Expedient on-resin synthesis of peptidic benzimidazoles
[Display omitted] The benzimidazole moiety is a ubiquitous pharmacophore present in numerous anthelmintic, antibacterial, antiviral, antineoplastic, and antifungal drugs. While the polypharmacology of this heterocycle has spurred the development of numerous solution-phase syntheses, only a handful o...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2018-09, Vol.28 (16), p.2679-2681 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Bird, Michael J. Silvestri, Anthony P. Dawson, Philip E. |
| description | [Display omitted]
The benzimidazole moiety is a ubiquitous pharmacophore present in numerous anthelmintic, antibacterial, antiviral, antineoplastic, and antifungal drugs. While the polypharmacology of this heterocycle has spurred the development of numerous solution-phase syntheses, only a handful of disparate and inefficient methods detailing its synthesis on-resin have been reported. Here we report the concise and expedient syntheses of internal and C-terminal peptidic benzimidazoles – an emerging class of peptide deformylase (PDF)-inhibiting antimicrobials. This method benefits from being performed wholly on solid-phase at room temperature resulting in minimal purification and tolerance of temperature-sensitive functionality. |
| doi_str_mv | 10.1016/j.bmcl.2018.04.062 |
| format | Article |
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The benzimidazole moiety is a ubiquitous pharmacophore present in numerous anthelmintic, antibacterial, antiviral, antineoplastic, and antifungal drugs. While the polypharmacology of this heterocycle has spurred the development of numerous solution-phase syntheses, only a handful of disparate and inefficient methods detailing its synthesis on-resin have been reported. Here we report the concise and expedient syntheses of internal and C-terminal peptidic benzimidazoles – an emerging class of peptide deformylase (PDF)-inhibiting antimicrobials. This method benefits from being performed wholly on solid-phase at room temperature resulting in minimal purification and tolerance of temperature-sensitive functionality.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2018.04.062</identifier><identifier>PMID: 29739642</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Anthelmintics ; Antifungals ; Antimicrobials ; Benzimidazoles ; Benzimidazoles - chemical synthesis ; Chemistry Techniques, Synthetic - methods ; Oligopeptides - chemical synthesis ; Peptide benzimidazoles ; Peptide therapeutics ; Resins, Synthetic - chemistry ; SPPS</subject><ispartof>Bioorganic & medicinal chemistry letters, 2018-09, Vol.28 (16), p.2679-2681</ispartof><rights>2018</rights><rights>Copyright © 2018. Published by Elsevier Ltd.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c455t-a67e94d8099cda3baf4ca616a295ff40d0ab97d1e26b0c40ae674cac2c15af3d3</citedby><cites>FETCH-LOGICAL-c455t-a67e94d8099cda3baf4ca616a295ff40d0ab97d1e26b0c40ae674cac2c15af3d3</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.2018.04.062$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3548,27922,27923,45993</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29739642$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bird, Michael J.</creatorcontrib><creatorcontrib>Silvestri, Anthony P.</creatorcontrib><creatorcontrib>Dawson, Philip E.</creatorcontrib><title>Expedient on-resin synthesis of peptidic benzimidazoles</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
The benzimidazole moiety is a ubiquitous pharmacophore present in numerous anthelmintic, antibacterial, antiviral, antineoplastic, and antifungal drugs. While the polypharmacology of this heterocycle has spurred the development of numerous solution-phase syntheses, only a handful of disparate and inefficient methods detailing its synthesis on-resin have been reported. Here we report the concise and expedient syntheses of internal and C-terminal peptidic benzimidazoles – an emerging class of peptide deformylase (PDF)-inhibiting antimicrobials. This method benefits from being performed wholly on solid-phase at room temperature resulting in minimal purification and tolerance of temperature-sensitive functionality.