Synthesis, biological evaluation and structure–activity relationship studies of isoflavene based Mannich bases with potent anti-cancer activity
[Display omitted] Phenoxodiol, an analogue of the isoflavone natural product daidzein, is a potent anti-cancer agent that has been investigated for the treatment of hormone dependent cancers. This molecular scaffold was reacted with different primary amines and secondary amines under different Manni...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2015-11, Vol.25 (22), p.5377-5383 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Chen, Yilin Cass, Shelley L. Kutty, Samuel K. Yee, Eugene M.H. Chan, Daniel S.H. Gardner, Christopher R. Vittorio, Orazio Pasquier, Eddy Black, David StC Kumar, Naresh |
| description | [Display omitted]
Phenoxodiol, an analogue of the isoflavone natural product daidzein, is a potent anti-cancer agent that has been investigated for the treatment of hormone dependent cancers. This molecular scaffold was reacted with different primary amines and secondary amines under different Mannich conditions to yield either benzoxazine or aminomethyl substituted analogues. These processes enabled the generation of a diverse range of analogues that were required for structure–activity relationship (SAR) studies. The resulting Mannich bases exhibited prominent anti-proliferative effects against SHEP neuroblastoma and MDA-MB-231 breast adenocarcinoma cell lines. Further cytotoxicity studies against MRC-5 normal lung fibroblast cells showed that the isoflavene analogues were selective towards cancer cells. |
| doi_str_mv | 10.1016/j.bmcl.2015.09.027 |
| format | Article |
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Phenoxodiol, an analogue of the isoflavone natural product daidzein, is a potent anti-cancer agent that has been investigated for the treatment of hormone dependent cancers. This molecular scaffold was reacted with different primary amines and secondary amines under different Mannich conditions to yield either benzoxazine or aminomethyl substituted analogues. These processes enabled the generation of a diverse range of analogues that were required for structure–activity relationship (SAR) studies. The resulting Mannich bases exhibited prominent anti-proliferative effects against SHEP neuroblastoma and MDA-MB-231 breast adenocarcinoma cell lines. Further cytotoxicity studies against MRC-5 normal lung fibroblast cells showed that the isoflavene analogues were selective towards cancer cells.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2015.09.027</identifier><identifier>PMID: 26432036</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Anti-cancer ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Antineoplastic Agents - toxicity ; Benzoxazine ; Breast Neoplasms - drug therapy ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Cell Survival - drug effects ; Drug Screening Assays, Antitumor ; Female ; Fibroblasts - cytology ; Fibroblasts - drug effects ; Humans ; Inhibitory Concentration 50 ; Isoflavene ; Isoflavones - chemical synthesis ; Isoflavones - chemistry ; Isoflavones - toxicity ; Mannich base ; Mannich Bases - chemical synthesis ; Mannich Bases - chemistry ; Mannich Bases - pharmacology ; Mannich Bases - toxicity ; Molecular Structure ; Phenoxodiol ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2015-11, Vol.25 (22), p.5377-5383</ispartof><rights>2015 Elsevier Ltd</rights><rights>Copyright © 2015 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-f716507084fa13cba79e21dd0766cdbe10ebfa4615116e9fd5dad9527f27831e3</citedby><cites>FETCH-LOGICAL-c356t-f716507084fa13cba79e21dd0766cdbe10ebfa4615116e9fd5dad9527f27831e3</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.2015.09.027$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26432036$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Yilin</creatorcontrib><creatorcontrib>Cass, Shelley L.</creatorcontrib><creatorcontrib>Kutty, Samuel K.</creatorcontrib><creatorcontrib>Yee, Eugene M.H.</creatorcontrib><creatorcontrib>Chan, Daniel S.H.</creatorcontrib><creatorcontrib>Gardner, Christopher R.</creatorcontrib><creatorcontrib>Vittorio, Orazio</creatorcontrib><creatorcontrib>Pasquier, Eddy</creatorcontrib><creatorcontrib>Black, David StC</creatorcontrib><creatorcontrib>Kumar, Naresh</creatorcontrib><title>Synthesis, biological evaluation and structure–activity relationship studies of isoflavene based Mannich bases with potent anti-cancer activity</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
Phenoxodiol, an analogue of the isoflavone natural product daidzein, is a potent anti-cancer agent that has been investigated for the treatment of hormone dependent cancers. This molecular scaffold was reacted with different primary amines and secondary amines under different Mannich conditions to yield either benzoxazine or aminomethyl substituted analogues. These processes enabled the generation of a diverse range of analogues that were required for structure–activity relationship (SAR) studies. The resulting Mannich bases exhibited prominent anti-proliferative effects against SHEP neuroblastoma and MDA-MB-231 breast adenocarcinoma cell lines. Further cytotoxicity studies against MRC-5 normal lung fibroblast cells showed that the isoflavene analogues were selective towards cancer cells.