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Merck
CN

SML2738

SM1-71

≥98% (HPLC)

Synonym(s):

N-[2-[[5-Chloro-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-4-pyrimidinyl]amino]phenyl]-2-propenamide

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About This Item

Empirical Formula (Hill Notation):
C24H26ClN7O
CAS Number:
2088179-99-9
Molecular Weight:
463.96
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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SMILES string

Clc1c(nc(nc1)Nc3ccc(cc3)N4CCN(CC4)C)Nc2c(cccc2)NC(=O)C=C

InChI key

SCMLGVPMSXTUNC-UHFFFAOYSA-N

InChI

1S/C24H26ClN7O/c1-3-22(33)28-20-6-4-5-7-21(20)29-23-19(25)16-26-24(30-23)27-17-8-10-18(11-9-17)32-14-12-31(2)13-15-32/h3-11,16H,1,12-15H2,2H3,(H,28,33)(H2,26,27,29,30)

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

SM1-71 is a cell penetrant and potent multi-targeted kinase inhibitor that engages kinases through both reversible and irreversible binding. SM1-71 covalently inhibits 23 kinases including MKNK2, MAP2K1/2/3/4/6/7, GAK, AAK1, BMP2K, MAP3K7, MAPKAPK5, GSK3A/B, MAPK1/3, SRC, YES1, FGFR1, ZAK(MLTK), MAP3K1, LIMK1, and RSK2. It binds to the cysteine located in vicinity of active site. In some cases, SM1-71 might bind to Cys located at allosteric places. SM1-71 potently inhibits growth of multiple cancer cell lines.
cell penetrant and potent multi-targeted kinase inhibitor that engages kinases through both reversible and irreversible binding

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000096687
0000096688
0000096685
0000096684
0000092125

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Li Tan et al.
Bioorganic & medicinal chemistry, 25(3), 838-846 (2016-12-25)
TAK1 (transforming growth factor-β-activated kinase 1) is an essential intracellular mediator of cytokine and growth factor signaling and a potential therapeutic target for the treatment of immune diseases and cancer. Herein we report development of a series of 2,4-disubstituted pyrimidine
Suman Rao et al.
The Journal of biological chemistry, 294(21), 8664-8673 (2019-03-13)
Most cancer cells are dependent on a network of deregulated signaling pathways for survival and are insensitive, or rapidly evolve resistance, to selective inhibitors aimed at a single target. For these reasons, drugs that target more than one protein (polypharmacology)
Suman Rao et al.
Cell chemical biology, 26(6), 818-829 (2019-04-16)
Covalent kinase inhibitors, which typically target cysteine residues, represent an important class of clinically relevant compounds. Approximately 215 kinases are known to have potentially targetable cysteines distributed across 18 spatially distinct locations proximal to the ATP-binding pocket. However, only 40

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