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SML2609

JH-I-25

≥98% (HPLC)

Synonym(s):

N-[2-Methoxy-4-(4-morpholinyl)phenyl]-6-(1H-pyrazol-3-yl)-2-pyridinecarboxamide

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About This Item

Empirical Formula (Hill Notation):
C20H21N5O3
CAS Number:
1042673-20-0
Molecular Weight:
379.41
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
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assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

O=C(NC1=C(C=C(C=C1)N2CCOCC2)OC)C3=NC(C4=NNC=C4)=CC=C3

InChI

1S/C20H21N5O3/c1-27-19-13-14(25-9-11-28-12-10-25)5-6-17(19)23-20(26)18-4-2-3-15(22-18)16-7-8-21-24-16/h2-8,13H,9-12H2,1H3,(H,21,24)(H,23,26)

InChI key

RAFFLDOJXQAJPF-UHFFFAOYSA-N

Biochem/physiol Actions

JH-I-25 is a potent and selective type I inhibitor of IRAK1 and IRAK4 (interleukin-1 receptor–associated kinase 1 and 4). JH-I-25 binds preferentially to the unphosphorylated the ATP-site of the kinase in its active, DFG-in, state.
potent and selective type I inhibitor of IRAK1 and IRAK4

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000075522
0000075521
0000072258

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Li Wang et al.
Proceedings of the National Academy of Sciences of the United States of America, 114(51), 13507-13512 (2017-12-07)
Interleukin 1 (IL-1) receptor-associated kinases (IRAKs) are serine/threonine kinases that play critical roles in initiating innate immune responses against foreign pathogens and other types of dangers through their role in Toll-like receptor (TLR) and interleukin 1 receptor (IL-1R) mediated signaling
George M Buckley et al.
Bioorganic & medicinal chemistry letters, 18(11), 3211-3214 (2008-05-14)
The synthesis and profile of a series of amides are described. Some of these compounds were potent IRAK-4 inhibitors and two examples were evaluated in vivo.
Li Wang et al.
The Journal of biological chemistry, 294(12), 4511-4519 (2019-01-27)
Interleukin-1 receptor-associated kinase 4 (IRAK4) is a key player in innate immune and inflammatory responses, performing a critical role in signal transduction downstream of Toll-like receptors and interleukin-1 (IL-1) receptors. Upon ligand binding and via its N-terminal death domain, IRAK4