Benzofuro[3,2-d]pyrimidines inspired from cercosporamide CaPkc1 inhibitor: Synthesis and evaluation of fluconazole susceptibility restoration
[Display omitted] •Heterocyclic compounds inspired from cercosporamide were synthesized.•Synergistic effect with fluconazole on inhibition of cell growth of a Candida albicans resistant strain is reported.•Kinase inhibitory activity was detected. In a context of growing resistance to classical antif...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2018-07, Vol.28 (13), p.2250-2255 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Dao, Viet Hung Ourliac-Garnier, Isabelle Bazin, Marc-Antoine Jacquot, Catherine Baratte, Blandine Ruchaud, Sandrine Bach, Stéphane Grovel, Olivier Le Pape, Patrice Marchand, Pascal |
| description | [Display omitted]
•Heterocyclic compounds inspired from cercosporamide were synthesized.•Synergistic effect with fluconazole on inhibition of cell growth of a Candida albicans resistant strain is reported.•Kinase inhibitory activity was detected.
In a context of growing resistance to classical antifungal therapy, the design of new drugs targeting alternative pathways is highly expected. Benzofuro[3,2-d]pyrimidine derivatives, derived from (−)-cercosporamide, were synthesized and evaluated as potential Candida albicans PKC inhibitors in the aim of restoring susceptibility to azole treatment. Co-administration assay of benzofuropyrimidinedione 23 and fluconazole highlighted a synergistic effect on inhibition of cell growth of a Candida albicans resistant strain. |
| doi_str_mv | 10.1016/j.bmcl.2018.05.044 |
| format | Article |
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•Heterocyclic compounds inspired from cercosporamide were synthesized.•Synergistic effect with fluconazole on inhibition of cell growth of a Candida albicans resistant strain is reported.•Kinase inhibitory activity was detected.
In a context of growing resistance to classical antifungal therapy, the design of new drugs targeting alternative pathways is highly expected. Benzofuro[3,2-d]pyrimidine derivatives, derived from (−)-cercosporamide, were synthesized and evaluated as potential Candida albicans PKC inhibitors in the aim of restoring susceptibility to azole treatment. Co-administration assay of benzofuropyrimidinedione 23 and fluconazole highlighted a synergistic effect on inhibition of cell growth of a Candida albicans resistant strain.</description><identifier>ISSN: 0960-894X</identifier><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3405</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmcl.2018.05.044</identifier><identifier>PMID: 29853332</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Antifungal activity ; Benzofuro[3,2-d]pyrimidine ; Candida albicans Pkc1 ; Cercosporamide ; Chemical Sciences ; Fluconazole susceptibility restoration ; Life Sciences</subject><ispartof>Bioorganic & medicinal chemistry, 2018-07, Vol.28 (13), p.2250-2255</ispartof><rights>2018 Elsevier Ltd</rights><rights>Copyright © 2018 Elsevier Ltd. All rights reserved.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-9b2725e3fe34fccbea604ac4be8171f0f5f597375f6a41a062e7b3ae81e4f9c63</citedby><cites>FETCH-LOGICAL-c390t-9b2725e3fe34fccbea604ac4be8171f0f5f597375f6a41a062e7b3ae81e4f9c63</cites><orcidid>0000-0001-7773-8642 ; 0000-0002-2064-9558 ; 0000-0002-7186-7483 ; 0000-0002-8159-0959 ; 0000-0001-5059-6402 ; 0000-0003-0987-5404 ; 0000-0002-5077-5192 ; 0000-0002-4606-6625 ; 0000-0003-3165-4771</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2018.05.044$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,776,780,881,3536,27903,27904,45974</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29853332$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-03011408$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Dao, Viet Hung</creatorcontrib><creatorcontrib>Ourliac-Garnier, Isabelle</creatorcontrib><creatorcontrib>Bazin, Marc-Antoine</creatorcontrib><creatorcontrib>Jacquot, Catherine</creatorcontrib><creatorcontrib>Baratte, Blandine</creatorcontrib><creatorcontrib>Ruchaud, Sandrine</creatorcontrib><creatorcontrib>Bach, Stéphane</creatorcontrib><creatorcontrib>Grovel, Olivier</creatorcontrib><creatorcontrib>Le Pape, Patrice</creatorcontrib><creatorcontrib>Marchand, Pascal</creatorcontrib><title>Benzofuro[3,2-d]pyrimidines inspired from cercosporamide CaPkc1 inhibitor: Synthesis and evaluation of fluconazole susceptibility restoration</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
•Heterocyclic compounds inspired from cercosporamide were synthesized.•Synergistic effect with fluconazole on inhibition of cell growth of a Candida albicans resistant strain is reported.•Kinase inhibitory activity was detected.
