Discovery of novel pyrrolo[2,3-b]pyridine derivatives bearing 4-oxoquinoline moiety as potential antitumor inhibitor
[Display omitted] A series of pyrrolo[2,3-b]pyridine derivatives bearing 4-oxoquinoline moiety were designed, synthesized and evaluated for the anti-proliferative on three cancer cell lines (A549, HepG2 and MCF-7) in vitro. Most of the compounds showed moderate to high potency. Some excellent compou...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2020-01, Vol.30 (2), p.126848-126848, Article 126848 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Liu, Huimin Duan, Yongli Xiong, Hehua Zhang, Jianqing Huang, Shunmin Chen, Ting Zheng, Pengwu Tang, Qidong |
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A series of pyrrolo[2,3-b]pyridine derivatives bearing 4-oxoquinoline moiety were designed, synthesized and evaluated for the anti-proliferative on three cancer cell lines (A549, HepG2 and MCF-7) in vitro. Most of the compounds showed moderate to high potency. Some excellent compounds were tested for the inhibitory activity of c-Met kinase. Compound 34 (c-Met IC50 = 17 nM) was investigated the selectivity against Flt-3, c-Kit, VEGFR-2, ALK, PDGFR-β and RON. Structure-activity relationship studies indicated that hydrogen, fluorine atom, and mono-electron-withdrawing groups (mono-EWGs, such as R2 = F) on R, R1 and R2, respectively, were beneficial for the anti-proliferative activities of the target compounds. Besides, we have took further study on the combined mode between compound 34 and c-Met kinase through molecular docking. |
| doi_str_mv | 10.1016/j.bmcl.2019.126848 |
| format | Article |
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A series of pyrrolo[2,3-b]pyridine derivatives bearing 4-oxoquinoline moiety were designed, synthesized and evaluated for the anti-proliferative on three cancer cell lines (A549, HepG2 and MCF-7) in vitro. Most of the compounds showed moderate to high potency. Some excellent compounds were tested for the inhibitory activity of c-Met kinase. Compound 34 (c-Met IC50 = 17 nM) was investigated the selectivity against Flt-3, c-Kit, VEGFR-2, ALK, PDGFR-β and RON. Structure-activity relationship studies indicated that hydrogen, fluorine atom, and mono-electron-withdrawing groups (mono-EWGs, such as R2 = F) on R, R1 and R2, respectively, were beneficial for the anti-proliferative activities of the target compounds. Besides, we have took further study on the combined mode between compound 34 and c-Met kinase through molecular docking.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2019.126848</identifier><identifier>PMID: 31836443</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>4-Oxoquinoline ; 4-Quinolones - chemical synthesis ; 4-Quinolones - chemistry ; Anti-proliferative activity ; Antineoplastic Agents - pharmacology ; Antineoplastic Agents - therapeutic use ; c-Met ; Humans ; Molecular Structure ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Pyrrolo[2,3-b]pyridine derivatives ; Structure-Activity Relationship ; Synthesis</subject><ispartof>Bioorganic & medicinal chemistry letters, 2020-01, Vol.30 (2), p.126848-126848, Article 126848</ispartof><rights>2019 Elsevier Ltd</rights><rights>Copyright © 2019 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-3262003f512fce1e4cf81b6d2de50370408f8f9f7dd1f624e421bc4ff1f7c2323</citedby><cites>FETCH-LOGICAL-c356t-3262003f512fce1e4cf81b6d2de50370408f8f9f7dd1f624e421bc4ff1f7c2323</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2019.126848$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,778,782,3539,27907,27908,45978</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31836443$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Huimin</creatorcontrib><creatorcontrib>Duan, Yongli</creatorcontrib><creatorcontrib>Xiong, Hehua</creatorcontrib><creatorcontrib>Zhang, Jianqing</creatorcontrib><creatorcontrib>Huang, Shunmin</creatorcontrib><creatorcontrib>Chen, Ting</creatorcontrib><creatorcontrib>Zheng, Pengwu</creatorcontrib><creatorcontrib>Tang, Qidong</creatorcontrib><title>Discovery of novel pyrrolo[2,3-b]pyridine derivatives bearing 4-oxoquinoline moiety as potential antitumor inhibitor</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
A series of pyrrolo[2,3-b]pyridine derivatives bearing 4-oxoquinoline moiety were designed, synthesized and evaluated for the anti-proliferative on three cancer cell lines (A549, HepG2 and MCF-7) in vitro. Most of the compounds showed moderate to high potency. Some excellent compounds were tested for the inhibitory activity of c-Met kinase. Compound 34 (c-Met IC50 = 17 nM) was investigated the selectivity against Flt-3, c-Kit, VEGFR-2, ALK, PDGFR-β and RON. Structure-activity relationship studies indicated that hydrogen, fluorine atom, and mono-electron-withdrawing groups (mono-EWGs, such as R2 = F) on R, R1 and R2, respectively, were beneficial for the anti-proliferative activities of the target compounds. Besides, we have took further study on the combined mode between compound 34 and c-Met kinase through molecular docking.