Aromatic esters of 5-O-desosaminylerythronolide A oxime
Several substituted aromatic esters of the C-3 hydroxyl of 5-O-desosaminylerythronolide A oxime were prepared. Ribosomal binding studies showed that meta substituents on the aromatic ring gave the most active analogs. The esters described were all inactive in vivo at the maximum level tested.
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| Veröffentlicht in: | Journal of medicinal chemistry 1975-08, Vol.18 (8), p.849-851 |
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| container_end_page | 851 |
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| container_issue | 8 |
| container_start_page | 849 |
| container_title | Journal of medicinal chemistry |
| container_volume | 18 |
| creator | LeMahieu, Ronald A Carson, Mathew Kierstead, Richard W Pestka, Sidney |
| description | Several substituted aromatic esters of the C-3 hydroxyl of 5-O-desosaminylerythronolide A oxime were prepared. Ribosomal binding studies showed that meta substituents on the aromatic ring gave the most active analogs. The esters described were all inactive in vivo at the maximum level tested. |
| doi_str_mv | 10.1021/jm00242a020 |
| format | Article |
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Ribosomal binding studies showed that meta substituents on the aromatic ring gave the most active analogs. The esters described were all inactive in vivo at the maximum level tested.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00242a020</identifier><identifier>PMID: 808612</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Bacillus subtilis - drug effects ; Erythromycin - analogs & derivatives ; Erythromycin - chemical synthesis ; Erythromycin - pharmacology ; Erythromycin - therapeutic use ; Escherichia coli - drug effects ; Escherichia coli - metabolism ; Oximes - chemical synthesis ; Oximes - pharmacology ; Oximes - therapeutic use ; Proteus Infections - drug therapy ; Proteus vulgaris ; Pseudomonas aeruginosa - drug effects ; Ribosomes - metabolism ; Saccharomyces cerevisiae - drug effects ; Staphylococcal Infections - drug therapy ; Staphylococcus - drug effects ; Streptococcal Infections - drug therapy ; Streptococcus pyogenes</subject><ispartof>Journal of medicinal chemistry, 1975-08, Vol.18 (8), p.849-851</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a334t-8ca1048d0bc9398bf226b316d3700c5219200cc93d1001131f6b040ac50cebf3</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/jm00242a020$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00242a020$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27074,27922,27923,56736,56786</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/808612$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>LeMahieu, Ronald A</creatorcontrib><creatorcontrib>Carson, Mathew</creatorcontrib><creatorcontrib>Kierstead, Richard W</creatorcontrib><creatorcontrib>Pestka, Sidney</creatorcontrib><title>Aromatic esters of 5-O-desosaminylerythronolide A oxime</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Several substituted aromatic esters of the C-3 hydroxyl of 5-O-desosaminylerythronolide A oxime were prepared. Ribosomal binding studies showed that meta substituents on the aromatic ring gave the most active analogs. The esters described were all inactive in vivo at the maximum level tested.