698387-09-6,MFCD09752958
Catalog No.:AA0035AU

698387-09-6 | (2E)-N-(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide

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1mg
98%
in stock  
$6.00   $4.00
- +
10mg
98%
in stock  
$8.00   $6.00
- +
100mg
98%
in stock  
$28.00   $19.00
- +
250mg
98%
in stock  
$50.00   $35.00
- +
1g
98%
in stock  
$122.00   $86.00
- +
5g
97%
in stock  
$551.00 $386.00
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA0035AU
Chemical Name:
(2E)-N-(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide
CAS Number:
698387-09-6
Molecular Formula:
C30H29ClN6O3
Molecular Weight:
557.0427
MDL Number:
MFCD09752958
SMILES:
CCOc1cc2ncc(c(c2cc1NC(=O)/C=C/CN(C)C)Nc1ccc(c(c1)Cl)OCc1ccccn1)C#N
Properties
Properties
 
Form:
Solid  
MP:
185-187°C  
Storage:
2-8℃;  

Computed Properties
 
Complexity:
881  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
1  
Formal Charge:
0  
Heavy Atom Count:
40  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0  
Rotatable Bond Count:
11  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
4.9  

Downstream Synthesis Route

[1]JournalofMedicinalChemistry,2005,vol.48,p.1107-1131

[1]JournalofMedicinalChemistry,2005,vol.48,p.1107-1131

[1]JournalofMedicinalChemistry,2005,vol.48,p.1107-1131

[1]JournalofMedicinalChemistry,2005,vol.48,p.1107-1131

(E)-4-(dimethylamino)-2-butenoicacidhydrochloride 
  698387-09-6 

[1]JournalofMedicinalChemistry,2005,vol.48,p.1107-1131

Literature

Title: Adaptive Randomization of Neratinib in Early Breast Cancer.

Journal: The New England journal of medicine 20160707

Title: A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20131101

Title: Identification of potent Yes1 kinase inhibitors using a library screening approach.

Journal: Bioorganic & medicinal chemistry letters 20130801

Title: Dual blockade of HER2 - twice as good or twice as toxic?

Journal: Clinical oncology (Royal College of Radiologists (Great Britain)) 20121101

Title: New therapies in HER2-positive breast cancer: a major step towards a cure of the disease?

Journal: Cancer treatment reviews 20120801

Title: Interaction of the EGFR inhibitors gefitinib, vandetanib, pelitinib and neratinib with the ABCG2 multidrug transporter: implications for the emergence and reversal of cancer drug resistance.

Journal: Biochemical pharmacology 20120801

Title: Differential action of small molecule HER kinase inhibitors on receptor heterodimerization: therapeutic implications.

Journal: International journal of cancer 20120701

Title: A double-blind, randomized, multiple-dose, parallel-group study to characterize the occurrence of diarrhea following two different dosing regimens of neratinib, an irreversible pan-ErbB receptor tyrosine kinase inhibitor.

Journal: Cancer chemotherapy and pharmacology 20120701

Title: Neratinib reverses ATP-binding cassette B1-mediated chemotherapeutic drug resistance in vitro, in vivo, and ex vivo.

Journal: Molecular pharmacology 20120701

Title: Structural analysis of the EGFR TK domain and potential implications for EGFR targeted therapy.

Journal: International journal of oncology 20120601

Title: Neratinib (HKI-272) in the treatment of breast cancer.

Journal: Future oncology (London, England) 20120601

Title: Safety, efficacy and pharmacokinetics of neratinib (HKI-272) in Japanese patients with advanced solid tumors: a Phase 1 dose-escalation study.

Journal: Japanese journal of clinical oncology 20120401

Title: A genome-wide RNAi screen identifies novel targets of neratinib resistance leading to identification of potential drug resistant genetic markers.

Journal: Molecular bioSystems 20120401

Title: Preformulation stability study of the EGFR inhibitor HKI-272 (Neratinib) and mechanism of degradation.

Journal: Drug development and industrial pharmacy 20120301

Title: Comprehensive analysis of kinase inhibitor selectivity.

