134036-52-5

Basic information

• Product Name: AG 490
• Synonyms: (E)-2-CYANO-3-(3,4-DIHYDROPHENYL)-N-(PHENYLMETHYL)-2-PROPENAMIDE;ALPHA-CYANO-(3,4-DIHYDROXY)-N-BENZYLCINNAMIDE;AG 490;A-CYANO-(3,4-DIHYDROXY)-N-BENZYLCINNAMAMIDE;A-CYANO-(3,4-DIHYDROXY)-N-BENZYLCINNAMIDE;2-CYANO-3-[3,4-DIHYDROXYPHENYL]-N-[PHENYLMETHYL]-2-PROPENAMIDE;N-BENZYL-3,4-DIHYDROXY-ALPHA-CYANOCINNAMIDE;N-BENZYL-3,4-DIHYDROXY-BENZYLIDENECYANOACETAMIDE
• CAS NO: 134036-52-5
• Molecular Formula: C17H14N2O3
• Molecular Weight: 294.3
• EINECS: 604-604-1
• Product Categories: All Inhibitors;Inhibitors;Tyrosine Kinase Inhibitors;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitor
• Mol File: 134036-52-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 215
• Boiling Point: 615.2 °C at 760 mmHg
• Flash Point: 325.9 °C
• Appearance: yellow/solid
• Density: 1.337 g/cm³
• Vapor Pressure: 9.95E-16mmHg at 25°C
• Refractive Index: 1.678
• Storage Temp.: −20°C
• Solubility: ethanol: 5 mg/mL
• PKA: 8.82±0.35(Predicted)
• CAS DataBase Reference: AG 490(CAS DataBase Reference)
• NIST Chemistry Reference: AG 490(134036-52-5)
• EPA Substance Registry System: AG 490(134036-52-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-50-25
• Safety Statements: 26-36-61-45
• WGK Germany: 1
• Hazardous Substances Data: 134036-52-5(Hazardous Substances Data)

Usage

Description

AG 490, also known as a potent and specific inhibitor of the Jak-2 tyrosine kinase, is a chemical compound with pale yellow-green crystal properties. It is particularly effective in inhibiting the JAK-2 enzyme, which is abundantly expressed in acute lymphoblastic leukemia (ALL) cells. AG 490 demonstrates cell permeability and is active in vivo, making it a valuable compound for various applications.

Uses

Used in Pharmaceutical Industry:
AG 490 is used as an inhibitor for the JAK-2 tyrosine kinase, specifically targeting and inhibiting the enzyme in acute lymphoblastic leukemia (ALL) cells. This application is crucial for blocking cell growth, inhibiting DNA synthesis, and inducing apoptosis in these cells.
AG 490 is also used as a research tool in the study of acute lymphoblastic leukemia, where it has been reported to inhibit JAK2 from B cell precursors, providing valuable insights into the disease's mechanisms and potential treatment strategies.
Additionally, AG 490 is used as a compound for investigating the effects of JAK-2 inhibition on various cellular processes, as it does not significantly inhibit other kinases such as Lck, Lyn, Btk, Syk, and Src. This selective inhibition allows for a more focused study of the JAK-2 pathway and its role in cellular functions.

Upstream product

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Relevant articles and documents

COMPOUNDS FOR TREATMENT OF CELL PROLIFERATIVE DISEASES

The present invention concerns compounds and their use to treat cell proliferative diseases such as cancer. Compounds of the present invention display significant potency as kinase inhibitors, cause the downregulation of c-myc, and inhibit the growth and survival of cancerous cell lines.

Structure-activity relationship of N-(phenylalkyl)cinnamides as novel NR2B subtype-selective NMDA receptor antagonists

A novel series of N-(phenylalkyl)cinnamides related to N-(4- phenylbutyl)-3,4-dihydroxy-β-cyanocinnamide (6, an EGFR-K inhibitor with high antiproliferative activity) was synthesized and tested for antagonism at N-methyl-D-aspartate (NMDA) receptor subtypes. Potency and subunit selectivity were assayed by electrical recordings in Xenopus oocytes expressing three binary combinations of cloned rat NMDA receptor subunits: NR1A expressed in combination with either NR2A, NR2B, or NR2C. The N- (phenylalkyl)cinnamides are selective antagonists of NR1(A)/2B receptors. Assayed under steady-state conditions, N-(4-phenylbutyl)-4-hydroxycinnamide (16) has an IC50 value of 77 nM and > 1000-fold selectivity with respect to NR1(A)/2A and NR1(A)/2C receptors. Potency at α1 adrenergic receptors is low for the four cinnamides tested. Inhibition of NR1(A)/2B receptors does not correlate with EGFR and ErbB2/neu tyrosine kinase inhibitor activity. The N-(phenylalkyl)cinnamide series we describe provides a novel and structurally diverse framework for designing new NR2B-selective NMDA antagonists as potential CNS therapeutics.