An amidation/cyclization approach to the synthesis of N-hydroxyquinolinones and their biological evaluation as potential anti-plasmodial, anti-bacterial, and iron(II)-chelating agents
[Display omitted] A 26-member library of novel N-hydroxyquinolinone derivatives was synthesized by a one-pot Buchwald-type palladium catalyzed amidation and condensation sequence. The design of these rare scaffolds was inspired from N-hydroxypyridones and 2-quinolinones classes of compounds which ha...
Gespeichert in:
| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2015-02, Vol.25 (3), p.607-610 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 610 |
|---|---|
| container_issue | 3 |
| container_start_page | 607 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 25 |
| creator | Teng, Yanbo Suwanarusk, Rossarin Ngai, Mun Hong Srinivasan, Rajavel Ong, Alice Soh Meoy Ho, Bow Rénia, Laurent Chai, Christina L.L. |
| description | [Display omitted]
A 26-member library of novel N-hydroxyquinolinone derivatives was synthesized by a one-pot Buchwald-type palladium catalyzed amidation and condensation sequence. The design of these rare scaffolds was inspired from N-hydroxypyridones and 2-quinolinones classes of compounds which have been shown to have rich biological activities. The synthesized compounds were evaluated for their anti-plasmodial and anti-bacterial properties. In addition, these compounds were screened for their iron(II)-chelation properties. Notably, four of these compounds exhibited anti-plasmodial activities comparable to that of the natural product cordypyridone B. |
| doi_str_mv | 10.1016/j.bmcl.2014.12.014 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1660390464</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0960894X14013110</els_id><sourcerecordid>1660390464</sourcerecordid><originalsourceid>FETCH-LOGICAL-c389t-35fa7c7eaf9bf7c5ebc80231d8cb901b04811d5b93cea6a3ba6d89f859bf95673</originalsourceid><addsrcrecordid>eNqNkUuLFDEUhYMoTjv6B1xIliNYNUlV6hFwMww-GgbdKLgLedzqTpNKapKqwfKP-fdM261LcRFO7uW7Z3EOQi8pKSmh7fWhVKN2ZUUoK2lVZnmENpS1rKgZaR6jDeEtKXrOvl2gZykdSCYIY0_RRdU0jNUd2aCfNx7L0Ro52-Cv9aqd_fH7j-U0xSD1Hs8Bz3vAafVZkk04DPhTsV9NDN_X-8X64PLzkLD05ojaiJUNLuyslg7Dg3TL2TLhKczgZ5v3MksxOZnGYPL85rRQUs8Qz7PBNgZ_td2-LvQeXDbxOyx32SA9R08G6RK8OOsl-vr-3Zfbj8Xd5w_b25u7Qtc9n4u6GWSnO5ADV0OnG1C6J1VNTa8VJ1QR1lNqGsVrDbKVtZKt6fnQNxnnTdvVl-jq5JvDuF8gzWK0SYNz0kNYkqBtS2pOcuj_gTYVo5xXJKPVCdUxpBRhEFO0o4yroEQcuxUHcexWHLsVtBJZ8tGrs_-iRjB_T_6UmYG3JwByIA8WokjagtdgbAQ9CxPsv_x_AV3gujk</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1652419920</pqid></control><display><type>article</type><title>An amidation/cyclization approach to the synthesis of N-hydroxyquinolinones and their biological evaluation as potential anti-plasmodial, anti-bacterial, and iron(II)-chelating agents</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals</source><creator>Teng, Yanbo ; Suwanarusk, Rossarin ; Ngai, Mun Hong ; Srinivasan, Rajavel ; Ong, Alice Soh Meoy ; Ho, Bow ; Rénia, Laurent ; Chai, Christina L.L.</creator><creatorcontrib>Teng, Yanbo ; Suwanarusk, Rossarin ; Ngai, Mun Hong ; Srinivasan, Rajavel ; Ong, Alice Soh Meoy ; Ho, Bow ; Rénia, Laurent ; Chai, Christina L.L.</creatorcontrib><description>[Display omitted]
A 26-member library of novel N-hydroxyquinolinone derivatives was synthesized by a one-pot Buchwald-type palladium catalyzed amidation and condensation sequence. The design of these rare scaffolds was inspired from N-hydroxypyridones and 2-quinolinones classes of compounds which have been shown to have rich biological activities. The synthesized compounds were evaluated for their anti-plasmodial and anti-bacterial properties. In addition, these compounds were screened for their iron(II)-chelation properties. Notably, four of these compounds exhibited anti-plasmodial activities comparable to that of the natural product cordypyridone B.