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N-{3-[(5-Chloro-2-{[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)oxy]phenyl}acrylamide

N-{3-[(5-Chloro-2-{[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)oxy]phenyl}acrylamide

CAS: 1213269-23-8

Molecular Formula: C25H27ClN6O3

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N-{3-[(5-Chloro-2-{[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)oxy]phenyl}acrylamide - Names and Identifiers

Name N-{3-[(5-Chloro-2-{[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)oxy]phenyl}acrylamide
Synonyms CS-166
WZ4002
WZ4002(HBr)
N-(3-(5-chloro-2-(2-methoxy-4-(4-methylpiperazin-1-yl)phenylamino)pyrimidin-4-yloxy)phenyl)acrylamide
N-{3-[(5-Chloro-2-{[2-Methoxy-4-(4-Methyl-1-piperazinyl)phenyl]aMino}-4-pyriMidinyl)oxy]phenyl}acrylaMide
N-{3-[(5-Chloro-2-{[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)oxy]phenyl}acrylamide
N-[3-[[5-Chloro-2-[[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]amino]-4-pyrimidinyl]oxy]phenyl]-2-propenamide
N-[3-[[5-Chloro-2-[[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]amino]-4-pyrimidinyl]oxy]phenyl]-2-propenamide WZ 4002
WZ 4002 N-[3-[[5-Chloro-2-[[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]amino]-4-pyrimidinyl]oxy]phenyl]-2-propenamide
CAS 1213269-23-8
EINECS 206-141-6
InChI InChI=1S/C25H27ClN6O3/c1-4-23(33)28-17-6-5-7-19(14-17)35-24-20(26)16-27-25(30-24)29-21-9-8-18(15-22(21)34-3)32-12-10-31(2)11-13-32/h4-9,14-16H,1,10-13H2,2-3H3,(H,28,33)(H,27,29,30)

N-{3-[(5-Chloro-2-{[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)oxy]phenyl}acrylamide - Physico-chemical Properties

Molecular FormulaC25H27ClN6O3
Molar Mass494.97
Density1.314
Solubility Soluble in DMSO (13 mg/ml) at 25 °C, water (<1 mg/ml) at 25 °C, and ethanol (<1 mg/
AppearanceWhite to beige powder
pKa12.78±0.70(Predicted)
Storage Condition-20℃
MDLMFCD16621244
UseAn EGFR phosphorylation inhibitor
In vitro studyWZ4002 also inhibits other EGFR genotypes, such as IC50 of 2 and 6 nM for E746_A750 and E746_A750/T790M, respectively. When WZ4002 acts on the wild type EGFR, the IC50 is 32 nM. WZ4002 inhibits the phosphorylation of EGFR, AKT and ERK1/2 in non-small cell lung cancer (NSCLC) cells. WZ4002 inhibits EGFR phosphorylation when acting on NIH-3T3 cells expressing different EGFRT790M mutant alleles. The dissociation constant of the kinase was determined, and the experimental group under the action of WZ4002 was 95% higher than the control group under the action of DMSO. WZ4002 has a higher effect on EGFR than WZ3146 due to obtaining an n-methoxy group when C2 aniline is substituted. Compared with quinazoline inhibitors, WZ4002 is 100 times less effective in the phosphorylation of wild-type EGFR. WZ4002 was much more effective in inhibiting the kinase activity of recombinant L858R/T790M protein EGFR than wild-type EGFR, while the inhibitory effects of HKI-272 and Gefitinib were just opposite to wz4002. In addition, the phosphorylation of EGFR of Src TKI-resistant H1975 cells and HCC827 cells was completely inhibited by the third generation EGFR TKI, wz4002.
In vivo studyA murine model containing the T790M mutation was treated for 2 weeks to study the efficacy of WZ4002, and it was found that WZ4002 treatment resulted in significant tumor regression compared to the control group. Treatment with low dose WZ4002, and high dose WZ4002, resulted in a decrease in mean uptake of 26% and 36%, respectively.

N-{3-[(5-Chloro-2-{[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)oxy]phenyl}acrylamide - Introduction

WZ4002 is a novel, mutation-selective EGFR inhibitor with an IC50 of 2 nM/8 nM when acting on EGFR(L858R)/(T790M); it has no inhibitory effect on ERBB2 phosphorylation (T798I).
Last Update：2022-10-16 17:12:46

N-{3-[(5-Chloro-2-{[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)oxy]phenyl}acrylamide - Reference Information

biological activity WZ4002 is a new, mutation-selective EGFR inhibitor with IC50 of 2 nM/8 nM when acting on EGFR(L858R)/(T790M); There is no inhibitory effect on ERBB2 phosphorylation (T798I).
Last Update：2024-04-09 20:49:11
N-{3-[(5-Chloro-2-{[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)oxy]phenyl}acrylamide
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Hubei YoungXin Pharmaceutical Tech Co.,Ltd.
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CAS: 1213269-23-8
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Shanghai Yuanye Bio-Technology Co., Ltd.
Product Name: WZ4002 Visit Supplier Webpage Request for quotation
CAS: 1213269-23-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409 Click to send a QQ message
Wechat: 18301782025
Hubei YoungXin Pharmaceutical Tech Co.,Ltd.
Spot supply
Product Name: WZ 4002 Visit Supplier Webpage Request for quotation
CAS: 1213269-23-8
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052 Click to send a QQ message
Wechat: 15671228036
Shanghai Yuanye Bio-Technology Co., Ltd.
Product Name: WZ4002 Visit Supplier Webpage Request for quotation
CAS: 1213269-23-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409 Click to send a QQ message
Wechat: 18301782025
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N-{3-[(5-Chloro-2-{[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)oxy]phenyl}acrylamide
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