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229476-53-3,MFCD18782710
Catalog No.:AA002LJP

229476-53-3 | Ebe-a22

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  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA002LJP
Chemical Name:
Ebe-a22
CAS Number:
229476-53-3
Molecular Formula:
C17H16BrN3O2
Molecular Weight:
374.2318
MDL Number:
MFCD18782710
SMILES:
COc1cc2c(cc1OC)ncnc2N(c1cccc(c1)Br)C
Properties
Computed Properties
 
Complexity:
387  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
5  
Rotatable Bond Count:
4  
XLogP3:
4.2  

Literature

Title: Role of EGF receptor ligands in TCDD-induced EGFR down-regulation and cellular proliferation.

Journal: Chemico-biological interactions 20160625

Title: Pb²⁺ induced IL-8 gene expression by extracellular signal-regulated kinases and the transcription factor, activator protein 1, in human gastric carcinoma cells.

Journal: Environmental toxicology 20150301

Title: Tyrosine kinase inhibitors influence ABCG2 expression in EGFR-positive MDCK BCRP cells via the PI3K/Akt signaling pathway.

Journal: ChemMedChem 20120401

Title: Inhibition of epidermal growth factor receptor tyrosine kinase ameliorates collagen-induced arthritis.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20120401

Title: Therapeutic and preventive effects of an epidermal growth factor receptor inhibitor on oral squamous cell carcinoma.

Journal: The Journal of international medical research 20120101

Title: Molecular imaging with 11C-PD153035 PET/CT predicts survival in non-small cell lung cancer treated with EGFR-TKI: a pilot study.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20111001

Title: EGFR signaling suppresses osteoblast differentiation and inhibits expression of master osteoblastic transcription factors Runx2 and Osterix.

Journal: Journal of cellular biochemistry 20110701

Title: Impact of aryloxy-linked quinazolines: a novel series of selective VEGFR-2 receptor tyrosine kinase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20110401

Title: A novel hybrid peptide targeting EGFR-expressing cancers.

Journal: European journal of cancer (Oxford, England : 1990) 20110301

Title: Evaluation of radioiodinated quinazoline derivative as a new ligand for EGF receptor tyrosine kinase activity using SPECT.

Journal: Annals of nuclear medicine 20110201

Title: Determining the binding mode and binding affinity constant of tyrosine kinase inhibitor PD153035 to DNA using optical tweezers.

Journal: Biochemical and biophysical research communications 20110107

Title: Identification of the amyloid β-protein precursor and cystatin C as novel epidermal growth factor receptor regulated secretory proteins in nasopharyngeal carcinoma by proteomics.

Journal: Journal of proteome research 20101203

Title: Design, synthesis, and DNA-binding of N-alkyl(anilino)quinazoline derivatives.

Journal: Journal of medicinal chemistry 20101125

Title: Synthesis and initial tumor affinity testing of iodine-123 labelled EGFR-affine agents as potential imaging probes for hormone-refractory prostate cancer.

Journal: European journal of medicinal chemistry 20100901

Title: Signaling through erbB receptors is a critical functional regulator in the mature cochlea.

Journal: The European journal of neuroscience 20100901

Title: Epidermal growth factor receptor tyrosine kinase inhibitors induce CCL2 and CCL5 via reduction in IL-1R2 in keratinocytes.

Journal: Experimental dermatology 20100801

Title: Gastrin-releasing peptide promotes the growth of HepG2 cells via EGFR-independent ERK1/2 activation.

Journal: Oncology reports 20100801

Title: F84, a quinazoline derivative, exhibits high potent antitumor activity against human gynecologic malignancies.

Journal: Investigational new drugs 20100401

Title: B5, a novel pyrrole-substituted indolinone, exerts potent antitumor efficacy through G2/M cell cycle arrest.

Journal: Investigational new drugs 20100201

Title: Potent cardioprotective effect of the 4-anilinoquinazoline derivative PD153035: involvement of mitochondrial K(ATP) channel activation.

Journal: PloS one 20100101

Title: EGFR tyrosine kinase inhibitor (PD153035) improves glucose tolerance and insulin action in high-fat diet-fed mice.

Journal: Diabetes 20091201

Title: EFEMP1 binds the EGF receptor and activates MAPK and Akt pathways in pancreatic carcinoma cells.