</description><subject>Bacillus subtilis - drug effects</subject><subject>Erythromycin - analogs & derivatives</subject><subject>Erythromycin - chemical synthesis</subject><subject>Erythromycin - pharmacology</subject><subject>Erythromycin - therapeutic use</subject><subject>Escherichia coli - drug effects</subject><subject>Escherichia coli - metabolism</subject><subject>Oximes - chemical synthesis</subject><subject>Oximes - pharmacology</subject><subject>Oximes - therapeutic use</subject><subject>Proteus Infections - drug therapy</subject><subject>Proteus vulgaris</subject><subject>Pseudomonas aeruginosa - drug effects</subject><subject>Ribosomes - metabolism</subject><subject>Saccharomyces cerevisiae - drug effects</subject><subject>Staphylococcal Infections - drug therapy</subject><subject>Staphylococcus - drug effects</subject><subject>Streptococcal Infections - drug therapy</subject><subject>Streptococcus pyogenes</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1975</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkD1PwzAQhi3EVylMrAyZYECG8zmfY1UBRVQUiU4sluM4IiWJi51I7b_HKFXFwHTSvY_eOz2EXDK4Y4DsftUAYIgSEA7IiEUINEwhPCQjv0eKMfJTcubcCgA4Q35CjlNIY4YjkkysaWRXqUC7TlsXmDKI6IIW2hknm6rd1tpuu09rWlNXhQ4mgdlUjT4nR6Wsnb7YzTFZPj4spzM6Xzw9TydzKjkPO5oqySBMC8hVxrM0LxHjnLO44AmAipBl6KfPCgbAGGdlnEMIUkWgdF7yMbkeatfWfPf-RdFUTum6lq02vRMpZmmUxJkHbwdQWeOc1aVY26qRdisYiF9J4o8kT1_tavu80cWeHaz4mA5x5Z1s9qm0XyJOeBKJ5du7mL984GsWcTHz_M3AS-XEyvS29Ur-PfwDDt97OA</recordid><startdate>19750801</startdate><enddate>19750801</enddate><creator>LeMahieu, Ronald A</creator><creator>Carson, Mathew</creator><creator>Kierstead, Richard W</creator><creator>Pestka, Sidney</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>7X8</scope></search><sort><creationdate>19750801</creationdate><title>Aromatic esters of 5-O-desosaminylerythronolide A oxime</title><author>LeMahieu, Ronald A ; Carson, Mathew ; Kierstead, Richard W ; Pestka, Sidney</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a334t-8ca1048d0bc9398bf226b316d3700c5219200cc93d1001131f6b040ac50cebf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1975</creationdate><topic>Bacillus subtilis - drug effects</topic><topic>Erythromycin - analogs & derivatives</topic><topic>Erythromycin - chemical synthesis</topic><topic>Erythromycin - pharmacology</topic><topic>Erythromycin - therapeutic use</topic><topic>Escherichia coli - drug effects</topic><topic>Escherichia coli - metabolism</topic><topic>Oximes - chemical synthesis</topic><topic>Oximes - pharmacology</topic><topic>Oximes - therapeutic use</topic><topic>Proteus Infections - drug therapy</topic><topic>Proteus vulgaris</topic><topic>Pseudomonas aeruginosa - drug effects</topic><topic>Ribosomes - metabolism</topic><topic>Saccharomyces cerevisiae - drug effects</topic><topic>Staphylococcal Infections - drug therapy</topic><topic>Staphylococcus - drug effects</topic><topic>Streptococcal Infections - drug therapy</topic><topic>Streptococcus pyogenes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>LeMahieu, Ronald A</creatorcontrib><creatorcontrib>Carson, Mathew</creatorcontrib><creatorcontrib>Kierstead, Richard W</creatorcontrib><creatorcontrib>Pestka, Sidney</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>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>LeMahieu, Ronald A</au><au>Carson, Mathew</au><au>Kierstead, Richard W</au><au>Pestka, Sidney</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Aromatic esters of 5-O-desosaminylerythronolide A oxime</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. 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| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1975-08, Vol.18 (8), p.849-851 |
| issn | 0022-2623 1520-4804 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Bacillus subtilis - drug effects Erythromycin - analogs & derivatives Erythromycin - chemical synthesis Erythromycin - pharmacology Erythromycin - therapeutic use Escherichia coli - drug effects Escherichia coli - metabolism Oximes - chemical synthesis Oximes - pharmacology Oximes - therapeutic use Proteus Infections - drug therapy Proteus vulgaris Pseudomonas aeruginosa - drug effects Ribosomes - metabolism Saccharomyces cerevisiae - drug effects Staphylococcal Infections - drug therapy Staphylococcus - drug effects Streptococcal Infections - drug therapy Streptococcus pyogenes |
| title | Aromatic esters of 5-O-desosaminylerythronolide A oxime |
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