Discovery of ErbB/HDAC inhibitors by combining the core pharmacophores of HDAC inhibitor vorinostat and kinase inhibitors vandetanib,BMS-690514,neratinib,and TAK-285
By combining the core pharmacophores of HDAC inhibitor vorinostat and kinase inhibitors vandetanib,BMS-690514,neratinib,and TAK-285 with 1,2,3-triazole as linker,eight novel 6-substituted-4-aminoquinazolin derivatives were synthesized and characterized by -1H NMR,-（13）C NMR,and high resolution mass...
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| Published in | Chinese chemical letters Vol. 28; no. 6; pp. 1220 - 1227 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier B.V
01.06.2017
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| Abstract | By combining the core pharmacophores of HDAC inhibitor vorinostat and kinase inhibitors vandetanib,BMS-690514,neratinib,and TAK-285 with 1,2,3-triazole as linker,eight novel 6-substituted-4-aminoquinazolin derivatives were synthesized and characterized by -1H NMR,-（13）C NMR,and high resolution mass spectrometry.Their inhibitory activities against five enzymes（VEGFR2,HER2,EGFR,HDAC1,and HDAC6） and five cancer cell lines（A549,BT-474,A431,SK-BR-3,and NCI-H1975） were evaluated.The bioassay results show that the introduction of triazole linked vorinostat-like segment dramatically changed the selectivity profiles of newly synthetic compounds relative to vandetanib,BMS-690514,neratinib,and TAK-285.Among them,compound 6b exerted outstanding enzymatic and cellular activities through its simultaneous and synergistic inhibitions on multiple pathways,which might have the great potential to confer the better benefits than single-targeted inhibitors in cancer therapy. |
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By merging the critical pharmacophore of kinase and HDAC inhibitors into one compound, a novel series of 6-(1,2,3-triazol-4-yl)-4-aminoquinazolin derivatives possessing hydroxamic acid moiety were synthesized as ErbB and HDAC dual-targeted inhibitors.
By combining the core pharmacophores of HDAC inhibitor vorinostat and kinase inhibitors vandetanib, BMS-690514, neratinib, and TAK-285 with 1,2,3-triazole as linker, eight novel 6-substituted-4-aminoquinazolin derivatives were synthesized and characterized by 1H NMR, 13C NMR, and high resolution mass spectrometry. Their inhibitory activities against five enzymes (VEGFR2, HER2, EGFR, HDAC1, and HDAC6) and five cancer cell lines (A549, BT-474, A431, SK-BR-3, and NCI-H1975) were evaluated. The bioassay results show that the introduction of triazole linked vorinostat-like segment dramatically changed the selectivity profiles of newly synthetic compounds relative to vandetanib, BMS-690514, neratinib, and TAK-285. Among them, compound 6b exerted outstanding enzymatic and cellular activities through its simultaneous and synergistic inhibitions on multiple pathways, which might have the great potential to confer the better benefits than single-targeted inhibitors in cancer therapy. By combining the core pharmacophores of HDAC inhibitor vorinostat and kinase inhibitors vandetanib,BMS-690514,neratinib,and TAK-285 with 1,2,3-triazole as linker,eight novel 6-substituted-4-aminoquinazolin derivatives were synthesized and characterized by -1H NMR,-（13）C NMR,and high resolution mass spectrometry.Their inhibitory activities against five enzymes（VEGFR2,HER2,EGFR,HDAC1,and HDAC6） and five cancer cell lines（A549,BT-474,A431,SK-BR-3,and NCI-H1975） were evaluated.The bioassay results show that the introduction of triazole linked vorinostat-like segment dramatically changed the selectivity profiles of newly synthetic compounds relative to vandetanib,BMS-690514,neratinib,and TAK-285.Among them,compound 6b exerted outstanding enzymatic and cellular activities through its simultaneous and synergistic inhibitions on multiple pathways,which might have the great potential to confer the better benefits than single-targeted inhibitors in cancer therapy. |
| Author | Chao Ding Dan Li Yan-Wei Wang Sai-Sai Han Chun-Mei Gao Chun-Yan Tan Yu-Yang Jiang |
| AuthorAffiliation | Department of Chemistry, Tsinghua University, Beijing 100084, China The State Key Laboratory Breeding Base-Shenzhen Key Laboratory of Chemical Biology, The Graduate School at Shenzhen, Tsinghua University, Shenzhen518055, China Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084, China |
| Author_xml | – sequence: 1 givenname: Chao surname: Ding fullname: Ding, Chao organization: Department of Chemistry, Tsinghua University, Beijing 100084, China – sequence: 2 givenname: Dan surname: Li fullname: Li, Dan organization: Department of Chemistry, Tsinghua University, Beijing 100084, China – sequence: 3 givenname: Yan-Wei surname: Wang fullname: Wang, Yan-Wei organization: Department of Chemistry, Tsinghua University, Beijing 100084, China – sequence: 4 givenname: Sai-Sai surname: Han fullname: Han, Sai-Sai organization: Department of Chemistry, Tsinghua University, Beijing 100084, China – sequence: 5 givenname: Chun-Mei surname: Gao fullname: Gao, Chun-Mei organization: The State Key Laboratory Breeding Base-Shenzhen Key Laboratory of Chemical Biology, The Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055, China – sequence: 6 givenname: Chun-Yan surname: Tan fullname: Tan, Chun-Yan email: tancy@sz.tsinghua.edu.cn organization: The State Key Laboratory Breeding Base-Shenzhen Key Laboratory of Chemical Biology, The Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055, China – sequence: 7 givenname: Yu-Yang surname: Jiang fullname: Jiang, Yu-Yang email: jiangyy@sz.tsinghua.edu.cn organization: The State Key Laboratory Breeding Base-Shenzhen Key Laboratory of Chemical Biology, The Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055, China |
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| Notes | 11-2710/O6 By combining the core pharmacophores of HDAC inhibitor vorinostat and kinase inhibitors vandetanib,BMS-690514,neratinib,and TAK-285 with 1,2,3-triazole as linker,eight novel 6-substituted-4-aminoquinazolin derivatives were synthesized and characterized by -1H NMR,-（13）C NMR,and high resolution mass spectrometry.Their inhibitory activities against five enzymes（VEGFR2,HER2,EGFR,HDAC1,and HDAC6） and five cancer cell lines（A549,BT-474,A431,SK-BR-3,and NCI-H1975） were evaluated.The bioassay results show that the introduction of triazole linked vorinostat-like segment dramatically changed the selectivity profiles of newly synthetic compounds relative to vandetanib,BMS-690514,neratinib,and TAK-285.Among them,compound 6b exerted outstanding enzymatic and cellular activities through its simultaneous and synergistic inhibitions on multiple pathways,which might have the great potential to confer the better benefits than single-targeted inhibitors in cancer therapy. Anticancer Kinase HDAC Multitarget Selectivity |
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| Title | Discovery of ErbB/HDAC inhibitors by combining the core pharmacophores of HDAC inhibitor vorinostat and kinase inhibitors vandetanib,BMS-690514,neratinib,and TAK-285 |
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