Journal: Nature biotechnology 20111030

Title: Beyond trastuzumab: new treatment options for HER2-positive breast cancer.

Journal: Breast (Edinburgh, Scotland) 20111001

Title: A genome-wide RNAi screen identifies novel targets of neratinib sensitivity leading to neratinib and paclitaxel combination drug treatments.

Journal: Molecular bioSystems 20110601

Title: The search for improved systemic therapy of non-small cell lung cancer--what are today's options?

Journal: Lung cancer (Amsterdam, Netherlands) 20110601

Title: Pharmacokinetics of oral neratinib during co-administration of ketoconazole in healthy subjects.

Journal: British journal of clinical pharmacology 20110401

Title: Cysteine mapping in conformationally distinct kinase nucleotide binding sites: application to the design of selective covalent inhibitors.

Journal: Journal of medicinal chemistry 20110310

Title: [Novel target therapies used in breast cancer management].

Journal: Voprosy onkologii 20110101

Title: Irreversible EGFR inhibitor EKB-569 targets low-LET γ-radiation-triggered rel orchestration and potentiates cell death in squamous cell carcinoma.

Journal: PloS one 20110101

Title: Reversible covalent binding of neratinib to human serum albumin in vitro.

Journal: Drug metabolism letters 20101201

Title: Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.

Journal: Chemistry & biology 20101124

Title: A single-dose, crossover, placebo- and moxifloxacin-controlled study to assess the effects of neratinib (HKI-272) on cardiac repolarization in healthy adult subjects.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20100801

Title: Characterization of HKI-272 covalent binding to human serum albumin.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100701

Title: Neratinib, an irreversible pan-ErbB receptor tyrosine kinase inhibitor: results of a phase II trial in patients with advanced non-small-cell lung cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20100620

Title: The role of irreversible EGFR inhibitors in the treatment of non-small cell lung cancer: overcoming resistance to reversible EGFR inhibitors.

Journal: Cancer investigation 20100501

Title: Neratinib, an irreversible ErbB receptor tyrosine kinase inhibitor, in patients with advanced ErbB2-positive breast cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20100310

Title: [Management of metastatic HER2-positive breast cancer: present and future].

Journal: Bulletin du cancer 20100301

Title: Irreversible pan-ErbB tyrosine kinase inhibitors and breast cancer: current status and future directions.

Journal: Cancer treatment reviews 20091201

Title: [New development in the treatment of breast cancer. II. Future anti-HER2 therapy].

Journal: Gan to kagaku ryoho. Cancer & chemotherapy 20091201

Title: Neratinib: an oral, irreversible dual EGFR/HER2 inhibitor for breast and non-small cell lung cancer.

Journal: Expert opinion on investigational drugs 20091101

Title: A phase I study with neratinib (HKI-272), an irreversible pan ErbB receptor tyrosine kinase inhibitor, in patients with solid tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090401

Title: Synthesis and stereochemical effects of pyrrolidinyl-acetylenic thieno[3,2-d]pyrimidines as EGFR and ErbB-2 inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20090101

Title: The development of HKI-272 and related compounds for the treatment of cancer.

Journal: Archiv der Pharmazie 20080801

Title: Second-generation epidermal growth factor receptor tyrosine kinase inhibitors in non-small cell lung cancer.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20080601

Title: The T790M 'gatekeeper' mutation in EGFR mediates resistance to low concentrations of an irreversible EGFR inhibitor.

Journal: Molecular cancer therapeutics 20080401

Title: Enzyme replacement therapy for Gaucher's disease in patient treated for non-small cell lung cancer.

Journal: Anticancer research 20080101

Title: HKI-272 in non small cell lung cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20070801

Title: The major lung cancer-derived mutants of ERBB2 are oncogenic and are associated with sensitivity to the irreversible EGFR/ERBB2 inhibitor HKI-272.

Journal: Oncogene 20070726

Title: Bronchial and peripheral murine lung carcinomas induced by T790M-L858R mutant EGFR respond to HKI-272 and rapamycin combination therapy.

