ChemicalBook > CAS DataBase List > AG 490

AG 490

Product Name: AG 490
CAS No.: 133550-30-8
Chemical Name: AG 490
Synonyms: AG 49;CS-316;AG 490;Zinc02557947;AG490,AG-490;zinc0255794);AG 490, >=98%;TYRPHOSTIN B42;TYRPHOSTIN AG 490;TYROPHOSTIN AG490
CBNumber: CB4779212
Molecular Formula: C17H14N2O3
Formula Weight: 294.3
MOL File: 133550-30-8.mol

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AG 490 Property

Melting point:: 215°C(lit.)
Boiling point:: 615.2±55.0 °C(Predicted)
Density: 1.337
storage temp.: -20°C
solubility: ethanol: 5 mg/mL
form: solid
pka: 8.75±0.10(Predicted)
color: yellow
biological source: synthetic (organic)
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO, DMF, or ethanol may be stored at -20°C for up to 1 month.
InChI: InChI=1S/C17H14N2O3/c18-10-14(8-13-6-7-15(20)16(21)9-13)17(22)19-11-12-4-2-1-3-5-12/h1-9,20-21H,11H2,(H,19,22)/b14-8+
InChIKey: TUCIOBMMDDOEMM-ZSOIEALJSA-N
SMILES: C(NCC1=CC=CC=C1)(=O)/C(/C#N)=C/C1=CC=C(O)C(O)=C1

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Safety

Hazard Codes: Xi,N,T
Risk Statements: 36/37/38-50-25
Safety Statements: 26-36-61-45
RIDADR: UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., HI: all
WGK Germany: 1
RTECS: UC6316197
HazardClass: 6.1
PackingGroup: III
HS Code: 29269090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H400Very toxic to aquatic life

Precautionary statements

P273Avoid release to the environment.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: T3434
Product name: Tyrphostin AG 490
Purity: solid
Packaging: 5mg
Price: $104
Updated: 2025/07/31

Sigma-Aldrich

Product number: 658401
Product name: AG 490
Packaging: 5mg
Price: $73.1
Updated: 2025/07/31

TCI Chemical

Product number: T2962
Product name: Tyrphostin AG 490
Purity: >98.0%(HPLC)(T)
Packaging: 20mg
Price: $38
Updated: 2025/07/31

TCI Chemical

Product number: T2962
Product name: Tyrphostin AG 490
Purity: >98.0%(HPLC)(T)
Packaging: 100mg
Price: $114
Updated: 2024/03/01

Cayman Chemical

Product number: 10010311
Product name: AG 490
Purity: ≥98%
Packaging: 5mg
Price: $32
Updated: 2024/03/01

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AG 490 Chemical Properties,Usage,Production

Description

AG-490 (133550-30-8) is a potent inhibitor of the JAK2 tyrosine kinase. In acute lymphoblastic leukemia (ALL) cells, which abundantly express JAK-2, AG-490 dose-dependently blocked cell growth, induced apoptosis and inhibited DNA synthesis. Blocks the growth of all pre-B ALL cells with no effect on normal B or T cells. Does not significantly inhibit other kinases such as Lck, Lyn, Btk, Syk and Src. Reduces liver injury in LPS-induced shock.3 AG-490 is a useful tool for exploring the role of JAK2/STAT3 pathway in physiologic processes.4

Uses

AG 490 is a potent epidermal growth factor receptor kinase autophosphorylation inhibitor with an IC50 of 100 nM and 56.8 μM for EGFR and JAK, respectively.

Uses

Tyrphostin AG has been used to block IL-6 cytokine signaling to study its effects on glial cell reactivity⁵. AG 490 has also been used as a JAK2 inhibitor in human umbilical vein endothelial cells⁶.

Definition

ChEBI: Tyrphostin B42 is a monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2E)-2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enoic acid with the amino group of benzylamine. It has a role as an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor, an antioxidant, a STAT3 inhibitor, an anti-inflammatory agent, an apoptosis inducer and a geroprotector. It is an enamide, a monocarboxylic acid amide, a nitrile, a member of catechols and a secondary carboxamide.

Biological Activity

Selective inhibitor of EGF receptor tyrosine kinase (IC 50 values are 2 and 13.5 μ M for EGFR and ErbB2 respectively). Inhibitor of JAK2, JAK3/STAT, JAK3/AP-1 and JAK3/MAPK pathways and potently inhibits cytokine-independent cell growth in vitro and tumor cell invasion in vivo .

Biochem/physiol Actions

Jak-2 protein tyrosine kinase (PTK) inhibitor. Inhibits interleukin 2 (IL-2) driven mitogenesis and triggers apoptosis of tumor cells in Sezary syndrome, a leukemic variant of cutaneous T cell lymphoma.