</description><subject>Anti-cancer</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antineoplastic Agents - toxicity</subject><subject>Benzoxazine</subject><subject>Breast Neoplasms - drug therapy</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Cell Survival - drug effects</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Female</subject><subject>Fibroblasts - cytology</subject><subject>Fibroblasts - drug effects</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Isoflavene</subject><subject>Isoflavones - chemical synthesis</subject><subject>Isoflavones - chemistry</subject><subject>Isoflavones - toxicity</subject><subject>Mannich base</subject><subject>Mannich Bases - chemical synthesis</subject><subject>Mannich Bases - chemistry</subject><subject>Mannich Bases - pharmacology</subject><subject>Mannich Bases - toxicity</subject><subject>Molecular Structure</subject><subject>Phenoxodiol</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc-KFDEQh4Mo7jj6Ah4kRw92m6TT6W7wIsv6B1Y8qOAtpJOKU0OmMybpkbn5CuIb-iT27Ox69FQUfPVB_X6EPOWs5oyrl9t63NlQC8bbmg01E909suJSyaqRrL1PVmxQrOoH-fWCPMp5yxiXTMqH5EIo2QjWqBX59ek4lQ1kzC_oiDHEb2hNoHAwYTYF40TN5GguabZlTvDn529jCx6wHGmCcEPkDe4XYnYImUZPMUcfzAEmoKPJ4OgHM01oNzdbpj-wbOg-FpjK4i5YWTNZSPTO-5g88CZkeHI71-TLm6vPl--q649v31--vq5s06pS-Y6rlnWsl97wxo6mG0Bw51inlHUjcAajN1LxlnMFg3etM25oRedF1zccmjV5fvbuU_w-Qy56h9lCCGaCOGfNO9Er1fdLVGsizqhNMecEXu8T7kw6as70qQq91acq9KkKzQa9VLEcPbv1z-MO3L-Tu-wX4NUZgOXLA0LS2SIsWThMYIt2Ef_n_wtSgp_D</recordid><startdate>20151115</startdate><enddate>20151115</enddate><creator>Chen, Yilin</creator><creator>Cass, Shelley L.</creator><creator>Kutty, Samuel K.</creator><creator>Yee, Eugene M.H.</creator><creator>Chan, Daniel S.H.</creator><creator>Gardner, Christopher R.</creator><creator>Vittorio, Orazio</creator><creator>Pasquier, Eddy</creator><creator>Black, David StC</creator><creator>Kumar, Naresh</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>20151115</creationdate><title>Synthesis, biological evaluation and structure–activity relationship studies of isoflavene based Mannich bases with potent anti-cancer activity</title><author>Chen, Yilin ; Cass, Shelley L. ; Kutty, Samuel K. ; Yee, Eugene M.H. ; Chan, Daniel S.H. ; Gardner, Christopher R. ; Vittorio, Orazio ; Pasquier, Eddy ; Black, David StC ; Kumar, Naresh</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-f716507084fa13cba79e21dd0766cdbe10ebfa4615116e9fd5dad9527f27831e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Anti-cancer</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antineoplastic Agents - toxicity</topic><topic>Benzoxazine</topic><topic>Breast Neoplasms - drug therapy</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Cell Survival - drug effects</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Female</topic><topic>Fibroblasts - cytology</topic><topic>Fibroblasts - drug effects</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Isoflavene</topic><topic>Isoflavones - chemical synthesis</topic><topic>Isoflavones - chemistry</topic><topic>Isoflavones - toxicity</topic><topic>Mannich base</topic><topic>Mannich Bases - chemical synthesis</topic><topic>Mannich Bases - chemistry</topic><topic>Mannich Bases - pharmacology</topic><topic>Mannich Bases - toxicity</topic><topic>Molecular Structure</topic><topic>Phenoxodiol</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Yilin</creatorcontrib><creatorcontrib>Cass, Shelley L.</creatorcontrib><creatorcontrib>Kutty, Samuel K.</creatorcontrib><creatorcontrib>Yee, Eugene M.H.</creatorcontrib><creatorcontrib>Chan, Daniel S.H.</creatorcontrib><creatorcontrib>Gardner, Christopher R.</creatorcontrib><creatorcontrib>Vittorio, Orazio</creatorcontrib><creatorcontrib>Pasquier, Eddy</creatorcontrib><creatorcontrib>Black, David StC</creatorcontrib><creatorcontrib>Kumar, Naresh</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>Chen, Yilin</au><au>Cass, Shelley L.</au><au>Kutty, Samuel K.</au><au>Yee, Eugene M.H.</au><au>Chan, Daniel S.H.</au><au>Gardner, Christopher R.</au><au>Vittorio, Orazio</au><au>Pasquier, Eddy</au><au>Black, David StC</au><au>Kumar, Naresh</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, biological evaluation and structure–activity relationship studies of isoflavene based Mannich bases with potent anti-cancer activity</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2015-11-15</date><risdate>2015</risdate><volume>25</volume><issue>22</issue><spage>5377</spage><epage>5383</epage><pages>5377-5383</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
Phenoxodiol, an analogue of the isoflavone natural product daidzein, is a potent anti-cancer agent that has been investigated for the treatment of hormone dependent cancers. This molecular scaffold was reacted with different primary amines and secondary amines under different Mannich conditions to yield either benzoxazine or aminomethyl substituted analogues. These processes enabled the generation of a diverse range of analogues that were required for structure–activity relationship (SAR) studies. The resulting Mannich bases exhibited prominent anti-proliferative effects against SHEP neuroblastoma and MDA-MB-231 breast adenocarcinoma cell lines. Further cytotoxicity studies against MRC-5 normal lung fibroblast cells showed that the isoflavene analogues were selective towards cancer cells.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>26432036</pmid><doi>10.1016/j.bmcl.2015.09.027</doi><tpages>7</tpages></addata></record> |
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| subjects | Anti-cancer Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antineoplastic Agents - toxicity Benzoxazine Breast Neoplasms - drug therapy Cell Line, Tumor Cell Proliferation - drug effects Cell Survival - drug effects Drug Screening Assays, Antitumor Female Fibroblasts - cytology Fibroblasts - drug effects Humans Inhibitory Concentration 50 Isoflavene Isoflavones - chemical synthesis Isoflavones - chemistry Isoflavones - toxicity Mannich base Mannich Bases - chemical synthesis Mannich Bases - chemistry Mannich Bases - pharmacology Mannich Bases - toxicity Molecular Structure Phenoxodiol Structure-Activity Relationship |
| title | Synthesis, biological evaluation and structure–activity relationship studies of isoflavene based Mannich bases with potent anti-cancer activity |
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