</description><subject>4-Oxoquinoline</subject><subject>4-Quinolones - chemical synthesis</subject><subject>4-Quinolones - chemistry</subject><subject>Anti-proliferative activity</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antineoplastic Agents - therapeutic use</subject><subject>c-Met</subject><subject>Humans</subject><subject>Molecular Structure</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Pyrrolo[2,3-b]pyridine derivatives</subject><subject>Structure-Activity Relationship</subject><subject>Synthesis</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1rGzEQhkVoSdykf6CHomMPXUcfY3kNvZQ0bQOBXhIIhCJ2pVE7ZnflSrKJ_31knPbY08zAMy8zD2PvpJhLIc3let6PbpgrIVdzqUwL7QmbSTDQaBCLV2wmVkY07QoeztibnNdCSBAAp-xMy1YbAD1j5QtlF3eY9jwGPtVu4Jt9SnGIj-qjbvqfdSJPE3KPiXZdoR1m3mOXaPrFoYlP8c-WpjgckDESlj3vMt_EglOhbuBdLWU7xsRp-k09lZgu2OvQDRnfvtRzdv_1-u7qe3P749vN1efbxumFKY1WRgmhw0Kq4FAiuNDK3njlcSH0UoBoQxtWYem9DEYBgpK9gxBkWDqllT5nH465m1SPxFzsWL_FYegmjNtsldbaSKnBVFQdUZdizgmD3SQau7S3UtiDbbu2B9v2YNsebdel9y_5235E_2_lr94KfDoCWL_cESabHeHk0FNCV6yP9L_8Z87JkvQ</recordid><startdate>20200115</startdate><enddate>20200115</enddate><creator>Liu, Huimin</creator><creator>Duan, Yongli</creator><creator>Xiong, Hehua</creator><creator>Zhang, Jianqing</creator><creator>Huang, Shunmin</creator><creator>Chen, Ting</creator><creator>Zheng, Pengwu</creator><creator>Tang, Qidong</creator><general>Elsevier Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20200115</creationdate><title>Discovery of novel pyrrolo[2,3-b]pyridine derivatives bearing 4-oxoquinoline moiety as potential antitumor inhibitor</title><author>Liu, Huimin ; Duan, Yongli ; Xiong, Hehua ; Zhang, Jianqing ; Huang, Shunmin ; Chen, Ting ; Zheng, Pengwu ; Tang, Qidong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-3262003f512fce1e4cf81b6d2de50370408f8f9f7dd1f624e421bc4ff1f7c2323</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>4-Oxoquinoline</topic><topic>4-Quinolones - chemical synthesis</topic><topic>4-Quinolones - chemistry</topic><topic>Anti-proliferative activity</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antineoplastic Agents - therapeutic use</topic><topic>c-Met</topic><topic>Humans</topic><topic>Molecular Structure</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><topic>Pyrrolo[2,3-b]pyridine derivatives</topic><topic>Structure-Activity Relationship</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Huimin</creatorcontrib><creatorcontrib>Duan, Yongli</creatorcontrib><creatorcontrib>Xiong, Hehua</creatorcontrib><creatorcontrib>Zhang, Jianqing</creatorcontrib><creatorcontrib>Huang, Shunmin</creatorcontrib><creatorcontrib>Chen, Ting</creatorcontrib><creatorcontrib>Zheng, Pengwu</creatorcontrib><creatorcontrib>Tang, Qidong</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Huimin</au><au>Duan, Yongli</au><au>Xiong, Hehua</au><au>Zhang, Jianqing</au><au>Huang, Shunmin</au><au>Chen, Ting</au><au>Zheng, Pengwu</au><au>Tang, Qidong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of novel pyrrolo[2,3-b]pyridine derivatives bearing 4-oxoquinoline moiety as potential antitumor inhibitor</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2020-01-15</date><risdate>2020</risdate><volume>30</volume><issue>2</issue><spage>126848</spage><epage>126848</epage><pages>126848-126848</pages><artnum>126848</artnum><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
A series of pyrrolo[2,3-b]pyridine derivatives bearing 4-oxoquinoline moiety were designed, synthesized and evaluated for the anti-proliferative on three cancer cell lines (A549, HepG2 and MCF-7) in vitro. Most of the compounds showed moderate to high potency. Some excellent compounds were tested for the inhibitory activity of c-Met kinase. Compound 34 (c-Met IC50 = 17 nM) was investigated the selectivity against Flt-3, c-Kit, VEGFR-2, ALK, PDGFR-β and RON. Structure-activity relationship studies indicated that hydrogen, fluorine atom, and mono-electron-withdrawing groups (mono-EWGs, such as R2 = F) on R, R1 and R2, respectively, were beneficial for the anti-proliferative activities of the target compounds. Besides, we have took further study on the combined mode between compound 34 and c-Met kinase through molecular docking.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>31836443</pmid><doi>10.1016/j.bmcl.2019.126848</doi><tpages>1</tpages></addata></record> |
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| subjects | 4-Oxoquinoline 4-Quinolones - chemical synthesis 4-Quinolones - chemistry Anti-proliferative activity Antineoplastic Agents - pharmacology Antineoplastic Agents - therapeutic use c-Met Humans Molecular Structure Pyridines - chemical synthesis Pyridines - chemistry Pyrrolo[2,3-b]pyridine derivatives Structure-Activity Relationship Synthesis |
| title | Discovery of novel pyrrolo[2,3-b]pyridine derivatives bearing 4-oxoquinoline moiety as potential antitumor inhibitor |
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