Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group
The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B =...
Gespeichert in:
| Veröffentlicht in: | Journal of medicinal chemistry 1989-08, Vol.32 (8), p.1673-1681 |
|---|---|
| Hauptverfasser: | , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1681 |
|---|---|
| container_issue | 8 |
| container_start_page | 1673 |
| container_title | Journal of medicinal chemistry |
| container_volume | 32 |
| creator | Gregory, Walter A Brittelli, David R Wang, C. L. J Wuonola, Mark A McRipley, Ronald J Eustice, David C Eberly, Virginia S Slee, Andrew M Forbes, Martin Bartholomew, P. T |
| description | The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described. |
| doi_str_mv | 10.1021/jm00128a003 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_79115314</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>15357329</sourcerecordid><originalsourceid>FETCH-LOGICAL-a451t-924e1f13080dfa6664b0fd65c7793defb35384f66f1ef17e894b3b4c14d9ffc83</originalsourceid><addsrcrecordid>eNqFkM1vEzEUxC0EakPhxLnSnugBOfj5Y717bCMoSBEgNZwt79punW7WwfZWCX89jhJVHJA4PWnmp3maQegdkDkQCh_XG0KANpoQ9gLNQFCCeUP4SzQjhFJMa8rO0euU1qQQQNkZOqOCFFnOkLkes-90n230ekjz6m4_5gebfKr0aKqU49TnKVpcEP_k875Ik_E2VcFVDOu4HzDFYRfCTv8Ogzd-tCUF5tXqwVY31X0M0_YNeuVKuH17uhfo5-dPq8UXvPx--3VxvcSaC8i4pdyCA0YaYpyu65p3xJla9FK2zFjXMcEa7uragXUgbdPyjnW8B25a5_qGXaD3x9xtDL8mm7La-NTbYdCjDVNSsgUQDPh_wUIJyWhbwA9HsI8hpWid2ka_Ka0VEHUYX_01fqEvT7FTt7HmmT2tXXx89H3Kdvds6_ioasmkUKsfd2p5u_gmiWDq0OfqyOs-qXWY4ljW--fnP6spmh0</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>15357329</pqid></control><display><type>article</type><title>Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Gregory, Walter A ; Brittelli, David R ; Wang, C. L. J ; Wuonola, Mark A ; McRipley, Ronald J ; Eustice, David C ; Eberly, Virginia S ; Slee, Andrew M ; Forbes, Martin ; Bartholomew, P. T</creator><creatorcontrib>Gregory, Walter A ; Brittelli, David R ; Wang, C. L. J ; Wuonola, Mark A ; McRipley, Ronald J ; Eustice, David C ; Eberly, Virginia S ; Slee, Andrew M ; Forbes, Martin ; Bartholomew, P. T</creatorcontrib><description>The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00128a003</identifier><identifier>PMID: 2502627</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - pharmacology ; Chemical Phenomena ; Chemistry ; Enterococcus faecalis - drug effects ; Escherichia coli - drug effects ; Microbial Sensitivity Tests ; Oxazoles - chemical synthesis ; Oxazoles - pharmacology ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 1989-08, Vol.32 (8), p.1673-1681</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a451t-924e1f13080dfa6664b0fd65c7793defb35384f66f1ef17e894b3b4c14d9ffc83</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00128a003$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00128a003$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2502627$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gregory, Walter A</creatorcontrib><creatorcontrib>Brittelli, David R</creatorcontrib><creatorcontrib>Wang, C. L. J</creatorcontrib><creatorcontrib>Wuonola, Mark A</creatorcontrib><creatorcontrib>McRipley, Ronald J</creatorcontrib><creatorcontrib>Eustice, David C</creatorcontrib><creatorcontrib>Eberly, Virginia S</creatorcontrib><creatorcontrib>Slee, Andrew M</creatorcontrib><creatorcontrib>Forbes, Martin</creatorcontrib><creatorcontrib>Bartholomew, P. T</creatorcontrib><title>Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described.