A facile synthesis of novel miconazole analogues and the evaluation of their antifungal activity
Four novel miconazole analogues (8–11) were synthetized and evaluated for activity against four filamentous fungi (Mucor hiemalis, Aspergillus fumigatus, Trichosporon cutaneum, and Rhizopus oryzae) and eight species of Candida as yeast specimens. Compounds 9 and 10 showed very good activity when eva...
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| Veröffentlicht in: | European journal of medicinal chemistry 2015-06, Vol.97, p.275-279 |
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| container_title | European journal of medicinal chemistry |
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| creator | Ramírez-Villalva, Alejandra González-Calderón, Davir González-Romero, Carlos Morales-Rodríguez, Macario Jauregui-Rodríguez, Bertha Cuevas-Yáñez, Erick Fuentes-Benítes, Aydeé |
| description | Four novel miconazole analogues (8–11) were synthetized and evaluated for activity against four filamentous fungi (Mucor hiemalis, Aspergillus fumigatus, Trichosporon cutaneum, and Rhizopus oryzae) and eight species of Candida as yeast specimens. Compounds 9 and 10 showed very good activity when evaluated in yeast (MIC 0.112 and 0.163 μg/mL) compared to the reference compound, itraconazole (MIC 0.067 μg/mL). The best antifungal activity in filamentous strains was shown by compound 9. Hence compounds 9 and 10 represent new leads for further pharmacomodulation in this series.
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•Miconazole analogues were synthetized through a facile synthetic strategy.•Evaluation against filamentous and yeast fungi.•Two of these compounds showed significant biological properties.•These results were consistent for both ATCC strains and clinical isolates. |
| doi_str_mv | 10.1016/j.ejmech.2015.04.047 |
| format | Article |
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•Miconazole analogues were synthetized through a facile synthetic strategy.•Evaluation against filamentous and yeast fungi.•Two of these compounds showed significant biological properties.•These results were consistent for both ATCC strains and clinical isolates.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2015.04.047</identifier><identifier>PMID: 25989345</identifier><language>eng</language><publisher>France: Elsevier Masson SAS</publisher><subject>Antifungal activity ; Antifungal Agents - chemical synthesis ; Antifungal Agents - pharmacology ; Benzoates - chemical synthesis ; Benzoates - pharmacology ; Dose-Response Relationship, Drug ; Fungi - drug effects ; Imidazoles - chemical synthesis ; Imidazoles - pharmacology ; Methanol - analogs & derivatives ; Methanol - chemical synthesis ; Methanol - pharmacology ; Miconazole - chemistry ; Miconazole derivatives ; Microbial Sensitivity Tests ; Minimum inhibitory concentration ; Mycoses - drug therapy ; Mycoses - microbiology</subject><ispartof>European journal of medicinal chemistry, 2015-06, Vol.97, p.275-279</ispartof><rights>2015 Elsevier Masson SAS</rights><rights>Copyright © 2015 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-863b588d0dcd4cdbdb23db6e97cf35bf97ab0a3acf264e7ab5f5260f838f9b523</citedby><cites>FETCH-LOGICAL-c362t-863b588d0dcd4cdbdb23db6e97cf35bf97ab0a3acf264e7ab5f5260f838f9b523</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0223523415300118$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25989345$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ramírez-Villalva, Alejandra</creatorcontrib><creatorcontrib>González-Calderón, Davir</creatorcontrib><creatorcontrib>González-Romero, Carlos</creatorcontrib><creatorcontrib>Morales-Rodríguez, Macario</creatorcontrib><creatorcontrib>Jauregui-Rodríguez, Bertha</creatorcontrib><creatorcontrib>Cuevas-Yáñez, Erick</creatorcontrib><creatorcontrib>Fuentes-Benítes, Aydeé</creatorcontrib><title>A facile synthesis of novel miconazole analogues and the evaluation of their antifungal activity</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Four novel miconazole analogues (8–11) were synthetized and evaluated for activity against four filamentous fungi (Mucor hiemalis, Aspergillus fumigatus, Trichosporon cutaneum, and Rhizopus oryzae) and eight species of Candida as yeast specimens. Compounds 9 and 10 showed very good activity when evaluated in yeast (MIC 0.112 and 0.163 μg/mL) compared to the reference compound, itraconazole (MIC 0.067 μg/mL). The best antifungal activity in filamentous strains was shown by compound 9. Hence compounds 9 and 10 represent new leads for further pharmacomodulation in this series.
