Design, synthesis and biological evaluation of di-substituted cinnamic hydroxamic acids bearing urea/thiourea unit as potent histone deacetylase inhibitors
[Display omitted] A novel class of di-substituted cinnamic hydroxamic acid derivatives containing urea or thiourea unit was designed, synthesized and evaluated as HDAC inhibitors. All tested compounds demonstrated significant HDAC inhibitory activities and anti-proliferative effects against diverse...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2013-12, Vol.23 (23), p.6432-6435 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Ning, Chengqing Bi, Yanjing He, Yujun Huang, WenYuan Liu, Lifei Li, Yi Zhang, Sihan Liu, Xiaoyu Yu, Niefang |
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A novel class of di-substituted cinnamic hydroxamic acid derivatives containing urea or thiourea unit was designed, synthesized and evaluated as HDAC inhibitors. All tested compounds demonstrated significant HDAC inhibitory activities and anti-proliferative effects against diverse human tumor cell lines. Among them, 7l exhibited most potent pan-HDAC inhibitory activity, with an IC50 value of 130nM. It also showed strong cellular inhibition against diverse cell lines including HCT-116, MCF-7, MDB-MB-435 and NCI-460, with GI50 values of 0.35, 0.22, 0.51 and 0.48μM, respectively. |
| doi_str_mv | 10.1016/j.bmcl.2013.09.051 |
| format | Article |
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A novel class of di-substituted cinnamic hydroxamic acid derivatives containing urea or thiourea unit was designed, synthesized and evaluated as HDAC inhibitors. All tested compounds demonstrated significant HDAC inhibitory activities and anti-proliferative effects against diverse human tumor cell lines. Among them, 7l exhibited most potent pan-HDAC inhibitory activity, with an IC50 value of 130nM. It also showed strong cellular inhibition against diverse cell lines including HCT-116, MCF-7, MDB-MB-435 and NCI-460, with GI50 values of 0.35, 0.22, 0.51 and 0.48μM, respectively.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2013.09.051</identifier><identifier>PMID: 24119555</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Cell Line, Tumor ; Cell Proliferation - drug effects ; chemistry ; Cinnamates - chemical synthesis ; Cinnamates - chemistry ; Cinnamates - pharmacology ; Cinnamic hydroxamaic acid ; Drug Design ; Drug Screening Assays, Antitumor ; HCT116 Cells ; HDAC ; Histone deacetylase ; Histone Deacetylase Inhibitors - chemical synthesis ; Histone Deacetylase Inhibitors - chemistry ; Histone Deacetylase Inhibitors - pharmacology ; Humans ; hydroxamic acids ; Hydroxamic Acids - chemical synthesis ; Hydroxamic Acids - chemistry ; Hydroxamic Acids - pharmacology ; inhibitory concentration 50 ; MCF-7 Cells ; Models, Molecular ; Structure-Activity Relationship ; Thiourea ; Thiourea - analogs & derivatives ; Thiourea - chemistry ; Thiourea - pharmacology ; Urea ; Urea - analogs & derivatives ; Urea - chemistry ; Urea - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry letters, 2013-12, Vol.23 (23), p.6432-6435</ispartof><rights>2013 Elsevier Ltd</rights><rights>Copyright © 2013 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c413t-39f6bba20bca5e3771ac09c64ebd5cdb00cdef01fec930b3e3491ac56b35da993</citedby><cites>FETCH-LOGICAL-c413t-39f6bba20bca5e3771ac09c64ebd5cdb00cdef01fec930b3e3491ac56b35da993</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.2013.09.051$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24119555$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ning, Chengqing</creatorcontrib><creatorcontrib>Bi, Yanjing</creatorcontrib><creatorcontrib>He, Yujun</creatorcontrib><creatorcontrib>Huang, WenYuan</creatorcontrib><creatorcontrib>Liu, Lifei</creatorcontrib><creatorcontrib>Li, Yi</creatorcontrib><creatorcontrib>Zhang, Sihan</creatorcontrib><creatorcontrib>Liu, Xiaoyu</creatorcontrib><creatorcontrib>Yu, Niefang</creatorcontrib><title>Design, synthesis and biological evaluation of di-substituted cinnamic hydroxamic acids bearing urea/thiourea unit as potent histone deacetylase inhibitors</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