Journal: Biological chemistry 20091201

Title: The unfolded protein response is activated in differentiating epidermal keratinocytes.

Journal: The Journal of investigative dermatology 20090901

Title: Molecular imaging of EGFR: it's time to go beyond receptor expression.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20090701

Title: Lead acetate induces EGFR activation upstream of SFK and PKCalpha linkage to the Ras/Raf-1/ERK signaling.

Journal: Toxicology and applied pharmacology 20090301

Title: Antitumor activity of a novel EGFR tyrosine kinase inhibitor against human lung carcinoma in vitro and in vivo.

Journal: Investigational new drugs 20090201

Title: Growth factors involved in aqueous humour-induced lens cell proliferation.

Journal: Growth factors (Chur, Switzerland) 20090201

Title: PET-based biodistribution and radiation dosimetry of epidermal growth factor receptor-selective tracer 11C-PD153035 in humans.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20090201

Title: Priming with EGFR tyrosine kinase inhibitor and EGF sensitizes ovarian cancer cells to respond to chemotherapeutical drugs.

Journal: Cancer letters 20080808

Title: HTS assays using a disease-relevant cell model for interrogating the MAP kinase pathway initiated by multiple receptors.

Journal: Assay and drug development technologies 20080601

Title: [Molecular imaging of epidermal growth factor receptor in glioma-bearing rats].

Journal: Zhonghua zhong liu za zhi [Chinese journal of oncology] 20080501

Title: Biochemical assay-based selectivity profiling of clinically relevant kinase inhibitors on mutant forms of EGF receptor.

Journal: Journal of receptor and signal transduction research 20080101

Title: Leptin stimulates the proliferation of human oesophageal adenocarcinoma cells via HB-EGF and Tgfalpha mediated transactivation of the epidermal growth factor receptor.

Journal: British journal of biomedical science 20080101

Title: The DNA-binding epidermal growth factor-receptor inhibitor PD153035 and other DNA-intercalating cytotoxic drugs reactivate the expression of the retinoic acid receptor-beta tumor-suppressor gene in breast cancer cells.

Journal: Differentiation; research in biological diversity 20071101

Title: Assessment of 11C-labeled-4-N-(3-bromoanilino)-6,7-dimethoxyquinazoline as a positron emission tomography agent to monitor epidermal growth factor receptor expression.

Journal: Cancer science 20070901

Title: Signaling pathway for 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced TNF-alpha production in differentiated THP-1 human macrophages.

Journal: Experimental & molecular medicine 20070831

Title: Further characterization of the epidermal growth factor receptor ligand 11C-PD153035.

Journal: Chinese medical journal 20070605

Title: Upregulation of retinoic acid receptor-beta by the epidermal growth factor-receptor inhibitor PD153035 is not mediated by blockade of ErbB pathways.

Journal: Journal of cellular physiology 20070601

Title: Protein C is an autocrine growth factor for human skin keratinocytes.

Journal: The Journal of biological chemistry 20070504

Title: [Expressions of epidermal growth factor receptor signaling substances in gastric mucosal cells influenced by serum derived from rats treated with electroacupuncture at stomach meridian acupoints].

Journal: Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine 20070501

Title: Blockage of epidermal growth factor receptor by quinazoline tyrosine kinase inhibitors suppresses growth of human hepatocellular carcinoma.

Journal: Cancer letters 20070408

Title: EGF receptor clustering is induced by a 0.4 mT power frequency magnetic field and blocked by the EGF receptor tyrosine kinase inhibitor PD153035.

Journal: Bioelectromagnetics 20070401

Title: Immortalization of human urothelial cells by human papillomavirus type 16 E6 and E7 genes in a defined serum-free system.

Journal: Cell proliferation 20070401

Title: Control of tight junctional sealing: role of epidermal growth factor.

Journal: American journal of physiology. Renal physiology 20070201

Title: Epidermal growth factor receptor inhibition sensitizes renal cell carcinoma cells to the cytotoxic effects of bortezomib.

Journal: Molecular cancer therapeutics 20070101

Title: Signal pathways involved in the regulation of prostaglandin E synthase-1 in human gingival fibroblasts.

Journal: Cellular signalling 20061201

Title: The tyrosine kinase inhibitor PD153035: implication of labeling position on radiometabolites formed in vitro.