Journal: Cancer cell 20070701

Title: Dual irreversible kinase inhibitors: quinazoline-based inhibitors incorporating two independent reactive centers with each targeting different cysteine residues in the kinase domains of EGFR and VEGFR-2.

Journal: Bioorganic & medicinal chemistry 20070601

Title: Allele-dependent variation in the relative cellular potency of distinct EGFR inhibitors.

Journal: Cancer biology & therapy 20070501

Title: Second-generation epidermal growth factor receptor tyrosine kinase inhibitors in non-small cell lung cancer.

Journal: The oncologist 20070301

Title: Pharmacology of epidermal growth factor inhibitors.

Journal: The International journal of biological markers 20070101

Title: Non-small-cell lung cancer and Ba/F3 transformed cells harboring the ERBB2 G776insV_G/C mutation are sensitive to the dual-specific epidermal growth factor receptor and ERBB2 inhibitor HKI-272.

Journal: Cancer research 20060701

Title: The impact of human EGFR kinase domain mutations on lung tumorigenesis and in vivo sensitivity to EGFR-targeted therapies.

Journal: Cancer cell 20060601

Title: EGF receptor mutations in lung cancer: from humans to mice and maybe back to humans.

Journal: Cancer cell 20060601

Title: Optimization of 6,7-disubstituted-4-(arylamino)quinoline-3-carbonitriles as orally active, irreversible inhibitors of human epidermal growth factor receptor-2 kinase activity.

Journal: Journal of medicinal chemistry 20050224

Title: Antitumor activity of HKI-272, an orally active, irreversible inhibitor of the HER-2 tyrosine kinase.

Journal: Cancer research 20040601

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SDS
Historical Records
Tags:698387-09-6 Molecular Formula|698387-09-6 MDL|698387-09-6 SMILES|698387-09-6 (2E)-N-(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide
Catalog No.: AA0035AU
698387-09-6,MFCD09752958
698387-09-6 | (2E)-N-(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide
Pack Size: 1mg
Purity: 98%
in stock
$6.00 $4.00
Pack Size: 10mg
Purity: 98%
in stock
$8.00 $6.00
Pack Size: 100mg
Purity: 98%
in stock
$28.00 $19.00
Pack Size: 250mg
Purity: 98%
in stock
$50.00 $35.00
Pack Size: 1g
Purity: 98%
in stock
$122.00 $86.00
Pack Size: 5g
Purity: 97%
in stock
$551.00 $386.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA0035AU
Chemical Name: (2E)-N-(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide
CAS Number: 698387-09-6
Molecular Formula: C30H29ClN6O3
Molecular Weight: 557.0427
MDL Number: MFCD09752958
SMILES: CCOc1cc2ncc(c(c2cc1NC(=O)/C=C/CN(C)C)Nc1ccc(c(c1)Cl)OCc1ccccn1)C#N
Properties
Form: Solid  
MP: 185-187°C  
Storage: 2-8℃;  
Complexity: 881  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 1  
Formal Charge: 0  
Heavy Atom Count: 40  
Hydrogen Bond Acceptor Count: 8  
Hydrogen Bond Donor Count: 2  
Isotope Atom Count: 0  
Rotatable Bond Count: 11  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 4.9  
Downstream Synthesis Route
524955-09-7    848133-88-0    698387-09-6 

[1]JournalofMedicinalChemistry,2005,vol.48,p.1107-1131

1056149-69-9    698387-09-6 

[1]JournalofMedicinalChemistry,2005,vol.48,p.1107-1131

214476-09-2    698387-09-6 

[1]JournalofMedicinalChemistry,2005,vol.48,p.1107-1131

848133-87-9    698387-09-6 

[1]JournalofMedicinalChemistry,2005,vol.48,p.1107-1131

(E)-4-(dimethylamino)-2-butenoicacidhydrochloride 
  698387-09-6 

[1]JournalofMedicinalChemistry,2005,vol.48,p.1107-1131

Literature fold

Title: Adaptive Randomization of Neratinib in Early Breast Cancer.