A novel class of di-substituted cinnamic hydroxamic acid derivatives containing urea or thiourea unit was designed, synthesized and evaluated as HDAC inhibitors. All tested compounds demonstrated significant HDAC inhibitory activities and anti-proliferative effects against diverse human tumor cell lines. Among them, 7l exhibited most potent pan-HDAC inhibitory activity, with an IC50 value of 130nM. It also showed strong cellular inhibition against diverse cell lines including HCT-116, MCF-7, MDB-MB-435 and NCI-460, with GI50 values of 0.35, 0.22, 0.51 and 0.48μM, respectively.</description><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>chemistry</subject><subject>Cinnamates - chemical synthesis</subject><subject>Cinnamates - chemistry</subject><subject>Cinnamates - pharmacology</subject><subject>Cinnamic hydroxamaic acid</subject><subject>Drug Design</subject><subject>Drug Screening Assays, Antitumor</subject><subject>HCT116 Cells</subject><subject>HDAC</subject><subject>Histone deacetylase</subject><subject>Histone Deacetylase Inhibitors - chemical synthesis</subject><subject>Histone Deacetylase Inhibitors - chemistry</subject><subject>Histone Deacetylase Inhibitors - pharmacology</subject><subject>Humans</subject><subject>hydroxamic acids</subject><subject>Hydroxamic Acids - chemical synthesis</subject><subject>Hydroxamic Acids - chemistry</subject><subject>Hydroxamic Acids - pharmacology</subject><subject>inhibitory concentration 50</subject><subject>MCF-7 Cells</subject><subject>Models, Molecular</subject><subject>Structure-Activity Relationship</subject><subject>Thiourea</subject><subject>Thiourea - analogs & derivatives</subject><subject>Thiourea - chemistry</subject><subject>Thiourea - pharmacology</subject><subject>Urea</subject><subject>Urea - analogs & derivatives</subject><subject>Urea - chemistry</subject><subject>Urea - pharmacology</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU1vEzEQhlcIREvhD3AAHzmw6Xhtb2KJS1U-pUocoBI3yx-zyUQbO9jeivwW_iwbUjjCye_hmdejeZrmOYcFB95fbhdu58dFB1wsQC9A8QfNOZe9bIUE9bA5B91Du9Ly21nzpJQtAJcg5ePmrJOca6XUefPzLRZax9esHGLdzLkwGwNzlMa0Jm9Hhnd2nGylFFkaWKC2TK5UqlPFwDzFaHfk2eYQcvrxO1pPoTCHNlNcsymjvawbSsfApkiV2cL2qWKsbEOlpogsoPVYD6MtyChuyFFNuTxtHg12LPjs_r1obt-_-3r9sb35_OHT9dVN6yUXtRV66J2zHThvFYrlklsP2vcSXVA-OAAfcAA-oNcCnEAh9Yyo3gkVrNbionl16t3n9H3CUs2OisdxtBHTVAxXAMsl9D3_PyrlqoPVCpYz2p1Qn1MpGQezz7Sz-WA4mKM_szVHf-boz4A2s7956MV9_-R2GP6O_BE2Ay9PwGCTsetMxdx-mRvmFbnoenX8982JwPlkd4TZFE8YPQbK6KsJif61wS_RkLoC</recordid><startdate>20131201</startdate><enddate>20131201</enddate><creator>Ning, Chengqing</creator><creator>Bi, Yanjing</creator><creator>He, Yujun</creator><creator>Huang, WenYuan</creator><creator>Liu, Lifei</creator><creator>Li, Yi</creator><creator>Zhang, Sihan</creator><creator>Liu, Xiaoyu</creator><creator>Yu, Niefang</creator><general>Elsevier Ltd</general><scope>FBQ</scope><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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20131201</creationdate><title>Design, synthesis and biological evaluation of di-substituted cinnamic hydroxamic acids bearing urea/thiourea unit as potent histone deacetylase inhibitors</title><author>Ning, Chengqing ; Bi, Yanjing ; He, Yujun ; Huang, WenYuan ; Liu, Lifei ; Li, Yi ; Zhang, Sihan ; Liu, Xiaoyu ; Yu, Niefang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c413t-39f6bba20bca5e3771ac09c64ebd5cdb00cdef01fec930b3e3491ac56b35da993</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>chemistry</topic><topic>Cinnamates - chemical synthesis</topic><topic>Cinnamates - chemistry</topic><topic>Cinnamates - pharmacology</topic><topic>Cinnamic hydroxamaic