Journal: Nuclear medicine and biology 20061101

Title: UVB radiation induces expression of HIF-1alpha and VEGF through the EGFR/PI3K/DEC1 pathway.

Journal: International journal of molecular medicine 20061001

Title: PPARgamma-regulated tight junction development during human urothelial cytodifferentiation.

Journal: Journal of cellular physiology 20060801

Title: Inhibition of EGFR/PI3K/AKT cell survival pathway promotes TSA's effect on cell death and migration in human ovarian cancer cells.

Journal: International journal of oncology 20060701

Title: Amphiregulin contributes to the transformed phenotype of human hepatocellular carcinoma cells.

Journal: Cancer research 20060615

Title: The epidermal growth factor receptor (EGFR)-S442F mutant displays increased affinity for neuregulin-2beta and agonist-independent coupling with downstream signalling events.

Journal: The Biochemical journal 20060515

Title: Indole-3-carbinol-induced death in cancer cells involves EGFR downregulation and is exacerbated in a 3D environment.

Journal: Apoptosis : an international journal on programmed cell death 20060501

Title: COX-2-mediated stimulation of the lymphangiogenic factor VEGF-C in human breast cancer.

Journal: British journal of cancer 20060424

Title: Transforming growth factor alpha attenuates the functional expression of AMPA receptors in cortical GABAergic neurons.

Journal: Molecular and cellular neurosciences 20060401

Title: Suppression of pro-metastasis phenotypes expression in malignant pleural mesothelioma by the PI3K inhibitor LY294002 or the MEK inhibitor UO126.

Journal: Anticancer research 20060101

Title: Asbestos-induced activation of cell signaling pathways in human bronchial epithelial cells.

Journal: Experimental lung research 20060101

Title: Epidermal growth factor-, transforming growth factor-beta-, retinoic acid- and 1,25-dihydroxyvitamin D3-regulated expression of the novel protein PTPIP51 in keratinocytes.

Journal: Cells, tissues, organs 20060101

Title: Transient activation of EGFR/AKT cell survival pathway and expression of survivin contribute to reduced sensitivity of human melanoma cells to betulinic acid.

Journal: International journal of oncology 20050901

Title: Mechanism of thymus- and activation-regulated chemokine (TARC)/CCL17 production and its modulation by roxithromycin.

Journal: The Journal of investigative dermatology 20050901

Title: Up-regulation in endothelin-1 by Helicobacter pylori lipopolysaccharide interferes with gastric mucin synthesis via epidermal growth factor receptor transactivation.

Journal: Scandinavian journal of gastroenterology 20050801

Title: Antagonistic regulation of swelling-activated Cl- current in rabbit ventricle by Src and EGFR protein tyrosine kinases.

Journal: American journal of physiology. Heart and circulatory physiology 20050601

Title: Autocrine regulation of human urothelial cell proliferation and migration during regenerative responses in vitro.

Journal: Experimental cell research 20050515

Title: The selective epidermal growth factor receptor tyrosine kinase inhibitor PD153035 suppresses expression of prometastasis phenotypes in malignant pleural mesothelioma cells in vitro.

Journal: The Journal of thoracic and cardiovascular surgery 20050501

Title: An EGF receptor inhibitor induces RAR-beta expression in breast and ovarian cancer cells.

Journal: Biochemical and biophysical research communications 20050422

Title: Inhibition of the epidermal growth factor receptor increases expression of genes that stimulate inflammation, apoptosis, and cell attachment.

Journal: Molecular cancer therapeutics 20050401

Title: High performance liquid chromatography analysis of a 4-anilinoquinazoline derivative (PD153035), a specific inhibitor of the epidermal growth factor receptor tyrosine kinase, in rat plasma.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050325

Title: Epidermal and hepatocyte growth factors, but not keratinocyte growth factor, modulate protein kinase Calpha translocation to the plasma membrane through 15(S)-hydroxyeicosatetraenoic acid synthesis.

Journal: The Journal of biological chemistry 20050304

Title: Global kinase screening. Applications of frontal affinity chromatography coupled to mass spectrometry in drug discovery.

Journal: Analytical chemistry 20050301

Title: Comparison of ELISA-based tyrosine kinase assays for screening EGFR inhibitors.

Journal: Journal of receptor and signal transduction research 20050101

Title: [Role of PD153035 in the induction of apoptosis of XG-1 myeloma cell line].