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•Miconazole analogues were synthetized through a facile synthetic strategy.•Evaluation against filamentous and yeast fungi.•Two of these compounds showed significant biological properties.•These results were consistent for both ATCC strains and clinical isolates.</description><subject>Antifungal activity</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - pharmacology</subject><subject>Benzoates - chemical synthesis</subject><subject>Benzoates - pharmacology</subject><subject>Dose-Response Relationship, Drug</subject><subject>Fungi - drug effects</subject><subject>Imidazoles - chemical synthesis</subject><subject>Imidazoles - pharmacology</subject><subject>Methanol - analogs & derivatives</subject><subject>Methanol - chemical synthesis</subject><subject>Methanol - pharmacology</subject><subject>Miconazole - chemistry</subject><subject>Miconazole derivatives</subject><subject>Microbial Sensitivity Tests</subject><subject>Minimum inhibitory concentration</subject><subject>Mycoses - drug therapy</subject><subject>Mycoses - microbiology</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kF1LwzAUhoMobk7_gUgvvelM89X2RhjDLxh4o9cxTU62jLaZTVuYv96MqZfCgSTnPG_OOS9C1xmeZzgTd9s5bBvQmznBGZ9jFiM_QdMsF0VKCWenaIoJoSknlE3QRQhbjDEXGJ-jCeFlUVLGp-hjkVilXQ1J2Lf9BoILibdJ60eok8Zp36ovH6uqVbVfDxDizSQRTGBU9aB659uDIGZcF2u9s0O7VnWidO9G1-8v0ZlVdYCrn3OG3h8f3pbP6er16WW5WKWaCtKnhaAVLwqDjTZMm8pUhJpKQJlrS3lly1xVWFGlLREM4oNbTgS2BS1sWcUdZ-j2-O-u859xzl42Lmioa9WCH4LMRJFTJsoyiyg7orrzIXRg5a5zjer2MsPy4K3cyqO38uCtxCxGHmU3Px2GqgHzJ_o1MwL3RwDinqODTgbtoNVgXAe6l8a7_zt8A7JNjqE</recordid><startdate>20150605</startdate><enddate>20150605</enddate><creator>Ramírez-Villalva, Alejandra</creator><creator>González-Calderón, Davir</creator><creator>González-Romero, Carlos</creator><creator>Morales-Rodríguez, Macario</creator><creator>Jauregui-Rodríguez, Bertha</creator><creator>Cuevas-Yáñez, Erick</creator><creator>Fuentes-Benítes, Aydeé</creator><general>Elsevier Masson SAS</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>20150605</creationdate><title>A facile synthesis of novel miconazole analogues and the evaluation of their antifungal activity</title><author>Ramírez-Villalva, Alejandra ; González-Calderón, Davir ; González-Romero, Carlos ; Morales-Rodríguez, Macario ; Jauregui-Rodríguez, Bertha ; Cuevas-Yáñez, Erick ; Fuentes-Benítes, Aydeé</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-863b588d0dcd4cdbdb23db6e97cf35bf97ab0a3acf264e7ab5f5260f838f9b523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Antifungal activity</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - pharmacology</topic><topic>Benzoates - chemical synthesis</topic><topic>Benzoates - pharmacology</topic><topic>Dose-Response Relationship, Drug</topic><topic>Fungi - drug effects</topic><topic>Imidazoles - chemical synthesis</topic><topic>Imidazoles - pharmacology</topic><topic>Methanol - analogs & derivatives</topic><topic>Methanol - chemical synthesis</topic><topic>Methanol - pharmacology</topic><topic>Miconazole - chemistry</topic><topic>Miconazole derivatives</topic><topic>Microbial Sensitivity Tests</topic><topic>Minimum inhibitory concentration</topic><topic>Mycoses - drug therapy</topic><topic>Mycoses - microbiology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ramírez-Villalva, Alejandra</creatorcontrib><creatorcontrib>González-Calderón, Davir</creatorcontrib><creatorcontrib>González-Romero, Carlos</creatorcontrib><creatorcontrib>Morales-Rodríguez, Macario</creatorcontrib><creatorcontrib>Jauregui-Rodríguez, Bertha</creatorcontrib><creatorcontrib>Cuevas-Yáñez, Erick</creatorcontrib><creatorcontrib>Fuentes-Benítes, Aydeé</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>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ramírez-Villalva, Alejandra</au><au>González-Calderón, Davir</au><au>González-Romero, Carlos</au><au>Morales-Rodríguez, Macario</au><au>Jauregui-Rodríguez, Bertha</au><au>Cuevas-Yáñez, Erick</au><au>Fuentes-Benítes, Aydeé</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A facile synthesis of novel miconazole analogues and the evaluation of their antifungal activity</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2015-06-05</date><risdate>2015</risdate><volume>97</volume><spage>275</spage><epage>279</epage><pages>275-279</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><abstract>Four novel miconazole analogues (8–11) were synthetized and evaluated for activity against four filamentous fungi (Mucor hiemalis, Aspergillus fumigatus, Trichosporon cutaneum, and Rhizopus oryzae) and eight species of Candida as yeast specimens. Compounds 9 and 10 showed very good activity when evaluated in yeast (MIC 0.112 and 0.163 μg/mL) compared to the reference compound, itraconazole (MIC 0.067 μg/mL). The best antifungal activity in filamentous strains was shown by compound 9. Hence compounds 9 and 10 represent new leads for further pharmacomodulation in this series.
[Display omitted]
•Miconazole analogues were synthetized through a facile synthetic strategy.•Evaluation against filamentous and yeast fungi.•Two of these compounds showed significant biological properties.•These results were consistent for both ATCC strains and clinical isolates.</abstract><cop>France</cop><pub>Elsevier Masson SAS</pub><pmid>25989345</pmid><doi>10.1016/j.ejmech.2015.04.047</doi><tpages>5</tpages></addata></record> |
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| subjects | Antifungal activity Antifungal Agents - chemical synthesis Antifungal Agents - pharmacology Benzoates - chemical synthesis Benzoates - pharmacology Dose-Response Relationship, Drug Fungi - drug effects Imidazoles - chemical synthesis Imidazoles - pharmacology Methanol - analogs & derivatives Methanol - chemical synthesis Methanol - pharmacology Miconazole - chemistry Miconazole derivatives Microbial Sensitivity Tests Minimum inhibitory concentration Mycoses - drug therapy Mycoses - microbiology |
| title | A facile synthesis of novel miconazole analogues and the evaluation of their antifungal activity |
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