acid</topic><topic>Drug Design</topic><topic>Drug Screening Assays, Antitumor</topic><topic>HCT116 Cells</topic><topic>HDAC</topic><topic>Histone deacetylase</topic><topic>Histone Deacetylase Inhibitors - chemical synthesis</topic><topic>Histone Deacetylase Inhibitors - chemistry</topic><topic>Histone Deacetylase Inhibitors - pharmacology</topic><topic>Humans</topic><topic>hydroxamic acids</topic><topic>Hydroxamic Acids - chemical synthesis</topic><topic>Hydroxamic Acids - chemistry</topic><topic>Hydroxamic Acids - pharmacology</topic><topic>inhibitory concentration 50</topic><topic>MCF-7 Cells</topic><topic>Models, Molecular</topic><topic>Structure-Activity Relationship</topic><topic>Thiourea</topic><topic>Thiourea - analogs & derivatives</topic><topic>Thiourea - chemistry</topic><topic>Thiourea - pharmacology</topic><topic>Urea</topic><topic>Urea - analogs & derivatives</topic><topic>Urea - chemistry</topic><topic>Urea - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ning, Chengqing</creatorcontrib><creatorcontrib>Bi, Yanjing</creatorcontrib><creatorcontrib>He, Yujun</creatorcontrib><creatorcontrib>Huang, WenYuan</creatorcontrib><creatorcontrib>Liu, Lifei</creatorcontrib><creatorcontrib>Li, Yi</creatorcontrib><creatorcontrib>Zhang, Sihan</creatorcontrib><creatorcontrib>Liu, Xiaoyu</creatorcontrib><creatorcontrib>Yu, Niefang</creatorcontrib><collection>AGRIS</collection><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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ning, Chengqing</au><au>Bi, Yanjing</au><au>He, Yujun</au><au>Huang, WenYuan</au><au>Liu, Lifei</au><au>Li, Yi</au><au>Zhang, Sihan</au><au>Liu, Xiaoyu</au><au>Yu, Niefang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis and biological evaluation of di-substituted cinnamic hydroxamic acids bearing urea/thiourea unit as potent histone deacetylase inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2013-12-01</date><risdate>2013</risdate><volume>23</volume><issue>23</issue><spage>6432</spage><epage>6435</epage><pages>6432-6435</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
A novel class of di-substituted cinnamic hydroxamic acid derivatives containing urea or thiourea unit was designed, synthesized and evaluated as HDAC inhibitors. All tested compounds demonstrated significant HDAC inhibitory activities and anti-proliferative effects against diverse human tumor cell lines. Among them, 7l exhibited most potent pan-HDAC inhibitory activity, with an IC50 value of 130nM. It also showed strong cellular inhibition against diverse cell lines including HCT-116, MCF-7, MDB-MB-435 and NCI-460, with GI50 values of 0.35, 0.22, 0.51 and 0.48μM, respectively.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>24119555</pmid><doi>10.1016/j.bmcl.2013.09.051</doi><tpages>4</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2013-12, Vol.23 (23), p.6432-6435 |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Cell Line, Tumor Cell Proliferation - drug effects chemistry Cinnamates - chemical synthesis Cinnamates - chemistry Cinnamates - pharmacology Cinnamic hydroxamaic acid Drug Design Drug Screening Assays, Antitumor HCT116 Cells HDAC Histone deacetylase Histone Deacetylase Inhibitors - chemical synthesis Histone Deacetylase Inhibitors - chemistry Histone Deacetylase Inhibitors - pharmacology Humans hydroxamic acids Hydroxamic Acids - chemical synthesis Hydroxamic Acids - chemistry Hydroxamic Acids - pharmacology inhibitory concentration 50 MCF-7 Cells Models, Molecular Structure-Activity Relationship Thiourea Thiourea - analogs & derivatives Thiourea - chemistry Thiourea - pharmacology Urea Urea - analogs & derivatives Urea - chemistry Urea - pharmacology |
| title | Design, synthesis and biological evaluation of di-substituted cinnamic hydroxamic acids bearing urea/thiourea unit as potent histone deacetylase inhibitors |
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