Preparation and antibacterial activities of new 1,2,3-diazaborine derivatives and analogs
1,2-Dihydro-1-hydroxy-2-(organosulfonyl)areno[d] [1,2,3]diazaborines 2 (arene = benzene, naphthalene, thiophene, furan, pyrrole) were synthesized by reaction of (organosulfonyl)hydrazones of arene aldehydes or ketones with tribromoborane in the presence of ferric chloride. The activities of 2 agains...
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| Veröffentlicht in: | Journal of medicinal chemistry 1984-08, Vol.27 (8), p.947-953 |
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| container_title | Journal of medicinal chemistry |
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| creator | Grassberger, Maximilian A Turnowsky, Friederike Hildebrandt, Johannes |
| description | 1,2-Dihydro-1-hydroxy-2-(organosulfonyl)areno[d] [1,2,3]diazaborines 2 (arene = benzene, naphthalene, thiophene, furan, pyrrole) were synthesized by reaction of (organosulfonyl)hydrazones of arene aldehydes or ketones with tribromoborane in the presence of ferric chloride. The activities of 2 against bacteria in vitro and in vivo (Escherichia coli) were determined and structure-activity relationships are discussed. Included in this study are 2,3-dihydro-1-hydroxy-2-(p-tolylsulfonyl)-1H-2,1-benzazaborole+ ++ (3) and 1-hydroxy-1,2,3,4-tetrahydro-2-(p-tolylsulfonyl)-2,1-benzazabor ine (4) as well as the carbacyclic benzodiazaborine analogue 4-hydroxy-3-(p-tolylsulfonyl)isoquinoline (7). The nature of the active species is briefly discussed. |
| doi_str_mv | 10.1021/jm00374a003 |
| format | Article |
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The activities of 2 against bacteria in vitro and in vivo (Escherichia coli) were determined and structure-activity relationships are discussed. Included in this study are 2,3-dihydro-1-hydroxy-2-(p-tolylsulfonyl)-1H-2,1-benzazaborole+ ++ (3) and 1-hydroxy-1,2,3,4-tetrahydro-2-(p-tolylsulfonyl)-2,1-benzazabor ine (4) as well as the carbacyclic benzodiazaborine analogue 4-hydroxy-3-(p-tolylsulfonyl)isoquinoline (7). The nature of the active species is briefly discussed.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00374a003</identifier><identifier>PMID: 6379179</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Anti-Bacterial Agents - chemical synthesis ; B derivatives ; Boron Compounds - chemical synthesis ; Boron Compounds - pharmacology ; Chemistry ; Escherichia coli ; Escherichia coli - drug effects ; Exact sciences and technology ; Gram-Negative Bacteria - drug effects ; Organic chemistry ; Organometalloidal and organometallic compounds ; Preparations and properties ; Structure-Activity Relationship ; Sulfones - chemical synthesis ; Sulfones - pharmacology</subject><ispartof>Journal of medicinal chemistry, 1984-08, Vol.27 (8), p.947-953</ispartof><rights>1984 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a414t-77cb1f7a19dd26100e5b67006e22efd280fe30c957c19072cbe2bc8a91d64e623</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/jm00374a003$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00374a003$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=9672057$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6379179$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Grassberger, Maximilian A</creatorcontrib><creatorcontrib>Turnowsky, Friederike</creatorcontrib><creatorcontrib>Hildebrandt, Johannes</creatorcontrib><title>Preparation and antibacterial activities of new 1,2,3-diazaborine derivatives and analogs</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>1,2-Dihydro-1-hydroxy-2-(organosulfonyl)areno[d] [1,2,3]diazaborines 2 (arene = benzene, naphthalene, thiophene, furan, pyrrole) were synthesized by reaction of (organosulfonyl)hydrazones of arene aldehydes or ketones with tribromoborane in the presence of ferric chloride. The activities of 2 against bacteria in vitro and in vivo (Escherichia coli) were determined and structure-activity relationships are discussed. Included in this study are 2,3-dihydro-1-hydroxy-2-(p-tolylsulfonyl)-1H-2,1-benzazaborole+ ++ (3) and 1-hydroxy-1,2,3,4-tetrahydro-2-(p-tolylsulfonyl)-2,1-benzazabor ine (4) as well as the carbacyclic benzodiazaborine analogue 4-hydroxy-3-(p-tolylsulfonyl)isoquinoline (7). The nature of the active species is briefly discussed.