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2014.12.014</identifier><identifier>PMID: 25544370</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Amides - chemistry ; Anti-bacterial activity ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Anti-plasmodial activity ; Antimalarials - chemical synthesis ; Antimalarials - chemistry ; Antimalarials - pharmacology ; Catalysis ; Chelating Agents - chemical synthesis ; Chelating Agents - chemistry ; Chelating Agents - pharmacology ; Cyclization ; Escherichia coli - drug effects ; Ferrous Compounds - chemistry ; Iron chelation ; N-Hydroxyquinolinone ; Palladium - chemistry ; Plasmodium - drug effects ; Quinolones - chemical synthesis ; Quinolones - chemistry ; Quinolones - pharmacology ; Staphylococcus aureus - drug effects ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2015-02, Vol.25 (3), p.607-610</ispartof><rights>2014 Elsevier Ltd</rights><rights>Copyright © 2014 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-35fa7c7eaf9bf7c5ebc80231d8cb901b04811d5b93cea6a3ba6d89f859bf95673</citedby><cites>FETCH-LOGICAL-c389t-35fa7c7eaf9bf7c5ebc80231d8cb901b04811d5b93cea6a3ba6d89f859bf95673</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X14013110$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25544370$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Teng, Yanbo</creatorcontrib><creatorcontrib>Suwanarusk, Rossarin</creatorcontrib><creatorcontrib>Ngai, Mun Hong</creatorcontrib><creatorcontrib>Srinivasan, Rajavel</creatorcontrib><creatorcontrib>Ong, Alice Soh Meoy</creatorcontrib><creatorcontrib>Ho, Bow</creatorcontrib><creatorcontrib>Rénia, Laurent</creatorcontrib><creatorcontrib>Chai, Christina L.L.</creatorcontrib><title>An amidation/cyclization approach to the synthesis of N-hydroxyquinolinones and their biological evaluation as potential anti-plasmodial, anti-bacterial, and iron(II)-chelating agents</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
A 26-member library of novel N-hydroxyquinolinone derivatives was synthesized by a one-pot Buchwald-type palladium catalyzed amidation and condensation sequence. The design of these rare scaffolds was inspired from N-hydroxypyridones and 2-quinolinones classes of compounds which have been shown to have rich biological activities. The synthesized compounds were evaluated for their anti-plasmodial and anti-bacterial properties. In addition, these compounds were screened for their iron(II)-chelation properties. Notably, four of these compounds exhibited anti-plasmodial activities comparable to that of the natural product cordypyridone B.</description><subject>Amides - chemistry</subject><subject>Anti-bacterial activity</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Anti-plasmodial activity</subject><subject>Antimalarials - chemical synthesis</subject><subject>Antimalarials - chemistry</subject><subject>Antimalarials - pharmacology</subject><subject>Catalysis</subject><subject>Chelating Agents - chemical synthesis</subject><subject>Chelating Agents - chemistry</subject><subject>Chelating Agents - pharmacology</subject><subject>Cyclization</subject><subject>Escherichia coli - drug effects</subject><subject>Ferrous Compounds - chemistry</subject><subject>Iron chelation</subject><subject>N-Hydroxyquinolinone</subject><subject>Palladium - chemistry</subject><subject>Plasmodium - drug effects</subject><subject>Quinolones - chemical synthesis</subject><subject>Quinolones - chemistry</subject><subject>Quinolones - pharmacology</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkUuLFDEUhYMoTjv6B1xIliNYNUlV6hFwMww-GgbdKLgLedzqTpNKapKqwfKP-fdM261LcRFO7uW7Z3EOQi8pKSmh7fWhVKN2ZUUoK2lVZnmENpS1rKgZaR6jDeEtKXrOvl2gZykdSCYIY0_RRdU0jNUd2aCfNx7L0Ro52-Cv9aqd_fH7j-U0xSD1Hs8Bz3vAafVZkk04DPhTsV9NDN_X-8X64PLzkLD05ojaiJUNLuyslg7Dg3TL2TLhKczgZ5v3MksxOZnGYPL85rRQUs8Qz7PBNgZ_td2-LvQeXDbxOyx32SA9R08G6RK8OOsl-vr-3Zfbj8Xd5w_b25u7Qtc9n4u6GWSnO5ADV0OnG1C6J1VNTa8VJ1QR1lNqGsVrDbKVtZKt6fnQNxnnTdvVl-jq5JvDuF8gzWK0SYNz0kNYkqBtS2pOcuj_gTYVo5xXJKPVCdUxpBRhEFO0o4yroEQcuxUHcexWHLsVtBJZ8tGrs_-iRjB_T_6UmYG3JwByIA8WokjagtdgbAQ9CxPsv_x_AV3gujk</recordid><startdate>20150201</startdate><enddate>20150201</enddate><creator>Teng, Yanbo</creator><creator>Suwanarusk, Rossarin</creator><creator>Ngai, Mun Hong</creator><creator>Srinivasan, Rajavel</creator><creator>Ong, Alice Soh Meoy</creator><creator>Ho, Bow</creator><creator>Rénia, Laurent</creator><creator>Chai, Christina L.L.</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>7QL</scope><scope>7QO</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20150201</creationdate><title>An amidation/cyclization approach to the synthesis of N-hydroxyquinolinones and their biological evaluation as potential anti-plasmodial, anti-bacterial, and iron(II)-chelating agents</title><author>Teng, Yanbo ; Suwanarusk, Rossarin ; Ngai, Mun Hong ; Srinivasan, Rajavel ; Ong, Alice Soh Meoy ; Ho, Bow ; Rénia, Laurent ; Chai, Christina L.L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-35fa7c7eaf9bf7c5ebc80231d8cb901b04811d5b93cea6a3ba6d89f859bf95673</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Amides - chemistry</topic><topic>Anti-bacterial