1,2,3-Triazole analogs of combretastatin A-4 as potential microtubule-binding agents
A series of cis-restricted 1,4- and 1,5-disubstituted 1,2,3-triazole analogs of combretastatin A-4 (1) have been prepared. Cytotoxicity and tubulin inhibition studies showed that 2-methoxy-5-((5-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-1-yl)methyl)aniline (5e) and 2-methoxy-5-(1-(3,4,5-trimethoxybe...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2010-09, Vol.18 (18), p.6874-6885 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Odlo, Kristin Fournier-Dit-Chabert, Jérémie Ducki, Sylvie Gani, Osman A.B.S.M. Sylte, Ingebrigt Hansen, Trond Vidar |
| description | A series of cis-restricted 1,4- and 1,5-disubstituted 1,2,3-triazole analogs of combretastatin A-4 (1) have been prepared. Cytotoxicity and tubulin inhibition studies showed that 2-methoxy-5-((5-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-1-yl)methyl)aniline (5e) and 2-methoxy-5-(1-(3,4,5-trimethoxybenzyl)-1H-1,2,3-triazol-5-yl)aniline (6e) were two of the most active compounds. Molecular modeling studies revealed that the N-2 and N-3 atoms in the triazole rings in 5e and 6e did not form hydrogen bonds with the amino acids in the anticipated pharmacophore. |
| doi_str_mv | 10.1016/j.bmc.2010.07.032 |
| format | Article |
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Cytotoxicity and tubulin inhibition studies showed that 2-methoxy-5-((5-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-1-yl)methyl)aniline (5e) and 2-methoxy-5-(1-(3,4,5-trimethoxybenzyl)-1H-1,2,3-triazol-5-yl)aniline (6e) were two of the most active compounds. Molecular modeling studies revealed that the N-2 and N-3 atoms in the triazole rings in 5e and 6e did not form hydrogen bonds with the amino acids in the anticipated pharmacophore.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2010.07.032</identifier><identifier>PMID: 20708408</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>12,3-Triazoles ; Amino acids ; Aniline Compounds - chemical synthesis ; Aniline Compounds - chemistry ; Aniline Compounds - toxicity ; Antineoplastic agents ; Binding Sites ; Biological and medical sciences ; Cell Line, Tumor ; Combretastatin A-4 ; Computer Simulation ; Cytotoxic ; General aspects ; Humans ; Medical sciences ; Microtubules - chemistry ; Microtubules - metabolism ; Molecular Modeling ; Pharmacology. Drug treatments ; Protein Structure, Tertiary ; Stilbenes - chemical synthesis ; Stilbenes - chemistry ; Stilbenes - toxicity ; Triazoles - chemical synthesis ; Triazoles - chemistry ; Triazoles - toxicity ; Tubulin Modulators - chemical synthesis ; Tubulin Modulators - chemistry ; Tubulin Modulators - toxicity</subject><ispartof>Bioorganic & medicinal chemistry, 2010-09, Vol.18 (18), p.6874-6885</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright (c) 2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c446t-74f8b51977761c42abc71fff6cee1c3577ea66962708dccb24a168af89c40b3d3</citedby><cites>FETCH-LOGICAL-c446t-74f8b51977761c42abc71fff6cee1c3577ea66962708dccb24a168af89c40b3d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2010.07.032$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,782,786,3552,27931,27932,46002</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23248242$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20708408$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Odlo, Kristin</creatorcontrib><creatorcontrib>Fournier-Dit-Chabert, Jérémie</creatorcontrib><creatorcontrib>Ducki, Sylvie</creatorcontrib><creatorcontrib>Gani, Osman A.B.S.M.</creatorcontrib><creatorcontrib>Sylte, Ingebrigt</creatorcontrib><creatorcontrib>Hansen, Trond Vidar</creatorcontrib><title>1,2,3-Triazole analogs of combretastatin A-4 as potential microtubule-binding agents</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A series of cis-restricted 1,4- and 1,5-disubstituted 1,2,3-triazole analogs of combretastatin A-4 (1) have been prepared. Cytotoxicity and tubulin inhibition studies showed that 2-methoxy-5-((5-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-1-yl)methyl)aniline (5e) and 2-methoxy-5-(1-(3,4,5-trimethoxybenzyl)-1H-1,2,3-triazol-5-yl)aniline (6e) were two of the most active compounds. Molecular modeling studies revealed that the N-2 and N-3 atoms in the triazole rings in 5e and 6e did not form hydrogen bonds with the amino acids in the anticipated pharmacophore.