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Discovery of N-(3-(5-((3-acrylamido-4-(morpholine-4-carbonyl) phenyl)amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-methylphenyl)-4-(tert-butyl)benzamide (CHMFL-BTK-01) as a highly selective irreversible Bruton's tyrosine kinase (BTK) inhibitor
Liang, Qianmao1,2; Chen, Yongfei2,3; Yu, Kailin2,4; Chen, Cheng2,3; Zhang, Shouxiang5,6; Wang, Aoli2,4; Wang, Wei2,3; Wu, Hong2,4; Liu, Xiaochuan1,2; Wang, Beilei2,3; Wang, Li2,3; Hu, Zhenquan2,3; Wang, Wenchao2,3; Ren, Tao7; Zhang, Shanchun3,8; Liu, Qingsong2,3,4,7; Yun, Cai-Hong5,6; Liu, Jing2,3
2017-05-05
Source PublicationEUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume131Pages:107-125
AbstractCurrently there are several irreversible BTK inhibitors targeting Cys481 residue under preclinical or clinical development. However, most of these inhibitors also targeted other Idnases such as BMX, JAK3, and EGFR that bear the highly similar active cysteine residues. Through a structure-based drug design approach, we discovered a highly potent (IC50: 7 nM) irreversible BTK inhibitor compound 9 (CHMFL-BTK-01), which displayed a high selectivity profile in KINOMEscan (S score (35) = 0.00) among 468 kinases/mutants at the concentration of 1 mu M. Compound 9 completely abolished BMX, JAK3 and EGFR's activity. Both X-ray crystal structure and cysteine-serine mutation mediated rescue experiment confirmed 9's irreversible binding mode. 9 also potently inhibited BTK Y223 auto-phosphorylation (EC50: <30 nM), arrested cell cycle in G0/G1 phase and induced apoptosis in U2932 and Pfeiffer cells. We believe these features would make 9 a good pharmacological tool to study the BTK related pathology. (C) 2017 Elsevier Masson SAS. All rights reserved.
SubtypeArticle
KeywordBtk Irreversible Inhibitor Kinase Inhibitor Structure-activity Relationship B-cell Lymphoma
WOS HeadingsScience & Technology ; Life Sciences & Biomedicine
Funding OrganizationYouth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; 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Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; 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Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; 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DOI10.1016/j.ejmech.2017.03.001
WOS KeywordX-LINKED AGAMMAGLOBULINEMIA ; B-CELL ; RHEUMATOID-ARTHRITIS ; ACTIVATION ; COVALENT ; IBRUTINIB ; POTENT ; GENE ; PROLIFERATION ; EXPRESSION
Indexed BySCI
Language英语
Funding OrganizationYouth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; 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Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; Youth Foundation of National Natural Science Foundation of China(21402207) ; 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National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; National Program for Support of Top-notch Young Professionals ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; Hundred Talents Program of the Chinese Academy of Sciences ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Basic Research Program (973) of China(2012CB917202) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; National Natural Science Foundation of China(31270769) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007) ; Hefei Science Center CAS(2016HSCIU007)
WOS Research AreaPharmacology & Pharmacy
WOS SubjectChemistry, Medicinal
WOS IDWOS:000399266500008
Citation statistics
Cited Times:7[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.hfcas.ac.cn:8080/handle/334002/33394
Collection中科院强磁场科学中心
Affiliation1.Univ Sci & Technol China, Dept Chem, Hefei 230036, Anhui, Peoples R China
2.Chinese Acad Sci, High Field Magnet Lab, Mailbox 1110,350 Shushanhu Rd, Hefei 230031, Anhui, Peoples R China
3.CHMFL HCMTC Target Therapy Joint Lab, 350 Shushanhu Rd, Hefei 230031, Anhui, Peoples R China
4.Univ Sci & Technol China, Hefei 230036, Anhui, Peoples R China
5.Peking Univ, Hlth Sci Ctr, Inst Syst Biomed, Dept Biophys,Beijing Key Lab Tumor Syst Biol, Beijing 100191, Peoples R China
6.Peking Univ, Hlth Sci Ctr, Sch Basic Med Sci, Ctr Mol & Translat Med, Beijing 100191, Peoples R China
7.Chinese Acad Sci, Inst Technol Innovat, Precis Targeted Therapy Discovery Ctr, Hefei Inst Phys Sci, Hefei 230088, Anhui, Peoples R China
8.Hefei Cosource Med Technol Co LTD, 358 Ganquan Rd, Hefei 230031, Anhui, Peoples R China
First Author AffilicationChinese Acad Sci, High Field Magnet Lab,Hefei 230031, Anhui, Peoples R China
Recommended Citation
GB/T 7714
Liang, Qianmao,Chen, Yongfei,Yu, Kailin,et al. Discovery of N-(3-(5-((3-acrylamido-4-(morpholine-4-carbonyl) phenyl)amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-methylphenyl)-4-(tert-butyl)benzamide (CHMFL-BTK-01) as a highly selective irreversible Bruton's tyrosine kinase (BTK) inhibitor[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2017,131:107-125.
APA Liang, Qianmao.,Chen, Yongfei.,Yu, Kailin.,Chen, Cheng.,Zhang, Shouxiang.,...&Liu, Jing.(2017).Discovery of N-(3-(5-((3-acrylamido-4-(morpholine-4-carbonyl) phenyl)amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-methylphenyl)-4-(tert-butyl)benzamide (CHMFL-BTK-01) as a highly selective irreversible Bruton's tyrosine kinase (BTK) inhibitor.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,131,107-125.
MLA Liang, Qianmao,et al."Discovery of N-(3-(5-((3-acrylamido-4-(morpholine-4-carbonyl) phenyl)amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-methylphenyl)-4-(tert-butyl)benzamide (CHMFL-BTK-01) as a highly selective irreversible Bruton's tyrosine kinase (BTK) inhibitor".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 131(2017):107-125.
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