Journal: Zhongguo yi xue ke xue yuan xue bao. Acta Academiae Medicinae Sinicae 20041001

Title: Porphyromonas gingivalis lipopolysaccharide-induced up-regulation in endothelin-1 interferes with salivary mucin synthesis via epidermal growth factor receptor transactivation.

Journal: IUBMB life 20041001

Title: Co-inhibition of epidermal growth factor receptor and type 1 insulin-like growth factor receptor synergistically sensitizes human malignant glioma cells to CD95L-induced apoptosis.

Journal: Biochemical and biophysical research communications 20040827

Title: Salivary phospholipid secretion in response to beta-adrenergic stimulation is mediated by Src kinase-dependent epidermal growth factor receptor transactivation.

Journal: Biochemical and biophysical research communications 20040521

Title: Prevention of renal vascular and glomerular fibrosis by epidermal growth factor receptor inhibition.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20040501

Title: Activation of peroxisome proliferator-activated receptor-gamma reverses squamous metaplasia and induces transitional differentiation in normal human urothelial cells.

Journal: The American journal of pathology 20040501

Title: Role of PPARgamma and EGFR signalling in the urothelial terminal differentiation programme.

Journal: Journal of cell science 20040415

Title: Heparin-binding epidermal growth factor cleavage mediates zinc-induced epidermal growth factor receptor phosphorylation.

Journal: American journal of respiratory cell and molecular biology 20040401

Title: Regulation of parathyroid hormone-related protein gene expression by epidermal growth factor-family ligands in primary human keratinocytes.

Journal: The Journal of endocrinology 20040401

Title: EphB4 signaling is capable of mediating ephrinB2-induced inhibition of cell migration.

Journal: Biochemical and biophysical research communications 20040102

Title: Evaluation of novel epidermal growth factor receptor tyrosine kinase inhibitors.

Journal: Breast cancer research and treatment 20040101

Title: Resistance to small molecule inhibitors of epidermal growth factor receptor in malignant gliomas.

Journal: Cancer research 20031101

Title: Expression of ErbB receptors in ES cell-derived cardiomyocytes.

Journal: Biochemical and biophysical research communications 20030912

Title: Mechanisms of Zn(2+)-induced signal initiation through the epidermal growth factor receptor.

Journal: Toxicology and applied pharmacology 20030815

Title: Synergistic antiproliferative and apoptotic effects induced by epidermal growth factor receptor and protein kinase a inhibitors in human prostatic cancer cell lines.

Journal: International journal of cancer 20030810

Title: Regulation of TGF-alpha-induced activation of AP-1 in the aging gastric mucosa.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20030801

Title: Epidermal growth factor inhibition of c-Myc-mediated apoptosis through Akt and Erk involves Bcl-xL upregulation in mammary epithelial cells.

Journal: Experimental cell research 20030715

Title: Mutation of threonine 766 in the epidermal growth factor receptor reveals a hotspot for resistance formation against selective tyrosine kinase inhibitors.

Journal: The Journal of biological chemistry 20030425

Title: Quantitative image analysis of cellular protein translocation induced by magnetic microspheres: application to the EGF receptor.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20030301

Title: Epidermal growth factor receptor trans-activation mediates the tonic and fibrogenic effects of endothelin in the aortic wall of transgenic mice.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20030201

Title: PET screening of anticancer drugs. A faster route to drug/target evaluations in vivo.

Journal: Methods in molecular medicine 20030101

Title: Enhanced antiangiogenic therapy of squamous cell carcinoma by combined endostatin and epidermal growth factor receptor-antisense therapy.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20021101

Title: Heparin-binding EGF-like growth factor gene transcription regulated by Cdx2 in the intestinal epithelium.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20021001

Title: Activation of proteinase-activated receptor 1 stimulates epithelial chloride secretion through a unique MAP kinase- and cyclo-oxygenase-dependent pathway.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20021001

Title: 4-anilino-3-quinolinecarbonitriles: an emerging class of kinase inhibitors.

Journal: Current topics in medicinal chemistry 20020901

Title: Regulation of Akt by EGF-R inhibitors, a possible mechanism of EGF-R inhibitor-enhanced TRAIL-induced apoptosis.

