ChemicalBook > CAS DataBase List > 5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]-

5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]-

Product Name
5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]-
CAS No.
919486-40-1
Chemical Name
5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]-
Synonyms
CS-2440;AS 1517499;AS-1517499;AS 1517499;AS1517499, 10 mM in DMSO;AS-1517499; AS1517499; AS 1517499;919486-40-1;STAT,AS-1517499,inhibit,AS 1517499,AS1517499,Inhibitor;4-(Benzylamino)-2-((3-chloro-4-hydroxyphenethyl)amino)pyrimidine-5-carboxamide;5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]-
CBNumber
CB82624615
Molecular Formula
C20H20ClN5O2
Formula Weight
397.86
MOL File
919486-40-1.mol
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5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]- Property

storage temp. 
2-8°C
solubility 
DMF: 25mg/mL; DMF:PBS (pH 7.2) (1:6): 0.14mg/mL; DMSO: 15mg/mL; Ethanol: 5mg/mL
form 
powder
color 
white to beige
InChI
InChI=1S/C20H20ClN5O2/c21-16-10-13(6-7-17(16)27)8-9-23-20-25-12-15(18(22)28)19(26-20)24-11-14-4-2-1-3-5-14/h1-7,10,12,27H,8-9,11H2,(H2,22,28)(H2,23,24,25,26)
InChIKey
OZRMEKAUZBKTTC-UHFFFAOYSA-N
SMILES
C1(NCCC2=CC=C(O)C(Cl)=C2)=NC=C(C(N)=O)C(NCC2=CC=CC=C2)=N1
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML1906
Product name
AS1517499
Purity
≥98% (HPLC)
Packaging
5MG
Price
$142
Updated
2025/07/31
Sigma-Aldrich
Product number
SML1906
Product name
AS1517499
Purity
≥98% (HPLC)
Packaging
25MG
Price
$545
Updated
2025/07/31
Cayman Chemical
Product number
29071
Product name
AS1517499
Packaging
5mg
Price
$116
Updated
2024/03/01
Cayman Chemical
Product number
29071
Product name
AS1517499
Packaging
25mg
Price
$381
Updated
2024/03/01
Cayman Chemical
Product number
29071
Product name
AS1517499
Packaging
1mg
Price
$32
Updated
2024/03/01
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5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]- Chemical Properties,Usage,Production

Description

AS1517499 is a STAT6 inhibitor (IC50 = 21 nM in a reporter assay). It inhibits IL-4-induced Th2 differentiation (IC50 = 2.3 nM), but not IL-12-induced Th1 differentiation, of mouse spleen T cells. AS1517499 (10 mg/kg) inhibits bronchial smooth muscle hyperresponsiveness and IL-13 production in ovalbumin-sensitized mice when administered one hour prior to antigen exposure. It inhibits STAT6 phosphorylation and thyroid epithelial cell (TEC) hyperplasia and decreases serum levels of 3,3'',5-triiodo-L-thyronine (T3; ) and thyroxine (T4) in a mouse model of Graves'' disease when administered at a dose of 10 mg/kg per day. AS1517499 (20 mg/kg twice weekly) also inhibits tumor growth and liver metastasis in a murine orthotopic 4T1 mammary carcinoma model.

Uses

AS1517499 is a potent and brain-permeable STAT6 phosphorylation inhibitor with an IC50 of 21 nM.

Biochem/physiol Actions

AS1517499 moderately inhibits the expression of RhoA (ras homolog family member A). Overexpression of RhoA protein is associated with allergic bronchial asthma.

in vivo

In BALB/c mice that are actively sensitized and repeatedly challenged with ovalbumin antigen, an increased IL-13 level in bronchoalveolar lavage fluids and a phosphorylation of STAT6 in bronchial tissues are observed after the last antigen challenge. These mice have an augmented BSM contractility to acetylcholine together with an up-regulation of RhoA in bronchial tissues. Intraperitoneal injections of AS1517499 (10 mg/kg) 1 hour before each ovalbumin exposure inhibits both the antigen-induced up-regulation of RhoA and BSM hyperresponsiveness, almost completely[2].

IC 50

STAT6: 21 nM (IC50)

storage

Store at -20°C

References

[1] Nagashima S, et al. Synthesis and evaluation of 2-{[2-(4-hydroxyphenyl)-ethyl]amino}pyrimidine-5-carboxamide derivatives as novel STAT6 inhibitors. Bioorg Med Chem. 2007 Jan 15;15(2):1044-55. DOI:10.1016/j.bmc.2006.10.015
[2] Chiba Y, et al. A novel STAT6 inhibitor AS1517499 ameliorates antigen-induced bronchial hypercontractility in mice. Am J Respir Cell Mol Biol. 2009 Nov;41(5):516-24. DOI:10.1165/rcmb.2008-0163OC

5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]- Preparation Products And Raw materials

Raw materials

Preparation Products

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5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]- Suppliers

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919486-40-1, 5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]-Related Search:


  • 5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]-
  • AS 1517499
  • 4-(Benzylamino)-2-((3-chloro-4-hydroxyphenethyl)amino)pyrimidine-5-carboxamide
  • AS-1517499;AS 1517499
  • AS-1517499; AS1517499; AS 1517499;919486-40-1
  • CS-2440
  • STAT,AS-1517499,inhibit,AS 1517499,AS1517499,Inhibitor
  • AS1517499, 10 mM in DMSO
  • 919486-40-1