Synthesis and biological activity of desmethoxy analogues of coruscanone A
Desmethoxy analogues of coruscanone A were prepared via Ti( iPrO) 4 mediated condensation of cyclopentenedione with aldehydes. Antifungal activity of 2-benzylidenecyclopent-4-ene-1,3-dione was comparable to those of coruscanone A and fluconazole, and was superior to the drug standard against several...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2011-10, Vol.21 (20), p.6062-6066 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Tichotová, Lucie Matoušová, Eliška Špulák, Marcel Kuneš, Jiří Votruba, Ivan Buchta, Vladimír Pour, Milan |
| description | Desmethoxy analogues of coruscanone A were prepared via Ti(
iPrO)
4 mediated condensation of cyclopentenedione with aldehydes. Antifungal activity of 2-benzylidenecyclopent-4-ene-1,3-dione was comparable to those of coruscanone A and fluconazole, and was superior to the drug standard against several non-albicans
Candida species. Experiments on antiproliferative activity indicated lower cytotoxicity compared to the natural product.
A series of simple desmethoxy analogues of coruscanone A was prepared via a novel version of Ti(
iPrO)
4-mediated Knoevenagel condensation of cyclopentenedione with substituted benzaldehydes and cinnamic aldehydes, and the compounds were evaluated for antifungal activity and cytotoxicity. The most potent 2-benzylidenecyclopent-4-ene-1,3-dione possessed antifungal effect comparable to coruscanone A and a somewhat broader spectrum of activity against
Candida species. The compound was also superior to fluconazole against several non-albicans
Candida sp. Evaluation of the ability of the compound to influence cell proliferation using two different assays showed that 2-benzylidenecyclopent-4-ene-1,3-dione has lower cytotoxicity compared to the natural product. |
| doi_str_mv | 10.1016/j.bmcl.2011.08.059 |
| format | Article |
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iPrO)
4 mediated condensation of cyclopentenedione with aldehydes. Antifungal activity of 2-benzylidenecyclopent-4-ene-1,3-dione was comparable to those of coruscanone A and fluconazole, and was superior to the drug standard against several non-albicans
Candida species. Experiments on antiproliferative activity indicated lower cytotoxicity compared to the natural product.
A series of simple desmethoxy analogues of coruscanone A was prepared via a novel version of Ti(
iPrO)
4-mediated Knoevenagel condensation of cyclopentenedione with substituted benzaldehydes and cinnamic aldehydes, and the compounds were evaluated for antifungal activity and cytotoxicity. The most potent 2-benzylidenecyclopent-4-ene-1,3-dione possessed antifungal effect comparable to coruscanone A and a somewhat broader spectrum of activity against
Candida species. The compound was also superior to fluconazole against several non-albicans
Candida sp. Evaluation of the ability of the compound to influence cell proliferation using two different assays showed that 2-benzylidenecyclopent-4-ene-1,3-dione has lower cytotoxicity compared to the natural product.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2011.08.059</identifier><identifier>PMID: 21903391</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>4-Butyrolactone - analogs & derivatives ; 4-Butyrolactone - chemical synthesis ; 4-Butyrolactone - chemistry ; 4-Butyrolactone - pharmacology ; aldehydes ; Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antifungal ; Antifungal agents ; Antifungal Agents - chemical synthesis ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; antifungal properties ; Biological and medical sciences ; Candida ; Candida - drug effects ; Candidiasis - drug therapy ; Cell Line ; Cell Line, Tumor ; cell proliferation ; condensation ; Cyclopentanes - chemical synthesis ; Cyclopentanes - chemistry ; Cyclopentanes - pharmacology ; Cyclopentenediones ; Cytotoxicity ; fluconazole ; Humans ; Knoevenagel ; Lewis acid ; Medical sciences ; Mice ; Microbial Sensitivity Tests ; Pharmacology. Drug treatments ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2011-10, Vol.21 (20), p.6062-6066</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c441t-b63bfd57ed9af3d9a6e222a2fec97f693ded5d3ba19d3f34a55c9ce76138e6833</citedby><cites>FETCH-LOGICAL-c441t-b63bfd57ed9af3d9a6e222a2fec97f693ded5d3ba19d3f34a55c9ce76138e6833</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.2011.08.059$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24600339$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21903391$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tichotová, Lucie</creatorcontrib><creatorcontrib>Matoušová, Eliška</creatorcontrib><creatorcontrib>Špulák, Marcel</creatorcontrib><creatorcontrib>Kuneš, Jiří</creatorcontrib><creatorcontrib>Votruba, Ivan</creatorcontrib><creatorcontrib>Buchta, Vladimír</creatorcontrib><creatorcontrib>Pour, Milan</creatorcontrib><title>Synthesis and biological activity of desmethoxy analogues of coruscanone A</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Desmethoxy analogues of coruscanone A were prepared via Ti(
iPrO)
4 mediated condensation of cyclopentenedione with aldehydes. Antifungal activity of 2-benzylidenecyclopent-4-ene-1,3-dione was comparable to those of coruscanone A and fluconazole, and was superior to the drug standard against several non-albicans
Candida species. Experiments on antiproliferative activity indicated lower cytotoxicity compared to the natural product.