Journal: The New England journal of medicine20160707

Title: A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20131101

Title: Identification of potent Yes1 kinase inhibitors using a library screening approach.

Journal: Bioorganic & medicinal chemistry letters20130801

Title: Dual blockade of HER2 - twice as good or twice as toxic?

Journal: Clinical oncology (Royal College of Radiologists (Great Britain))20121101

Title: New therapies in HER2-positive breast cancer: a major step towards a cure of the disease?

Journal: Cancer treatment reviews20120801

Title: Interaction of the EGFR inhibitors gefitinib, vandetanib, pelitinib and neratinib with the ABCG2 multidrug transporter: implications for the emergence and reversal of cancer drug resistance.

Journal: Biochemical pharmacology20120801

Title: Differential action of small molecule HER kinase inhibitors on receptor heterodimerization: therapeutic implications.

Journal: International journal of cancer20120701

Title: A double-blind, randomized, multiple-dose, parallel-group study to characterize the occurrence of diarrhea following two different dosing regimens of neratinib, an irreversible pan-ErbB receptor tyrosine kinase inhibitor.

Journal: Cancer chemotherapy and pharmacology20120701

Title: Neratinib reverses ATP-binding cassette B1-mediated chemotherapeutic drug resistance in vitro, in vivo, and ex vivo.

Journal: Molecular pharmacology20120701

Title: Structural analysis of the EGFR TK domain and potential implications for EGFR targeted therapy.

Journal: International journal of oncology20120601

Title: Neratinib (HKI-272) in the treatment of breast cancer.

Journal: Future oncology (London, England)20120601

Title: Safety, efficacy and pharmacokinetics of neratinib (HKI-272) in Japanese patients with advanced solid tumors: a Phase 1 dose-escalation study.

Journal: Japanese journal of clinical oncology20120401

Title: A genome-wide RNAi screen identifies novel targets of neratinib resistance leading to identification of potential drug resistant genetic markers.

Journal: Molecular bioSystems20120401

Title: Preformulation stability study of the EGFR inhibitor HKI-272 (Neratinib) and mechanism of degradation.

Journal: Drug development and industrial pharmacy20120301

Title: Comprehensive analysis of kinase inhibitor selectivity.

Journal: Nature biotechnology20111030

Title: Beyond trastuzumab: new treatment options for HER2-positive breast cancer.

Journal: Breast (Edinburgh, Scotland)20111001

Title: A genome-wide RNAi screen identifies novel targets of neratinib sensitivity leading to neratinib and paclitaxel combination drug treatments.

Journal: Molecular bioSystems20110601

Title: The search for improved systemic therapy of non-small cell lung cancer--what are today's options?

Journal: Lung cancer (Amsterdam, Netherlands)20110601

Title: Pharmacokinetics of oral neratinib during co-administration of ketoconazole in healthy subjects.

Journal: British journal of clinical pharmacology20110401

Title: Cysteine mapping in conformationally distinct kinase nucleotide binding sites: application to the design of selective covalent inhibitors.

Journal: Journal of medicinal chemistry20110310

Title: [Novel target therapies used in breast cancer management].

Journal: Voprosy onkologii20110101

Title: Irreversible EGFR inhibitor EKB-569 targets low-LET γ-radiation-triggered rel orchestration and potentiates cell death in squamous cell carcinoma.

Journal: PloS one20110101

Title: Reversible covalent binding of neratinib to human serum albumin in vitro.

Journal: Drug metabolism letters20101201

Title: Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.

Journal: Chemistry & biology20101124

Title: A single-dose, crossover, placebo- and moxifloxacin-controlled study to assess the effects of neratinib (HKI-272) on cardiac repolarization in healthy adult subjects.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20100801

Title: Characterization of HKI-272 covalent binding to human serum albumin.

