent and selective JAK2/3 directing phenyl glutarimide (PG)-PROTAC with DC50s of 14, 11 and 24 nM for JAK2, JAK3 and JAK2-fusion ALL, respectively. It utilizes a PG ligand as the cereblon (CRBN) recruiter.

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Molecular Formula

C41H46N12O5S

Molecular Weight

818.95

SJ10542

- Specification
  - IUPAC Name
    
    4-[[4-[1-[3-(cyanomethyl)-1-ethylsulfonylazetidin-3-yl]pyrazol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-2-yl]amino]-N-[3-[4-[4-(2,6-dioxopiperidin-3-yl)phenyl]piperazin-1-yl]propyl]benzamide
    
    Synonyms
    
    4-((4-(1-(3-(Cyanomethyl)-1-(ethylsulfonyl)azetidin-3-yl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-N-(3-(4-(4-(2,6-dioxopiperidin-3-yl)phenyl)piperazin-1-yl)propyl)benzamide; Benzamide, 4-[[4-[1-[3-(cyanomethyl)-1-(ethylsulfonyl)-3-azetidinyl]-1H-pyrazol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-2-yl]amino]-N-[3-[4-[4-(2,6-dioxo-3-piperidinyl)phenyl]-1-piperazinyl]propyl]-; 4-[[4-[1-[3-(Cyanomethyl)-1-(ethylsulfonyl)-3-azetidinyl]-1H-pyrazol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-2-yl]amino]-N-[3-[4-[4-(2,6-dioxo-3-piperidinyl)phenyl]-1-piperazinyl]propyl]benzamide
- Properties
  - Density
    
    1.48±0.1 g/cm3
    
    InChI Key
    
    WBEBZVDAHMXWJN-UHFFFAOYSA-N
    
    InChI
    
    InChI=1S/C41H46N12O5S/c1-2-59(57,58)52-26-41(27-52,15-16-42)53-25-30(24-45-53)36-34-14-18-43-37(34)49-40(48-36)46-31-8-4-29(5-9-31)38(55)44-17-3-19-50-20-22-51(23-21-50)32-10-6-28(7-11-32)33-12-13-35(54)47-39(33)56/h4-11,14,18,24-25,33H,2-3,12-13,15,17,19-23,26-27H2,1H3,(H,44,55)(H,47,54,56)(H2,43,46,48,49)
    
    Canonical SMILES
    
    CCS(=O)(=O)N1CC(C1)(CC#N)N2C=C(C=N2)C3=C4C=CNC4=NC(=N3)NC5=CC=C(C=C5)C(=O)NCCCN6CCN(CC6)C7=CC=C(C=C7)C8CCC(=O)NC8=O
- Reference Reading
  - 1. Development of Potent and Selective Janus Kinase 2/3 Directing PG-PROTACs
    
    Marisa Actis,Brandon Smart,Stanley Nithianantham,Jun J Yang,Gisele Nishiguchi,Charles G Mullighan,Jaeki Min,Jeremy Hunt,Dylan Maxwell,Yunchao Chang,Anand Mayasundari,Zoran Rankovic,Marcus Fischer,Lisa J Alcock,Jamie A Jarusiewicz ACS Med Chem Lett . 2022 Feb 21;13(3):475-482. doi: 10.1021/acsmedchemlett.1c00650.
    
    Aberrant activation of the JAK-STAT signaling pathway has been implicated in the pathogenesis of a range of hematological malignancies and autoimmune disorders. Here we describe the design, synthesis, and characterization of JAK2/3 PROTACs utilizing a phenyl glutarimide (PG) ligand as the cereblon (CRBN) recruiter. SJ10542 displayed high selectivity over GSPT1 and other members of the JAK family and potency in patient-derived ALL cells containing both JAK2 fusions and CRLF2 rearrangements.

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