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D1944

Sigma-Aldrich

D4476

≥98% (HPLC), solid

Synonym(s):

4-(4-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-5-pyridin-2-yl-1H-imidazol-2-yl)benzamide

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About This Item

Empirical Formula (Hill Notation):
C23H18N4O3
CAS Number:
301836-43-1
Molecular Weight:
398.41
UNSPSC Code:
12352200
PubChem Substance ID:
329798715
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

light yellow

solubility

DMSO: ~20 mg/mL
H2O: insoluble

originator

GlaxoSmithKline

storage temp.

2-8°C

SMILES string

NC(=O)c1ccc(cc1)-c2nc(-c3ccccn3)c([nH]2)-c4ccc5OCCOc5c4

InChI

1S/C23H18N4O3/c24-22(28)14-4-6-15(7-5-14)23-26-20(21(27-23)17-3-1-2-10-25-17)16-8-9-18-19(13-16)30-12-11-29-18/h1-10,13H,11-12H2,(H2,24,28)(H,26,27)

InChI key

DPDZHVCKYBCJHW-UHFFFAOYSA-N

Application

D4476 has been used as a casein kinase I inhibitor (CKI) in various experiments.

Biochem/physiol Actions

D4476 may prevent or enhance apoptosis. It triggers tumor suppressor p53 and impairs transcription factor E2F-1.
D4476 is a potent, selective ATP-competitive inhibitor of CK1 (casein kinase 1).

Features and Benefits

This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Graham Rena et al.
EMBO reports, 5(1), 60-65 (2004-01-08)
The protein kinase CK1 phosphorylates serine residues that are located close to another phosphoserine in the consensus pSer-Xaa-Xaa-Ser. This specificity generates regions in its target proteins containing two or more neighbouring phosphoserine residues, termed here multisite phosphorylation domains (MPDs). In
CK1alpha plays a central role in mediating MDM2 control of p53 and E2F-1 protein stability
Huart AS, et al.
The Journal of biological chemistry, 284(47), 32384-32394 (2009)
Phosphorylation of serine 235 of the hepatitis C virus non-structural protein NS5A by multiple kinases
Lee KY, et al.
PLoS ONE, 11(11), e0166763-e0166763 (2016)
Serine 235 is the primary NS5A hyperphosphorylation site responsible for hepatitis C virus replication
Hsu SC, et al.
Journal of Virology, 91(14), e00194-e00117 (2017)
Yuliya V Katlinskaya et al.
Molecular and cellular biology, 36(7), 1124-1135 (2016-01-27)
Wnt pathway-driven proliferation and renewal of the intestinal epithelium must be tightly controlled to prevent development of cancer and barrier dysfunction. Although type I interferons (IFN) produced in the gut under the influence of microbiota are known for their antiproliferative
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