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Synthesis and biological evaluation of 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-substituted-phenoxy)pyrimidines as dual EGFR/ErbB-2 kinase inhibitors

A series of 4,6-disubstituted pyrimidines derivatives were designed and synthesized as dual EGFR/ErbB-2 inhibitors. 4-[3-Chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-acrylamidophenoxy)pyrimidine and 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-{3-[6-(4-amino)pyrimidinyl]amino)phenoxy}pyrimidine had the... Full description

Journal Title: Bioorganic & Medicinal Chemistry 15 January 2012, Vol.20(2), pp.877-885
Main Author: Li, Siyuan
Other Authors: Guo, Chunying , Zhao, Hongli , Tang, Yun , Lan, Minbo
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0968-0896 ; E-ISSN: 1464-3391 ; DOI: 10.1016/j.bmc.2011.11.056
Link: https://www.sciencedirect.com/science/article/pii/S0968089611009928
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recordid: elsevier_sdoi_10_1016_j_bmc_2011_11_056
title: Synthesis and biological evaluation of 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-substituted-phenoxy)pyrimidines as dual EGFR/ErbB-2 kinase inhibitors
format: Article
creator:
  • Li, Siyuan
  • Guo, Chunying
  • Zhao, Hongli
  • Tang, Yun
  • Lan, Minbo
subjects:
  • Pyrimidine
  • Egfr
  • Erbb-2
  • Inhibitor
  • Docking
  • Medicine
  • Chemistry
  • Anatomy & Physiology
ispartof: Bioorganic & Medicinal Chemistry, 15 January 2012, Vol.20(2), pp.877-885
description: A series of 4,6-disubstituted pyrimidines derivatives were designed and synthesized as dual EGFR/ErbB-2 inhibitors. 4-[3-Chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-acrylamidophenoxy)pyrimidine and 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-{3-[6-(4-amino)pyrimidinyl]amino)phenoxy}pyrimidine had the best biological activities in vitro. Docking simulation was performed to explore the binding model of these compounds with EGFR. A series of 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-substituted-phenoxy)pyrimidine derivatives were elaborately designed based on the skeleton of Lapatinib, and evaluated for their potential to inhibit epidermal growth factor receptor (EGFR) and ErbB-2 tyrosine kinase activities and antiproliferative activities against A431 and SKOV-3 cell lines. Among these synthesized pyrimidine derivatives, 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-acrylamidophenoxy)pyrimidine ( ), 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-cyanoacetamidophenoxy)pyrimidine...
language: eng
source:
identifier: ISSN: 0968-0896 ; E-ISSN: 1464-3391 ; DOI: 10.1016/j.bmc.2011.11.056
fulltext: fulltext
issn:
  • 0968-0896
  • 09680896
  • 1464-3391
  • 14643391
url: Link


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titleSynthesis and biological evaluation of 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-substituted-phenoxy)pyrimidines as dual EGFR/ErbB-2 kinase inhibitors
creatorLi, Siyuan ; Guo, Chunying ; Zhao, Hongli ; Tang, Yun ; Lan, Minbo
ispartofBioorganic & Medicinal Chemistry, 15 January 2012, Vol.20(2), pp.877-885
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subjectPyrimidine ; Egfr ; Erbb-2 ; Inhibitor ; Docking ; Medicine ; Chemistry ; Anatomy & Physiology
descriptionA series of 4,6-disubstituted pyrimidines derivatives were designed and synthesized as dual EGFR/ErbB-2 inhibitors. 4-[3-Chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-acrylamidophenoxy)pyrimidine and 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-{3-[6-(4-amino)pyrimidinyl]amino)phenoxy}pyrimidine had the best biological activities in vitro. Docking simulation was performed to explore the binding model of these compounds with EGFR. A series of 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-substituted-phenoxy)pyrimidine derivatives were elaborately designed based on the skeleton of Lapatinib, and evaluated for their potential to inhibit epidermal growth factor receptor (EGFR) and ErbB-2 tyrosine kinase activities and antiproliferative activities against A431 and SKOV-3 cell lines. Among these synthesized pyrimidine derivatives, 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-acrylamidophenoxy)pyrimidine ( ), 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-cyanoacetamidophenoxy)pyrimidine...
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titleSynthesis and biological evaluation of 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-substituted-phenoxy)pyrimidines as dual EGFR/ErbB-2 kinase inhibitors
description

A series of 4,6-disubstituted pyrimidines derivatives were designed and synthesized as dual EGFR/ErbB-2 inhibitors. 4-[3-Chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-acrylamidophenoxy)pyrimidine and 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-{3-[6-(4-amino)pyrimidinyl]amino)phenoxy}pyrimidine had the best biological activities in vitro. Docking simulation was performed to explore the binding model of these compounds with EGFR.

A series of 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-substituted-phenoxy)pyrimidine derivatives were elaborately designed based on the skeleton of Lapatinib, and evaluated for their potential to inhibit epidermal growth factor receptor (EGFR) and ErbB-2 tyrosine kinase activities and antiproliferative activities against A431 and SKOV-3 cell lines. Among these synthesized pyrimidine derivatives, 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-acrylamidophenoxy)pyrimidine (

), 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-cyanoacetamidophenoxy)pyrimidine...

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A series of 4,6-disubstituted pyrimidines derivatives were designed and synthesized as dual EGFR/ErbB-2 inhibitors. 4-[3-Chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-acrylamidophenoxy)pyrimidine and 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-{3-[6-(4-amino)pyrimidinyl]amino)phenoxy}pyrimidine had the best biological activities in vitro. Docking simulation was performed to explore the binding model of these compounds with EGFR.

A series of 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-substituted-phenoxy)pyrimidine derivatives were elaborately designed based on the skeleton of Lapatinib, and evaluated for their potential to inhibit epidermal growth factor receptor (EGFR) and ErbB-2 tyrosine kinase activities and antiproliferative activities against A431 and SKOV-3 cell lines. Among these synthesized pyrimidine derivatives, 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-acrylamidophenoxy)pyrimidine (

), 4-[3-chloro-4-(3-fluorobenzyloxy)anilino]-6-(3-cyanoacetamidophenoxy)pyrimidine...

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doi10.1016/j.bmc.2011.11.056
lad01Bioorganic & Medicinal Chemistry
date2012-01-15