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Merck
CN

SML2703

BAY-293

≥98% (HPLC)

Synonym(s):

6,7-Dimethoxy-2-methyl-N-[(R)-1-(4-{2-[(methylamino)methyl]phenyl}thien-2-yl)ethyl]quinazolin-4-amine, BAY 293, BAY293

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About This Item

Empirical Formula (Hill Notation):
C25H28N4O2S
CAS Number:
2244904-70-7
Molecular Weight:
448.58
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

BAY-293, ≥98% (HPLC)

form

powder

InChI

1S/C25H28N4O2S/c1-15(24-10-18(14-32-24)19-9-7-6-8-17(19)13-26-3)27-25-20-11-22(30-4)23(31-5)12-21(20)28-16(2)29-25/h6-12,14-15,26H,13H2,1-5H3,(H,27,28,29)/t15-/m1/s1

InChI key

WEGLOYDTDILXDA-OAHLLOKOSA-N

SMILES string

C[C@H](C1=CC(C2=CC=CC=C2CNC)=CS1)NC3=C4C=C(C(OC)=CC4=NC(C)=N3)OC

assay

≥98% (HPLC)

optical activity

[α]/D -85.0 to -103.0°, c = 1.0 in DMSO

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

BAY-293 selectively inhibits SOS1-mediated KRAS activation (IC50 = 52 nM; 50 nM wt or G12C hKRAS & 10 nM SOS1cat) via direct SOS1 binding, blocking SOS1-KRAS interaction (IC50 = 21 nM; 10 nM hSOS1cat & 5 nM hKRAS G12C) without affecting (IC50 >20 μM) CRAF RBD-KRAS interaction, KRAS G12C activation by SOS2, Cdc42 activation by DBS, or EGFR kinase activity. BAY-293 downregulates cellular active RAS (IC50 = 200 nM/Calu-1, 410 nM/HeLa) and downstream ERK phosphorylation (K-562, 150 nM/Calu-1) with good target selectivity as assessed over 358 kinases (<37% inhibition at 1 μM) and a panel of 77 GPCRs, transporters, nuclear receptors and enzymes.
Selective inhibitor against SOS1-mediated KRAS activation without affecting CRAF RBD-KRAS interaction or KRAS G12C activation by SOS2.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000126803
0000126804
0000118798

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Roman C Hillig et al.
Proceedings of the National Academy of Sciences of the United States of America, 116(7), 2551-2560 (2019-01-27)
Since the late 1980s, mutations in the RAS genes have been recognized as major oncogenes with a high occurrence rate in human cancers. Such mutations reduce the ability of the small GTPase RAS to hydrolyze GTP, keeping this molecular switch

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