Synthesis

10412-93-8

139-85-5

133550-30-8

Example 1; General method of compound synthesis; (E)-N-benzyl-2-cyano-3-(3,4-dihydroxyphenyl)acrylamide was prepared by the following general procedure. Benzylamine (3.0 g, 28 mmol) and ethyl cyanoacetate (4.7 g, 42 mmol) were dissolved in acetonitrile (20 mL), stirred and refluxed for 4 hours. The benzylamine in this general method can be replaced by other R3 substituents. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give an oil, which solidified to the intermediate N-benzyl-2-cyanoacetamide upon standing. An off-white powder of 3.28 g (68% yield) was obtained by ethyl acetate precipitation. Subsequently, N-benzyl-2-cyanoacetamide (1.3 g, 7.5 mmol), 3,4-dihydroxybenzaldehyde (1.1 g, 8.2 mmol) and a catalytic amount of piperidine (5 drops) were mixed and stirred under reflux conditions for 3 hours. The reaction mixture was purified by fast column chromatography (ethyl acetate as eluent) and then recrystallized twice by water/ethanol solvent mixture to give 0.8 g (36% yield) of the target product in white powder form.

storage

Room temperature

References

[1] L H WANG. JAK3, STAT, and MAPK signaling pathways as novel molecular targets for the tyrphostin AG-490 regulation of IL-2-mediated T cell response.[J]. Journal of immunology, 1999, 162 7: 3897-3904.
[2] NAFTALY MEYDAN. Inhibition of acute lymphoblastic leukaemia by a Jak-2 inhibitor[J]. Nature, 1996, 379 6566: 645-648. DOI:10.1038/379645a0
[3] VALERIYA GYURKOVSKA Nina I. Tyrosine kinase inhibitor tyrphostin AG490 reduces liver injury in LPS-induced shock[J]. European journal of pharmacology, 2015, 751: Pages 118-126. DOI:10.1016/j.ejphar.2015.01.045
[4] LAN WU . ROS generated during early reperfusion contribute to intermittent hypobaric hypoxia-afforded cardioprotection against postischemia-induced Ca2 + overload and contractile dysfunction via the JAK2/STAT3 pathway[J]. Journal of molecular and cellular cardiology, 2015, 81: Pages 150-161. DOI:10.1016/j.yjmcc.2015.02.015

AG 490 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from AG 490 manufacturers

Career Henan Chemical Co

Product: AG 490 133550-30-8
Price: US $2.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 100kg
Release date: 2018-12-24

133550-30-8, AG 490Related Search:

TYRPHOSTIN B48 TYRPHOSTIN A1 TYRPHOSTIN A9 TYRPHOSTIN AG 528 Stattic WORTMANNIN 1,9-Pyrazoloanthrone PD 98059 SB 203580 LY 294002 Hydrochloride TYRPHOSTIN AG 835 TYRPHOSTIN AG 490, 99+%,AG 490,TYROPHOSTIN AG490,TYRPHOSTIN AG 490 Tyrphostin AG 490 (N-benzyl-3,4-dihydroxy-benzylidenecyanoacetamide) TYRPHOSTIN B44 AG 490 AURORA 12314 OTAVA-BB BB7015051722 OTAVA-BB BB7015051721

AG 490;TYRPHOSTIN AG 490;AG490;ZINC02557947;AG-490 (TYRPHOSTIN B42)

CS-316

AG 490 - CAS 133550-30-8 - Calbiochem

2-CYANO-3-[3,4-DIHYDROXYPHENYL]-N-[PHENYLMETHYL]-2-PROPENAMIDE

N-BENZYL-3,4-DIHYDROXY-ALPHA-CYANOCINNAMIDE

N-BENZYL-3,4-DIHYDROXY-BENZYLIDENECYANOACETAMIDE

TYROPHOSTIN AG490

TYRPHOSTIN AG 490

TYRPHOSTIN B42

2-cyano-3-(3,4-dihydroxyphenyl)-n-(benzyl)-2-propenamide

bis-tyrphostin B42

AG 490 (Tyrphostin AG 490)

N-Benzyl-2-cyano-3-(3,4-dihydroxy-phenyl)-acrylamide

(E)-N-benzyl-2-cyano-3-(3,4-dihydroxyphenyl)acrylamide

(2E)-2-Cyano-3-(3,4-dihydroxyphenyl)-N-(phenylmethyl)-2-propenamide

AG 490(Tyrphostin AG 490,Tyrphostin B42)

2-PropenaMide, 2-cyano-3-(3,4-dihydroxyphenyl)-N-(phenylMethyl)-, (2E)-

(E)-2-CYANO-3-(3,4-DIHYDROPHENYL)-N-(PHENYLMETHYL)-2-PROPENAMIDE

A-CYANO-(3,4-DIHYDROXY)-N-BENZYLCINNAMAMIDE

A-CYANO-(3,4-DIHYDROXY)-N-BENZYLCINNAMIDE

AG 490

ALPHA-CYANO-(3,4-DIHYDROXY)-N-BENZYLCINNAMIDE

Zinc02557947

AG-490 (Tyrphostin B42)

(2E)-2-Cyano-3-(3,4-dihydroxyphenyl)-N-(phenylmethyl)-2-propenamide AG-490(Tyrphostin B42)

Tyrphostin AG 490 AG 490

AG 490, >=98%

(E)-N-benzyl-2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enamide

AG490,AG-490

AG-490, 99%, an inhibitor of EGFR

0 Tyrphostin AG 490

AG490(Tyrphostin )

zinc0255794)

TIANFU-CHEM AG 490

Tyrphostin B42 (AG-490)

Tyrphostin AG490 AG-490 JAK-2 specific inhibitor

Epidermal growth factor receptor,Inhibitor,Tyrphostin AG490,Tyrphostin B-42,ErbB-1,STAT,Janus kinase,AG490,Autophagy,Tyrphostin B 42,EGFR,HER1,inhibit,Tyrphostin AG-490,JAK

AG 49

AG 490, JAK2/3 inhibitor

AG490, 10 mM in DMSO

133550-30-8

Cell Signaling and Neuroscience

Cell Biology

BioChemical

Non-Receptor Tyrosine Kinase Inhibitors

Kinase/Phosphatase Biology

Janus Kinase (JAK)

Intracellular Signaling

Inhibitors

Inhibitor

Protein Kinase