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]- Structure](CAS/GIF/919486-40-1.gif)
- 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
- Molecular Weight:
- 397.86
- MDL Number:
- MFCD24038757
- MOL File:
- 919486-40-1.mol
- MSDS File:
- SDS
5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]- Properties
| 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 |
| FDA UNII | 2H31HOT08T |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302 |
| Precautionary statements | P280-P305+P351+P338 |
5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]- price More Price(23)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | SML1906 | AS1517499 ≥98% (HPLC) | 919486-40-1 | 5MG | $128 | 2023-06-20 | Buy |
| Sigma-Aldrich | SML1906 | AS1517499 ≥98% (HPLC) | 919486-40-1 | 25MG | $517 | 2023-06-20 | Buy |
| Cayman Chemical | 29071 | AS1517499 | 919486-40-1 | 5mg | $116 | 2024-03-01 | Buy |
| Cayman Chemical | 29071 | AS1517499 | 919486-40-1 | 25mg | $381 | 2024-03-01 | Buy |
| Cayman Chemical | 29071 | AS1517499 | 919486-40-1 | 1mg | $32 | 2024-03-01 | Buy |
5-PyriMidinecarboxaMide, 2-[[2-(3-chloro-4-hydroxyphenyl)ethyl]aMino]-4-[(phenylMethyl)aMino]- Chemical Properties,Uses,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
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 33024 | 60 |
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 32159 | 58 |
| InvivoChem | +1-708-310-1919 +1-13798911105 | sales@invivochem.cn | United States | 6391 | 58 |
| Nantong HI-FUTURE Biology Co., Ltd. | +undefined18051384581 | sales@chemhifuture.com | China | 3135 | 58 |
| TargetMol Chemicals Inc. | support@targetmol.com | United States | 38630 | 58 | |
| LEAPCHEM CO., LTD. | +86-852-30606658 | market18@leapchem.com | China | 43340 | 58 |
| Aladdin Scientific | tp@aladdinsci.com | United States | 57505 | 58 | |
| Amadis Chemical Company Limited | 571-89925085 | sales@amadischem.com | China | 131957 | 58 |
| BOC Sciences | 1-631-485-4226; 16314854226 | info@bocsci.com | United States | 12952 | 65 |
| Wuhan TCASChem Technology Co., Ltd. | 027-86697669 13986148687 | sales@tcaschem.com | China | 4220 | 55 |