Journal: Biochemical and biophysical research communications 20020712

Title: Okadaic acid-induced EGF receptor and MAP kinase activation does not require reactive oxygen species in primary keratinocytes.

Journal: Archives of dermatological research 20020701

Title: EBV-expressing AGS gastric carcinoma cell sublines present increased motility and invasiveness.

Journal: International journal of cancer 20020610

Title: Establishment and characterization of acquired resistance to the farnesyl protein transferase inhibitor R115777 in a human colon cancer cell line.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20020601

Title: Autocrine-mediated activation of STAT3 correlates with cell proliferation in breast carcinoma lines.

Journal: The Journal of biological chemistry 20020517

Title: Role of Ras in metal-induced EGF receptor signaling and NF-kappaB activation in human airway epithelial cells.

Journal: American journal of physiology. Lung cellular and molecular physiology 20020501

Title: Regulation of cultured rat hepatocyte proliferation by stellate cells.

Journal: Journal of hepatology 20020501

Title: Prostaglandin E2 transactivates EGF receptor: a novel mechanism for promoting colon cancer growth and gastrointestinal hypertrophy.

Journal: Nature medicine 20020301

Title: Activation of EGF receptors mediates pulmonary vasoconstriction induced by residual oil fly ash.

Journal: Experimental lung research 20020101

Title: Transactivation of the epidermal growth factor receptor is involved in 12-O-tetradecanoylphorbol-13-acetate-induced signal transduction.

Journal: The Journal of biological chemistry 20011214

Title: Lymnaea epidermal growth factor promotes axonal regeneration in CNS organ culture.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20011201

Title: Induction of EGFR-dependent and EGFR-independent signaling pathways by ultraviolet A irradiation.

Journal: DNA and cell biology 20011201

Title: 1,4-dioxane-fused 4-anilinoquinazoline as inhibitors of epidermal growth factor receptor kinase.

Journal: Archiv der Pharmazie 20011101

Title: Epidermal growth factor receptor signaling and the invasive phenotype of ovarian carcinoma cells.

Journal: Journal of the National Cancer Institute 20010919

Title: Signaling-inactive epidermal growth factor receptor/ligand complexes in intact carcinoma cells by quinazoline tyrosine kinase inhibitors.

Journal: Cancer research 20010801

Title: Differential utilization and localization of ErbB receptor tyrosine kinases in skin compared to normal and malignant keratinocytes.

Journal: Neoplasia (New York, N.Y.) 20010701

Title: Epidermal growth factor induction of apolipoprotein A-I is mediated by the Ras-MAP kinase cascade and Sp1.

Journal: The Journal of biological chemistry 20010427

Title: DNA interaction of the tyrosine protein kinase inhibitor PD153035 and its N-methyl analogue.

Journal: Biochemistry 20010417

Title: Transmodulation of epidermal growth factor receptor mediates IL-1 beta-induced MMP-1 expression in cultured human keratinocytes.

Journal: International journal of molecular medicine 20010301

Title: BIBX1382BS, but not AG1478 or PD153035, inhibits the ErbB kinases at different concentrations in intact cells.

Journal: Biochemical and biophysical research communications 20010216

Title: Role of transforming growth factor-alpha in von Hippel--Lindau (VHL)(-/-) clear cell renal carcinoma cell proliferation: a possible mechanism coupling VHL tumor suppressor inactivation and tumorigenesis.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20010213

Title: A role for endogenous TGFalpha and associated signaling pathways in the differentiation of lens fiber cells.

Journal: Journal of cellular physiology 20010201

Title: EGF receptor crosstalks with cytokine receptors leading to the activation of c-Jun kinase in response to UV irradiation in human keratinocytes.

Journal: Cellular signalling 20010201

Title: Tyrosine kinase inhibitors. 8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor.

Journal: Journal of medicinal chemistry 19960105

Title: Identification of cariogenic bacteria by fluorescent antibody and other techniques: an international symposium. New York City, April 3-4, 1975. Concluding remarks: the current status of the National Caries Program.

Journal: Journal of dental research 19760101

Title: Goossens JF, et al. DNA interaction of the tyrosine protein kinase inhibitor PD153035 and its N-methyl analogue. Biochemistry. 2001 Apr 17;40(15):4663-71.

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Tags:229476-53-3 Molecular Formula|229476-53-3 MDL|229476-53-3 SMILES|229476-53-3 Ebe-a22