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301836-43-1

4-(4-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-5-pyridin-2-yl-1H-imidazol-2-yl)benzamide, also known as D4476, is a cell-permeant inhibitor of casein kinase 1 (CK1) with an IC50 value of 78 nM. It is a potent and selective inhibitor that blocks CK1-mediated phosphorylation of various proteins, such as FOXO1a, RhoB, and p53. D4476 also exhibits inhibitory effects on other kinases like PKD1 and p38α MAPK, but to a lesser extent. As an inhibitor of ALK5, it prevents Smad3 activation and suppresses TGF-β1-induced gene expression without cytotoxicity in A498 cells.

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  • 301836-43-1 Structure

  • Basic information

    1. Product Name: 4-(4-(2,3-DIHYDROBENZO[1,4]DIOXIN-6-YL)-5-PYRIDIN-2-YL-1H-IMIDAZOL-2-YL)BENZAMIDE
    2. Synonyms: 4-(4-(2,3-DIHYDROBENZO[1,4]DIOXIN-6-YL)-5-PYRIDIN-2-YL-1H-IMIDAZOL-2-YL)BENZAMIDE;D4476;4-[4-(2,3-Dihydro-1,4-benzodioxin-6-yl)-5-(2-pyridinyl)-1H-imidazol-2-yl]benzamide;Casein Kinase I Inhibitor;4-[4-(2,3-Dihydro-1,4-benzodioxin-6-yl)-5-(2-pyridinyl)-1H-imidazol-2-yl]benzamide D4476;Casein Kinase I Inhibitor, D4476;Benzamide,4-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-(2-pyridinyl)-1H-imidazol-2-yl]-;4-(4-(2,3-DIHYDROBENZO[B][1,4]DIOXIN-6-YL)-5-(PYRIDIN-2-YL)-1H-IMIDAZOL-2-YL)BENZAMIDE
    3. CAS NO:301836-43-1
    4. Molecular Formula: C23H18N4O3
    5. Molecular Weight: 398.41402
    6. EINECS: N/A
    7. Product Categories: Signalling;Inhibitors
    8. Mol File: 301836-43-1.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 675.0±55.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: light yellow/
    5. Density: 1.338±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: DMSO: ~20mg/mL
    9. PKA: 10.16±0.10(Predicted)
    10. CAS DataBase Reference: 4-(4-(2,3-DIHYDROBENZO[1,4]DIOXIN-6-YL)-5-PYRIDIN-2-YL-1H-IMIDAZOL-2-YL)BENZAMIDE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 4-(4-(2,3-DIHYDROBENZO[1,4]DIOXIN-6-YL)-5-PYRIDIN-2-YL-1H-IMIDAZOL-2-YL)BENZAMIDE(301836-43-1)
    12. EPA Substance Registry System: 4-(4-(2,3-DIHYDROBENZO[1,4]DIOXIN-6-YL)-5-PYRIDIN-2-YL-1H-IMIDAZOL-2-YL)BENZAMIDE(301836-43-1)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 301836-43-1(Hazardous Substances Data)

301836-43-1 Usage

Uses

Used in Pharmaceutical Industry:
4-(4-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-5-pyridin-2-yl-1H-imidazol-2-yl)benzamide is used as a casein kinase I inhibitor (CKI) for various experimental purposes. It is particularly valuable in the development of novel therapeutic strategies targeting CK1, which plays a crucial role in various cellular processes and is implicated in several diseases.
Used in Research Applications:
In the field of research, D4476 is used as a potent CK1 inhibitor to study the role of CK1 in cellular signaling pathways and its potential as a therapeutic target for various diseases. Its ability to inhibit CK1 with high selectivity makes it a valuable tool for understanding the molecular mechanisms underlying CK1-mediated processes.
Used in Drug Development:
4-(4-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-5-pyridin-2-yl-1H-imidazol-2-yl)benzamide is used as a lead compound in the development of new drugs targeting CK1. Its potent inhibition of CK1 and selectivity over other kinases make it an attractive starting point for designing more effective and specific CK1 inhibitors for therapeutic use.
Used in Cancer Research:
In cancer research, D4476 is employed as an inhibitor of CK1, which is involved in the regulation of cell cycle progression and apoptosis. By inhibiting CK1, D4476 may help to understand the role of this kinase in cancer development and progression, and potentially lead to the development of new anticancer drugs targeting CK1.

Biological Activity

Selective inhibitor of casein kinase 1 (CK1) and TGF- β type-I receptor (ALK5) that displays > 20-fold selectivity over SAPK2/p38 and a much greater selectivity over all other protein kinases tested. Suppresses site-specific phosphorylation and nuclear exclusion of FOXO1a.

Biochem/physiol Actions

D4476 may prevent or enhance apoptosis. It triggers tumor suppressor p53 and impairs transcription factor E2F-1.

references

1. g. rena, j. bain, m. elliott and p. cohen, embo rep 2004, 5, 60-65. 2. v. tillement, i. lajoie-mazenc, a. casanova, c. froment, m. penary, d. tovar, r. marquez, b. monsarrat, g. favre and a. pradines, exp cell res 2008, 314, 2811-2821. 3. a. s. huart, n. j. maclaine, d. w. meek and t. r. hupp, j biol chem 2009, 284, 32384-32394.

Check Digit Verification of cas no

The CAS Registry Mumber 301836-43-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,0,1,8,3 and 6 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 301836-43:
(8*3)+(7*0)+(6*1)+(5*8)+(4*3)+(3*6)+(2*4)+(1*3)=111
111 % 10 = 1
So 301836-43-1 is a valid CAS Registry Number.

301836-43-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
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  • Sigma

  • (D1944)  D4476  ≥98% (HPLC), solid

  • 301836-43-1

  • D1944-1MG

  • 1,842.75CNY

  • Detail

  • Sigma

  • (D1944)  D4476  ≥98% (HPLC), solid

  • 301836-43-1

  • D1944-5MG

  • 7,318.35CNY

  • Detail

301836-43-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-pyridin-2-yl-1H-imidazol-2-yl]benzamide

1.2 Other means of identification

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

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:301836-43-1 SDS

301836-43-1Downstream Products

301836-43-1Relevant articles and documents

Triarylimidazoles

-

, (2008/06/13)

Compounds of formula (I) or a pharmaceutically acceptable salt thereof: wherein R1, R2and R3are various substituent groups; and one of X1and X2is N or CR′, and the other is NR′ or CHR′ wherein R′ is hydrogen, OH, C1-6alkyl, or C3-7cycloalkyl; or when one of X1and X2is N or CR′ then the other may be S or O; and their use as pharmaceuticals.

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