</description><subject>Anthelmintics</subject><subject>Antifungals</subject><subject>Antimicrobials</subject><subject>Benzimidazoles</subject><subject>Benzimidazoles - chemical synthesis</subject><subject>Chemistry Techniques, Synthetic - methods</subject><subject>Oligopeptides - chemical synthesis</subject><subject>Peptide benzimidazoles</subject><subject>Peptide therapeutics</subject><subject>Resins, Synthetic - chemistry</subject><subject>SPPS</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMFq3DAQhkVpabZpXyCH4mMvdkbyWLagBEJIm0CglxZ6E7I0brTYlit5Q5Onr5ZNQnPpaQbmm3-Gj7ETDhUHLk-3VT_ZsRLAuwqwAilesQ1HiWWN0LxmG1ASyk7hzyP2LqUtAEdAfMuOhGprJVFsWHv5ZyHnaV6LMJeRkp-LdD-vt7lLRRiKhZbVO2-LnuYHP3lnHsJI6T17M5gx0YfHesx-fLn8fnFV3nz7en1xflNabJq1NLIlha4DpawzdW8GtEZyaYRqhgHBgelV6zgJ2YNFMCTbTFhheWOG2tXH7OyQu-z6iZzNj0Yz6iX6ycR7HYzXLyezv9W_wp2W2HEuuxzw6TEght87SquefLI0jmamsEtaQC1bBVxgRsUBtTGkFGl4PsNB743rrd4b13vjGlBn43np478PPq88Kc7A5wNAWdOdp6iTzb5tth7JrtoF_7_8v57FlG4</recordid><startdate>20180901</startdate><enddate>20180901</enddate><creator>Bird, Michael J.</creator><creator>Silvestri, Anthony P.</creator><creator>Dawson, Philip E.</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><scope>5PM</scope></search><sort><creationdate>20180901</creationdate><title>Expedient on-resin synthesis of peptidic benzimidazoles</title><author>Bird, Michael J. ; Silvestri, Anthony P. ; Dawson, Philip E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c455t-a67e94d8099cda3baf4ca616a295ff40d0ab97d1e26b0c40ae674cac2c15af3d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Anthelmintics</topic><topic>Antifungals</topic><topic>Antimicrobials</topic><topic>Benzimidazoles</topic><topic>Benzimidazoles - chemical synthesis</topic><topic>Chemistry Techniques, Synthetic - methods</topic><topic>Oligopeptides - chemical synthesis</topic><topic>Peptide benzimidazoles</topic><topic>Peptide therapeutics</topic><topic>Resins, Synthetic - chemistry</topic><topic>SPPS</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bird, Michael J.</creatorcontrib><creatorcontrib>Silvestri, Anthony P.</creatorcontrib><creatorcontrib>Dawson, Philip E.</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><collection>PubMed Central (Full Participant titles)</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bird, Michael J.</au><au>Silvestri, Anthony P.</au><au>Dawson, Philip E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Expedient on-resin synthesis of peptidic benzimidazoles</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2018-09-01</date><risdate>2018</risdate><volume>28</volume><issue>16</issue><spage>2679</spage><epage>2681</epage><pages>2679-2681</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
The benzimidazole moiety is a ubiquitous pharmacophore present in numerous anthelmintic, antibacterial, antiviral, antineoplastic, and antifungal drugs. While the polypharmacology of this heterocycle has spurred the development of numerous solution-phase syntheses, only a handful of disparate and inefficient methods detailing its synthesis on-resin have been reported. Here we report the concise and expedient syntheses of internal and C-terminal peptidic benzimidazoles – an emerging class of peptide deformylase (PDF)-inhibiting antimicrobials. This method benefits from being performed wholly on solid-phase at room temperature resulting in minimal purification and tolerance of temperature-sensitive functionality.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>29739642</pmid><doi>10.1016/j.bmcl.2018.04.062</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2018-09, Vol.28 (16), p.2679-2681 |
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| source | Elsevier ScienceDirect Journals Complete - AutoHoldings; MEDLINE |
| subjects | Anthelmintics Antifungals Antimicrobials Benzimidazoles Benzimidazoles - chemical synthesis Chemistry Techniques, Synthetic - methods Oligopeptides - chemical synthesis Peptide benzimidazoles Peptide therapeutics Resins, Synthetic - chemistry SPPS |
| title | Expedient on-resin synthesis of peptidic benzimidazoles |
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