</description><subject>12,3-Triazoles</subject><subject>Amino acids</subject><subject>Aniline Compounds - chemical synthesis</subject><subject>Aniline Compounds - chemistry</subject><subject>Aniline Compounds - toxicity</subject><subject>Antineoplastic agents</subject><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Combretastatin A-4</subject><subject>Computer Simulation</subject><subject>Cytotoxic</subject><subject>General aspects</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Microtubules - chemistry</subject><subject>Microtubules - metabolism</subject><subject>Molecular Modeling</subject><subject>Pharmacology. Drug treatments</subject><subject>Protein Structure, Tertiary</subject><subject>Stilbenes - chemical synthesis</subject><subject>Stilbenes - chemistry</subject><subject>Stilbenes - toxicity</subject><subject>Triazoles - chemical synthesis</subject><subject>Triazoles - chemistry</subject><subject>Triazoles - toxicity</subject><subject>Tubulin Modulators - chemical synthesis</subject><subject>Tubulin Modulators - chemistry</subject><subject>Tubulin Modulators - toxicity</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkU2LFDEQhoMo7rj6A7xIX8TL9pivzgeelsUvWPAynkOSrgwZujtjkhbcX2-GGfWmnoqinnop6kHoJcFbgol4e9i62W8pbj2WW8zoI7QhXPCeMU0eow3WQvVYaXGFnpVywBhTrslTdEWxxIpjtUE7ckNvWL_L0T6kCTq72CntS5dC59PsMlRbqq1x6W573tnSHVOFpUY7dXP0OdXVrRP0Li5jXPad3bdheY6eBDsVeHGp1-jrh_e7u0_9_ZePn-9u73vPuai95EG5gWgppSCeU-u8JCEE4QGIZ4OUYIXQgrZjR-8d5ZYIZYPSnmPHRnaN3pxzjzl9W6FUM8fiYZrsAmktRg980Bgz9V-kUlyyf5JyYFoLrmUjyZlsbyglQzDHHGebfxiCzcmPOZjmx5z8GCxN89N2Xl3SVzfD-Hvjl5AGvL4Atng7hWwXH8sfjlGuKD8FvTtz0P77PUI2xUdYPIwxg69mTPEvZ_wEim6rsg</recordid><startdate>20100915</startdate><enddate>20100915</enddate><creator>Odlo, Kristin</creator><creator>Fournier-Dit-Chabert, Jérémie</creator><creator>Ducki, Sylvie</creator><creator>Gani, Osman A.B.S.M.</creator><creator>Sylte, Ingebrigt</creator><creator>Hansen, Trond Vidar</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</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>20100915</creationdate><title>1,2,3-Triazole analogs of combretastatin A-4 as potential microtubule-binding agents</title><author>Odlo, Kristin ; Fournier-Dit-Chabert, Jérémie ; Ducki, Sylvie ; Gani, Osman A.B.S.M. ; Sylte, Ingebrigt ; Hansen, Trond Vidar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c446t-74f8b51977761c42abc71fff6cee1c3577ea66962708dccb24a168af89c40b3d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>12,3-Triazoles</topic><topic>Amino acids</topic><topic>Aniline Compounds - chemical synthesis</topic><topic>Aniline Compounds - chemistry</topic><topic>Aniline Compounds - toxicity</topic><topic>Antineoplastic agents</topic><topic>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Combretastatin A-4</topic><topic>Computer Simulation</topic><topic>Cytotoxic</topic><topic>General aspects</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Microtubules - chemistry</topic><topic>Microtubules - metabolism</topic><topic>Molecular Modeling</topic><topic>Pharmacology. 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Cytotoxicity and tubulin inhibition studies showed that 2-methoxy-5-((5-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-1-yl)methyl)aniline (5e) and 2-methoxy-5-(1-(3,4,5-trimethoxybenzyl)-1H-1,2,3-triazol-5-yl)aniline (6e) were two of the most active compounds. Molecular modeling studies revealed that the N-2 and N-3 atoms in the triazole rings in 5e and 6e did not form hydrogen bonds with the amino acids in the anticipated pharmacophore.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>20708408</pmid><doi>10.1016/j.bmc.2010.07.032</doi><tpages>12</tpages></addata></record> |
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| subjects | 12,3-Triazoles Amino acids Aniline Compounds - chemical synthesis Aniline Compounds - chemistry Aniline Compounds - toxicity Antineoplastic agents Binding Sites Biological and medical sciences Cell Line, Tumor Combretastatin A-4 Computer Simulation Cytotoxic General aspects Humans Medical sciences Microtubules - chemistry Microtubules - metabolism Molecular Modeling Pharmacology. Drug treatments Protein Structure, Tertiary Stilbenes - chemical synthesis Stilbenes - chemistry Stilbenes - toxicity Triazoles - chemical synthesis Triazoles - chemistry Triazoles - toxicity Tubulin Modulators - chemical synthesis Tubulin Modulators - chemistry Tubulin Modulators - toxicity |
| title | 1,2,3-Triazole analogs of combretastatin A-4 as potential microtubule-binding agents |
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