A series of simple desmethoxy analogues of coruscanone A was prepared via a novel version of Ti(
iPrO)
4-mediated Knoevenagel condensation of cyclopentenedione with substituted benzaldehydes and cinnamic aldehydes, and the compounds were evaluated for antifungal activity and cytotoxicity. The most potent 2-benzylidenecyclopent-4-ene-1,3-dione possessed antifungal effect comparable to coruscanone A and a somewhat broader spectrum of activity against
Candida species. The compound was also superior to fluconazole against several non-albicans
Candida sp. Evaluation of the ability of the compound to influence cell proliferation using two different assays showed that 2-benzylidenecyclopent-4-ene-1,3-dione has lower cytotoxicity compared to the natural product.</description><subject>4-Butyrolactone - analogs & derivatives</subject><subject>4-Butyrolactone - chemical synthesis</subject><subject>4-Butyrolactone - chemistry</subject><subject>4-Butyrolactone - pharmacology</subject><subject>aldehydes</subject><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antifungal</subject><subject>Antifungal agents</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>antifungal properties</subject><subject>Biological and medical sciences</subject><subject>Candida</subject><subject>Candida - drug effects</subject><subject>Candidiasis - drug therapy</subject><subject>Cell Line</subject><subject>Cell Line, Tumor</subject><subject>cell proliferation</subject><subject>condensation</subject><subject>Cyclopentanes - chemical synthesis</subject><subject>Cyclopentanes - chemistry</subject><subject>Cyclopentanes - pharmacology</subject><subject>Cyclopentenediones</subject><subject>Cytotoxicity</subject><subject>fluconazole</subject><subject>Humans</subject><subject>Knoevenagel</subject><subject>Lewis acid</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Microbial Sensitivity Tests</subject><subject>Pharmacology. Drug treatments</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqN0UFrFDEUB_AgFrtWv4AHnUvxNGOSl8lOwEspWi0FD7XgLWSSlzbLzKQms8X99s2wW71JLwmE33t5_B8h7xhtGGXy06bpRzs0nDLW0K6hrXpBVkxIUYOg7UuyokrSulPi1zF5nfOGUiaoEK_IMWeKAii2IpfXu2m-wxxyZSZX9SEO8TZYM1TGzuEhzLsq-sphHnG-i392RZkitpiXdxvTNlszxQmrszfkyJsh49vDfUJuvn75ef6tvvpx8f387Kq2QrC57iX03rVrdMp4KIdEzrnhHq1ae6nAoWsd9IYpBx6EaVurLK4lgw5lB3BCPu773qf4uwwy6zFki8NgJozbrDulChXd-hkSgHIFvEi-lzbFnBN6fZ_CaNJOM6qXsPVGL2HrJWxNO13CLkXvD-23_Yjub8lTugWcHoApKQ0-mcmG_M8JSRdY3Ie98yZqc5uKubkuP7VlY9AKWDp93gsswT4ETDrbgJNFFxLaWbsY_jfpIwWMpwM</recordid><startdate>20111015</startdate><enddate>20111015</enddate><creator>Tichotová, Lucie</creator><creator>Matoušová, Eliška</creator><creator>Špulák, Marcel</creator><creator>Kuneš, Jiří</creator><creator>Votruba, Ivan</creator><creator>Buchta, Vladimír</creator><creator>Pour, Milan</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><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>20111015</creationdate><title>Synthesis and biological activity of desmethoxy analogues of coruscanone A</title><author>Tichotová, Lucie ; Matoušová, Eliška ; Špulák, Marcel ; Kuneš, Jiří ; Votruba, Ivan ; Buchta, Vladimír ; Pour, Milan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c441t-b63bfd57ed9af3d9a6e222a2fec97f693ded5d3ba19d3f34a55c9ce76138e6833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>4-Butyrolactone - analogs & derivatives</topic><topic>4-Butyrolactone - chemical synthesis</topic><topic>4-Butyrolactone - chemistry</topic><topic>4-Butyrolactone - pharmacology</topic><topic>aldehydes</topic><topic>Animals</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antifungal</topic><topic>Antifungal agents</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>antifungal properties</topic><topic>Biological and medical sciences</topic><topic>Candida</topic><topic>Candida - drug effects</topic><topic>Candidiasis - drug therapy</topic><topic>Cell Line</topic><topic>Cell Line, Tumor</topic><topic>cell proliferation</topic><topic>condensation</topic><topic>Cyclopentanes - chemical synthesis</topic><topic>Cyclopentanes - chemistry</topic><topic>Cyclopentanes - pharmacology</topic><topic>Cyclopentenediones</topic><topic>Cytotoxicity</topic><topic>fluconazole</topic><topic>Humans</topic><topic>Knoevenagel</topic><topic>Lewis acid</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Microbial Sensitivity Tests</topic><topic>Pharmacology. Drug treatments</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tichotová, Lucie</creatorcontrib><creatorcontrib>Matoušová, Eliška</creatorcontrib><creatorcontrib>Špulák, Marcel</creatorcontrib><creatorcontrib>Kuneš, Jiří</creatorcontrib><creatorcontrib>Votruba, Ivan</creatorcontrib><creatorcontrib>Buchta, Vladimír</creatorcontrib><creatorcontrib>Pour, Milan</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</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>Tichotová, Lucie</au><au>Matoušová, Eliška</au><au>Špulák, Marcel</au><au>Kuneš, Jiří</au><au>Votruba, Ivan</au><au>Buchta, Vladimír</au><au>Pour, Milan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological activity of desmethoxy analogues of coruscanone A</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2011-10-15</date><risdate>2011</risdate><volume>21</volume><issue>20</issue><spage>6062</spage><epage>6066</epage><pages>6062-6066</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Desmethoxy analogues of coruscanone A were prepared via Ti(
iPrO)
4 mediated condensation of cyclopentenedione with aldehydes. Antifungal activity of 2-benzylidenecyclopent-4-ene-1,3-dione was comparable to those of coruscanone A and fluconazole, and was superior to the drug standard against several non-albicans
Candida species. Experiments on antiproliferative activity indicated lower cytotoxicity compared to the natural product.
A series of simple desmethoxy analogues of coruscanone A was prepared via a novel version of Ti(
iPrO)
4-mediated Knoevenagel condensation of cyclopentenedione with substituted benzaldehydes and cinnamic aldehydes, and the compounds were evaluated for antifungal activity and cytotoxicity. The most potent 2-benzylidenecyclopent-4-ene-1,3-dione possessed antifungal effect comparable to coruscanone A and a somewhat broader spectrum of activity against
Candida species. The compound was also superior to fluconazole against several non-albicans
Candida sp. Evaluation of the ability of the compound to influence cell proliferation using two different assays showed that 2-benzylidenecyclopent-4-ene-1,3-dione has lower cytotoxicity compared to the natural product.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>21903391</pmid><doi>10.1016/j.bmcl.2011.08.059</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2011-10, Vol.21 (20), p.6062-6066 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | 4-Butyrolactone - analogs & derivatives 4-Butyrolactone - chemical synthesis 4-Butyrolactone - chemistry 4-Butyrolactone - pharmacology aldehydes Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antifungal Antifungal agents Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology antifungal properties Biological and medical sciences Candida Candida - drug effects Candidiasis - drug therapy Cell Line Cell Line, Tumor cell proliferation condensation Cyclopentanes - chemical synthesis Cyclopentanes - chemistry Cyclopentanes - pharmacology Cyclopentenediones Cytotoxicity fluconazole Humans Knoevenagel Lewis acid Medical sciences Mice Microbial Sensitivity Tests Pharmacology. Drug treatments Structure-Activity Relationship |
| title | Synthesis and biological activity of desmethoxy analogues of coruscanone A |
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