activity</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Anti-plasmodial activity</topic><topic>Antimalarials - chemical synthesis</topic><topic>Antimalarials - chemistry</topic><topic>Antimalarials - pharmacology</topic><topic>Catalysis</topic><topic>Chelating Agents - chemical synthesis</topic><topic>Chelating Agents - chemistry</topic><topic>Chelating Agents - pharmacology</topic><topic>Cyclization</topic><topic>Escherichia coli - drug effects</topic><topic>Ferrous Compounds - chemistry</topic><topic>Iron chelation</topic><topic>N-Hydroxyquinolinone</topic><topic>Palladium - chemistry</topic><topic>Plasmodium - drug effects</topic><topic>Quinolones - chemical synthesis</topic><topic>Quinolones - chemistry</topic><topic>Quinolones - pharmacology</topic><topic>Staphylococcus aureus - drug effects</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Teng, Yanbo</creatorcontrib><creatorcontrib>Suwanarusk, Rossarin</creatorcontrib><creatorcontrib>Ngai, Mun Hong</creatorcontrib><creatorcontrib>Srinivasan, Rajavel</creatorcontrib><creatorcontrib>Ong, Alice Soh Meoy</creatorcontrib><creatorcontrib>Ho, Bow</creatorcontrib><creatorcontrib>Rénia, Laurent</creatorcontrib><creatorcontrib>Chai, Christina L.L.</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>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</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>Teng, Yanbo</au><au>Suwanarusk, Rossarin</au><au>Ngai, Mun Hong</au><au>Srinivasan, Rajavel</au><au>Ong, Alice Soh Meoy</au><au>Ho, Bow</au><au>Rénia, Laurent</au><au>Chai, Christina L.L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An amidation/cyclization approach to the synthesis of N-hydroxyquinolinones and their biological evaluation as potential anti-plasmodial, anti-bacterial, and iron(II)-chelating agents</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2015-02-01</date><risdate>2015</risdate><volume>25</volume><issue>3</issue><spage>607</spage><epage>610</epage><pages>607-610</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
A 26-member library of novel N-hydroxyquinolinone derivatives was synthesized by a one-pot Buchwald-type palladium catalyzed amidation and condensation sequence. The design of these rare scaffolds was inspired from N-hydroxypyridones and 2-quinolinones classes of compounds which have been shown to have rich biological activities. The synthesized compounds were evaluated for their anti-plasmodial and anti-bacterial properties. In addition, these compounds were screened for their iron(II)-chelation properties. Notably, four of these compounds exhibited anti-plasmodial activities comparable to that of the natural product cordypyridone B.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>25544370</pmid><doi>10.1016/j.bmcl.2014.12.014</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2015-02, Vol.25 (3), p.607-610 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1660390464 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Amides - chemistry Anti-bacterial activity Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Anti-plasmodial activity Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Catalysis Chelating Agents - chemical synthesis Chelating Agents - chemistry Chelating Agents - pharmacology Cyclization Escherichia coli - drug effects Ferrous Compounds - chemistry Iron chelation N-Hydroxyquinolinone Palladium - chemistry Plasmodium - drug effects Quinolones - chemical synthesis Quinolones - chemistry Quinolones - pharmacology Staphylococcus aureus - drug effects Structure-Activity Relationship |
| title | An amidation/cyclization approach to the synthesis of N-hydroxyquinolinones and their biological evaluation as potential anti-plasmodial, anti-bacterial, and iron(II)-chelating agents |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-31T16%3A50%3A30IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=An%20amidation/cyclization%20approach%20to%20the%20synthesis%20of%20N-hydroxyquinolinones%20and%20their%20biological%20evaluation%20as%20potential%20anti-plasmodial,%20anti-bacterial,%20and%20iron(II)-chelating%20agents&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry%20letters&rft.au=Teng,%20Yanbo&rft.date=2015-02-01&rft.volume=25&rft.issue=3&rft.spage=607&rft.epage=610&rft.pages=607-610&rft.issn=0960-894X&rft.eissn=1464-3405&rft_id=info:doi/10.1016/j.bmcl.2014.12.014&rft_dat=%3Cproquest_cross%3E1660390464%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1652419920&rft_id=info:pmid/25544370&rft_els_id=S0960894X14013110&rfr_iscdi=true |