In a context of growing resistance to classical antifungal therapy, the design of new drugs targeting alternative pathways is highly expected. Benzofuro[3,2-d]pyrimidine derivatives, derived from (−)-cercosporamide, were synthesized and evaluated as potential Candida albicans PKC inhibitors in the aim of restoring susceptibility to azole treatment. Co-administration assay of benzofuropyrimidinedione 23 and fluconazole highlighted a synergistic effect on inhibition of cell growth of a Candida albicans resistant strain.</description><subject>Antifungal activity</subject><subject>Benzofuro[3,2-d]pyrimidine</subject><subject>Candida albicans Pkc1</subject><subject>Cercosporamide</subject><subject>Chemical Sciences</subject><subject>Fluconazole susceptibility restoration</subject><subject>Life Sciences</subject><issn>0960-894X</issn><issn>0968-0896</issn><issn>1464-3405</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp9kV2L1DAUhoMo7uzqH_BCcqlg60mT9EP2Zh1WVxhQUEEQCWl6wmRsm5q0A7P_wf9sxln30qtA8rwvJ-ch5BmDnAErX-_ydjB9XgCrc5A5CPGArJgoRcYFyIdkBU0JWd2Ib2fkPMYdABMJekzOiqaWnPNiRX6_xfHW2yX47_xVkXU_pkNwg-vciJG6MU4uYEdt8AM1GIyPkw86vSNd608_DUvM1rVu9uEN_XwY5y1GF6keO4p73S96dn6k3lLbL8aP-tb3SOMSDU5zivVuPtCAMcX_kk_II6v7iE_vzgvy9d31l_VNtvn4_sP6apMZ3sCcNW1RFRK5RS6sMS3qEoQ2osWaVcyClVY2Fa-kLbVgGsoCq5br9IrCNqbkF-TlqXerezWlD-twUF47dXO1Ucc74MDSsuo9S-yLEzsF_2tJs6rBpfn7Xo_ol6gKEI2UNa8hocUJNcHHGNDedzNQR2Vqp47K1FGZAqmSjRR6fte_tAN295F_jhJweQIwbWTvMKhoHI4Gu-TGzKrz7n_9fwD-Rasd</recordid><startdate>20180715</startdate><enddate>20180715</enddate><creator>Dao, Viet Hung</creator><creator>Ourliac-Garnier, Isabelle</creator><creator>Bazin, Marc-Antoine</creator><creator>Jacquot, Catherine</creator><creator>Baratte, Blandine</creator><creator>Ruchaud, Sandrine</creator><creator>Bach, Stéphane</creator><creator>Grovel, Olivier</creator><creator>Le Pape, Patrice</creator><creator>Marchand, Pascal</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0001-7773-8642</orcidid><orcidid>https://orcid.org/0000-0002-2064-9558</orcidid><orcidid>https://orcid.org/0000-0002-7186-7483</orcidid><orcidid>https://orcid.org/0000-0002-8159-0959</orcidid><orcidid>https://orcid.org/0000-0001-5059-6402</orcidid><orcidid>https://orcid.org/0000-0003-0987-5404</orcidid><orcidid>https://orcid.org/0000-0002-5077-5192</orcidid><orcidid>https://orcid.org/0000-0002-4606-6625</orcidid><orcidid>https://orcid.org/0000-0003-3165-4771</orcidid></search><sort><creationdate>20180715</creationdate><title>Benzofuro[3,2-d]pyrimidines inspired from cercosporamide CaPkc1 inhibitor: Synthesis and evaluation of fluconazole susceptibility restoration</title><author>Dao, Viet Hung ; Ourliac-Garnier, Isabelle ; Bazin, Marc-Antoine ; Jacquot, Catherine ; Baratte, Blandine ; Ruchaud, Sandrine ; Bach, Stéphane ; Grovel, Olivier ; Le Pape, Patrice ; Marchand, Pascal</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-9b2725e3fe34fccbea604ac4be8171f0f5f597375f6a41a062e7b3ae81e4f9c63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Antifungal activity</topic><topic>Benzofuro[3,2-d]pyrimidine</topic><topic>Candida albicans Pkc1</topic><topic>Cercosporamide</topic><topic>Chemical Sciences</topic><topic>Fluconazole susceptibility restoration</topic><topic>Life