</description><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>B derivatives</subject><subject>Boron Compounds - chemical synthesis</subject><subject>Boron Compounds - pharmacology</subject><subject>Chemistry</subject><subject>Escherichia coli</subject><subject>Escherichia coli - drug effects</subject><subject>Exact sciences and technology</subject><subject>Gram-Negative Bacteria - drug effects</subject><subject>Organic chemistry</subject><subject>Organometalloidal and organometallic compounds</subject><subject>Preparations and properties</subject><subject>Structure-Activity Relationship</subject><subject>Sulfones - chemical synthesis</subject><subject>Sulfones - pharmacology</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1984</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0MGL1DAUBvAgyjqunjwLPYge3Op7aZs0R1l3dWHBAVdQL-E1fZWMnXZMOuPu_vVm6TDsQfCQpPB-fGk-IZ4jvEWQ-G61Bih0SWl_IBZYScjLGsqHYgEgZS6VLB6LJzGuIAmUxZE4UoU2qM1CfF8G3lCgyY9DRkOb1uQbchMHT32WPvzOT55jNnbZwH8yPJEnRd56uqVmDH7grE10lwJ2Cc0J1I8_41PxqKM-8rP9eSy-np9dnX7KLz9_vDh9f5lTieWUa-0a7DShaVupEICrRmkAxVJy18oaOi7AmUo7NKCla1g2riaDrSo5Pe1YvJpzN2H8veU42bWPjvueBh630daIujZY_RdiYZTEWif4ZoYujDEG7uwm-DWFG4tg7xq39xpP-sU-dtusuT3YfcVp_nI_p-io7wINzscDM0pLqO4uzWfm48TXhzGFX1bpQlf2avnFqmXxQ36Q5_Zb8q9nTy7a1bgNqfX4zx_8C0gNouY</recordid><startdate>198408</startdate><enddate>198408</enddate><creator>Grassberger, Maximilian A</creator><creator>Turnowsky, Friederike</creator><creator>Hildebrandt, Johannes</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</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>198408</creationdate><title>Preparation and antibacterial activities of new 1,2,3-diazaborine derivatives and analogs</title><author>Grassberger, Maximilian A ; Turnowsky, Friederike ; Hildebrandt, Johannes</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a414t-77cb1f7a19dd26100e5b67006e22efd280fe30c957c19072cbe2bc8a91d64e623</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1984</creationdate><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>B derivatives</topic><topic>Boron Compounds - chemical synthesis</topic><topic>Boron Compounds - pharmacology</topic><topic>Chemistry</topic><topic>Escherichia coli</topic><topic>Escherichia coli - drug effects</topic><topic>Exact sciences and technology</topic><topic>Gram-Negative Bacteria - drug effects</topic><topic>Organic chemistry</topic><topic>Organometalloidal and organometallic compounds</topic><topic>Preparations and properties</topic><topic>Structure-Activity Relationship</topic><topic>Sulfones - chemical synthesis</topic><topic>Sulfones - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Grassberger, Maximilian A</creatorcontrib><creatorcontrib>Turnowsky, Friederike</creatorcontrib><creatorcontrib>Hildebrandt, Johannes</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</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>Grassberger, Maximilian A</au><au>Turnowsky, Friederike</au><au>Hildebrandt, Johannes</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation and antibacterial activities of new 1,2,3-diazaborine derivatives and analogs</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1984-08</date><risdate>1984</risdate><volume>27</volume><issue>8</issue><spage>947</spage><epage>953</epage><pages>947-953</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>1,2-Dihydro-1-hydroxy-2-(organosulfonyl)areno[d] [1,2,3]diazaborines 2 (arene = benzene, naphthalene, thiophene, furan, pyrrole) were synthesized by reaction of (organosulfonyl)hydrazones of arene aldehydes or ketones with tribromoborane in the presence of ferric chloride. The activities of 2 against bacteria in vitro and in vivo (Escherichia coli) were determined and structure-activity relationships are discussed. Included in this study are 2,3-dihydro-1-hydroxy-2-(p-tolylsulfonyl)-1H-2,1-benzazaborole+ ++ (3) and 1-hydroxy-1,2,3,4-tetrahydro-2-(p-tolylsulfonyl)-2,1-benzazabor ine (4) as well as the carbacyclic benzodiazaborine analogue 4-hydroxy-3-(p-tolylsulfonyl)isoquinoline (7). The nature of the active species is briefly discussed.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>6379179</pmid><doi>10.1021/jm00374a003</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1984-08, Vol.27 (8), p.947-953 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Anti-Bacterial Agents - chemical synthesis B derivatives Boron Compounds - chemical synthesis Boron Compounds - pharmacology Chemistry Escherichia coli Escherichia coli - drug effects Exact sciences and technology Gram-Negative Bacteria - drug effects Organic chemistry Organometalloidal and organometallic compounds Preparations and properties Structure-Activity Relationship Sulfones - chemical synthesis Sulfones - pharmacology |
| title | Preparation and antibacterial activities of new 1,2,3-diazaborine derivatives and analogs |
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