Journal: Drug metabolism and disposition: the biological fate of chemicals20100701

Title: Neratinib, an irreversible pan-ErbB receptor tyrosine kinase inhibitor: results of a phase II trial in patients with advanced non-small-cell lung cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20100620

Title: The role of irreversible EGFR inhibitors in the treatment of non-small cell lung cancer: overcoming resistance to reversible EGFR inhibitors.

Journal: Cancer investigation20100501

Title: Neratinib, an irreversible ErbB receptor tyrosine kinase inhibitor, in patients with advanced ErbB2-positive breast cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20100310

Title: [Management of metastatic HER2-positive breast cancer: present and future].

Journal: Bulletin du cancer20100301

Title: Irreversible pan-ErbB tyrosine kinase inhibitors and breast cancer: current status and future directions.

Journal: Cancer treatment reviews20091201

Title: [New development in the treatment of breast cancer. II. Future anti-HER2 therapy].

Journal: Gan to kagaku ryoho. Cancer & chemotherapy20091201

Title: Neratinib: an oral, irreversible dual EGFR/HER2 inhibitor for breast and non-small cell lung cancer.

Journal: Expert opinion on investigational drugs20091101

Title: A phase I study with neratinib (HKI-272), an irreversible pan ErbB receptor tyrosine kinase inhibitor, in patients with solid tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20090401

Title: Synthesis and stereochemical effects of pyrrolidinyl-acetylenic thieno[3,2-d]pyrimidines as EGFR and ErbB-2 inhibitors.

Journal: Bioorganic & medicinal chemistry letters20090101

Title: The development of HKI-272 and related compounds for the treatment of cancer.

Journal: Archiv der Pharmazie20080801

Title: Second-generation epidermal growth factor receptor tyrosine kinase inhibitors in non-small cell lung cancer.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer20080601

Title: The T790M 'gatekeeper' mutation in EGFR mediates resistance to low concentrations of an irreversible EGFR inhibitor.

Journal: Molecular cancer therapeutics20080401

Title: Enzyme replacement therapy for Gaucher's disease in patient treated for non-small cell lung cancer.

Journal: Anticancer research20080101

Title: HKI-272 in non small cell lung cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20070801

Title: The major lung cancer-derived mutants of ERBB2 are oncogenic and are associated with sensitivity to the irreversible EGFR/ERBB2 inhibitor HKI-272.

Journal: Oncogene20070726

Title: Bronchial and peripheral murine lung carcinomas induced by T790M-L858R mutant EGFR respond to HKI-272 and rapamycin combination therapy.

Journal: Cancer cell20070701

Title: Dual irreversible kinase inhibitors: quinazoline-based inhibitors incorporating two independent reactive centers with each targeting different cysteine residues in the kinase domains of EGFR and VEGFR-2.

Journal: Bioorganic & medicinal chemistry20070601

Title: Allele-dependent variation in the relative cellular potency of distinct EGFR inhibitors.

Journal: Cancer biology & therapy20070501

Title: Second-generation epidermal growth factor receptor tyrosine kinase inhibitors in non-small cell lung cancer.

Journal: The oncologist20070301

Title: Pharmacology of epidermal growth factor inhibitors.

Journal: The International journal of biological markers20070101

Title: Non-small-cell lung cancer and Ba/F3 transformed cells harboring the ERBB2 G776insV_G/C mutation are sensitive to the dual-specific epidermal growth factor receptor and ERBB2 inhibitor HKI-272.

Journal: Cancer research20060701

Title: The impact of human EGFR kinase domain mutations on lung tumorigenesis and in vivo sensitivity to EGFR-targeted therapies.

Journal: Cancer cell20060601

Title: EGF receptor mutations in lung cancer: from humans to mice and maybe back to humans.

Journal: Cancer cell20060601

Title: Optimization of 6,7-disubstituted-4-(arylamino)quinoline-3-carbonitriles as orally active, irreversible inhibitors of human epidermal growth factor receptor-2 kinase activity.

Journal: Journal of medicinal chemistry20050224

Title: Antitumor activity of HKI-272, an orally active, irreversible inhibitor of the HER-2 tyrosine kinase.

Journal: Cancer research20040601

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