Sciences</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dao, Viet Hung</creatorcontrib><creatorcontrib>Ourliac-Garnier, Isabelle</creatorcontrib><creatorcontrib>Bazin, Marc-Antoine</creatorcontrib><creatorcontrib>Jacquot, Catherine</creatorcontrib><creatorcontrib>Baratte, Blandine</creatorcontrib><creatorcontrib>Ruchaud, Sandrine</creatorcontrib><creatorcontrib>Bach, Stéphane</creatorcontrib><creatorcontrib>Grovel, Olivier</creatorcontrib><creatorcontrib>Le Pape, Patrice</creatorcontrib><creatorcontrib>Marchand, Pascal</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dao, Viet Hung</au><au>Ourliac-Garnier, Isabelle</au><au>Bazin, Marc-Antoine</au><au>Jacquot, Catherine</au><au>Baratte, Blandine</au><au>Ruchaud, Sandrine</au><au>Bach, Stéphane</au><au>Grovel, Olivier</au><au>Le Pape, Patrice</au><au>Marchand, Pascal</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Benzofuro[3,2-d]pyrimidines inspired from cercosporamide CaPkc1 inhibitor: Synthesis and evaluation of fluconazole susceptibility restoration</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2018-07-15</date><risdate>2018</risdate><volume>28</volume><issue>13</issue><spage>2250</spage><epage>2255</epage><pages>2250-2255</pages><issn>0960-894X</issn><issn>0968-0896</issn><eissn>1464-3405</eissn><eissn>1464-3391</eissn><abstract>[Display omitted]
•Heterocyclic compounds inspired from cercosporamide were synthesized.•Synergistic effect with fluconazole on inhibition of cell growth of a Candida albicans resistant strain is reported.•Kinase inhibitory activity was detected.
In a context of growing resistance to classical antifungal therapy, the design of new drugs targeting alternative pathways is highly expected. Benzofuro[3,2-d]pyrimidine derivatives, derived from (−)-cercosporamide, were synthesized and evaluated as potential Candida albicans PKC inhibitors in the aim of restoring susceptibility to azole treatment. Co-administration assay of benzofuropyrimidinedione 23 and fluconazole highlighted a synergistic effect on inhibition of cell growth of a Candida albicans resistant strain.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>29853332</pmid><doi>10.1016/j.bmcl.2018.05.044</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-7773-8642</orcidid><orcidid>https://orcid.org/0000-0002-2064-9558</orcidid><orcidid>https://orcid.org/0000-0002-7186-7483</orcidid><orcidid>https://orcid.org/0000-0002-8159-0959</orcidid><orcidid>https://orcid.org/0000-0001-5059-6402</orcidid><orcidid>https://orcid.org/0000-0003-0987-5404</orcidid><orcidid>https://orcid.org/0000-0002-5077-5192</orcidid><orcidid>https://orcid.org/0000-0002-4606-6625</orcidid><orcidid>https://orcid.org/0000-0003-3165-4771</orcidid></addata></record> |
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| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | Antifungal activity Benzofuro[3,2-d]pyrimidine Candida albicans Pkc1 Cercosporamide Chemical Sciences Fluconazole susceptibility restoration Life Sciences |
| title | Benzofuro[3,2-d]pyrimidines inspired from cercosporamide CaPkc1 inhibitor: Synthesis and evaluation of fluconazole susceptibility restoration |
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