</description><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Enterococcus faecalis - drug effects</subject><subject>Escherichia coli - drug effects</subject><subject>Microbial Sensitivity Tests</subject><subject>Oxazoles - chemical synthesis</subject><subject>Oxazoles - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1989</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM1vEzEUxC0EakPhxLnSnugBOfj5Y717bCMoSBEgNZwt79punW7WwfZWCX89jhJVHJA4PWnmp3maQegdkDkQCh_XG0KANpoQ9gLNQFCCeUP4SzQjhFJMa8rO0euU1qQQQNkZOqOCFFnOkLkes-90n230ekjz6m4_5gebfKr0aKqU49TnKVpcEP_k875Ik_E2VcFVDOu4HzDFYRfCTv8Ogzd-tCUF5tXqwVY31X0M0_YNeuVKuH17uhfo5-dPq8UXvPx--3VxvcSaC8i4pdyCA0YaYpyu65p3xJla9FK2zFjXMcEa7uragXUgbdPyjnW8B25a5_qGXaD3x9xtDL8mm7La-NTbYdCjDVNSsgUQDPh_wUIJyWhbwA9HsI8hpWid2ka_Ka0VEHUYX_01fqEvT7FTt7HmmT2tXXx89H3Kdvds6_ioasmkUKsfd2p5u_gmiWDq0OfqyOs-qXWY4ljW--fnP6spmh0</recordid><startdate>19890801</startdate><enddate>19890801</enddate><creator>Gregory, Walter A</creator><creator>Brittelli, David R</creator><creator>Wang, C. L. J</creator><creator>Wuonola, Mark A</creator><creator>McRipley, Ronald J</creator><creator>Eustice, David C</creator><creator>Eberly, Virginia S</creator><creator>Slee, Andrew M</creator><creator>Forbes, Martin</creator><creator>Bartholomew, P. T</creator><general>American Chemical Society</general><scope>BSCLL</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>7QL</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>19890801</creationdate><title>Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group</title><author>Gregory, Walter A ; Brittelli, David R ; Wang, C. L. J ; Wuonola, Mark A ; McRipley, Ronald J ; Eustice, David C ; Eberly, Virginia S ; Slee, Andrew M ; Forbes, Martin ; Bartholomew, P. T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a451t-924e1f13080dfa6664b0fd65c7793defb35384f66f1ef17e894b3b4c14d9ffc83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1989</creationdate><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Enterococcus faecalis - drug effects</topic><topic>Escherichia coli - drug effects</topic><topic>Microbial Sensitivity Tests</topic><topic>Oxazoles - chemical synthesis</topic><topic>Oxazoles - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gregory, Walter A</creatorcontrib><creatorcontrib>Brittelli, David R</creatorcontrib><creatorcontrib>Wang, C. L. J</creatorcontrib><creatorcontrib>Wuonola, Mark A</creatorcontrib><creatorcontrib>McRipley, Ronald J</creatorcontrib><creatorcontrib>Eustice, David C</creatorcontrib><creatorcontrib>Eberly, Virginia S</creatorcontrib><creatorcontrib>Slee, Andrew M</creatorcontrib><creatorcontrib>Forbes, Martin</creatorcontrib><creatorcontrib>Bartholomew, P. T</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</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><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gregory, Walter A</au><au>Brittelli, David R</au><au>Wang, C. L. J</au><au>Wuonola, Mark A</au><au>McRipley, Ronald J</au><au>Eustice, David C</au><au>Eberly, Virginia S</au><au>Slee, Andrew M</au><au>Forbes, Martin</au><au>Bartholomew, P. T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1989-08-01</date><risdate>1989</risdate><volume>32</volume><issue>8</issue><spage>1673</spage><epage>1681</epage><pages>1673-1681</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>2502627</pmid><doi>10.1021/jm00128a003</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1989-08, Vol.32 (8), p.1673-1681 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_79115314 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - pharmacology Chemical Phenomena Chemistry Enterococcus faecalis - drug effects Escherichia coli - drug effects Microbial Sensitivity Tests Oxazoles - chemical synthesis Oxazoles - pharmacology Structure-Activity Relationship |
| title | Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-07T07%3A24%3A55IST&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=Antibacterials.%20Synthesis%20and%20structure-activity%20studies%20of%203-aryl-2-oxooxazolidines.%201.%20The%20B%20group&rft.jtitle=Journal%20of%20medicinal%20chemistry&rft.au=Gregory,%20Walter%20A&rft.date=1989-08-01&rft.volume=32&rft.issue=8&rft.spage=1673&rft.epage=1681&rft.pages=1673-1681&rft.issn=0022-2623&rft.eissn=1520-4804&rft_id=info:doi/10.1021/jm00128a003&rft_dat=%3Cproquest_cross%3E15357329%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=15357329&rft_id=info:pmid/2502627&rfr_iscdi=true |