An examination of O-2-isocephems as orally absorbable antibiotics
The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-is...
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| Veröffentlicht in: | Journal of medicinal chemistry 1988-06, Vol.31 (6), p.1190-1196 |
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| container_end_page | 1196 |
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| container_issue | 6 |
| container_start_page | 1190 |
| container_title | Journal of medicinal chemistry |
| container_volume | 31 |
| creator | Mastalerz, Harold Menard, Marcel Vinet, Vivianne Desiderio, James Fung-Tomc, Joan Kessler, Robert Tsai, Yuan |
| description | The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries. |
| doi_str_mv | 10.1021/jm00401a020 |
| format | Article |
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These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. 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Med. Chem</addtitle><description>The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.</description><subject>Administration, Oral</subject><subject>Cephalosporins - chemical synthesis</subject><subject>Cephalosporins - pharmacokinetics</subject><subject>Cephalosporins - pharmacology</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Microbial Sensitivity Tests</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0EtLHEEUBeAiRHQ0WWUt9CLoQjq59eiumuVg4igoCpl9cetFauzuGqt6QP99OswwuHB1F-fjcDmEfKPwgwKjP9c9gACKwOATmdGGQS0UiM9kBsBYzVrGT8hpKWsA4JTxY3LMueRCqRlZLIbKv2IfBxxjGqoUqsea1bEk6zd_fV8qLFXK2HVvFZqSskHT-QqHMZqYxmjLF3IUsCv-6_6ekdXN79X1bX3_uLy7XtzXyBUfa48SGqO4CmYuwxxaJ8AF2srgXPDCCUrBKeqNkcYxpOhs44QK3HkVpOVn5GJXu8npZevLqPtYrO86HHzaFi0VEyAlTPBqB21OpWQf9CbHHvObpqD_76Xf7TXp833t1vTeHex-oCn_vs-xWOxCxsHGcmCSNq1QYmL1jsUy-tdDjPlZt5LLRq-e_ujlr4d2_rRq9HLylzuPtuh12uZhmu7DB_8BRFGNxA</recordid><startdate>19880601</startdate><enddate>19880601</enddate><creator>Mastalerz, Harold</creator><creator>Menard, Marcel</creator><creator>Vinet, Vivianne</creator><creator>Desiderio, James</creator><creator>Fung-Tomc, Joan</creator><creator>Kessler, Robert</creator><creator>Tsai, Yuan</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>7X8</scope></search><sort><creationdate>19880601</creationdate><title>An examination of O-2-isocephems as orally absorbable antibiotics</title><author>Mastalerz, Harold ; Menard, Marcel ; Vinet, Vivianne ; Desiderio, James ; Fung-Tomc, Joan ; Kessler, Robert ; Tsai, Yuan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a383t-ea705b838fb97f906d40df167fddfe4d4110d81ebb7bd2a1adc5d48f3de8f7c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>Administration, Oral</topic><topic>Cephalosporins - chemical synthesis</topic><topic>Cephalosporins - pharmacokinetics</topic><topic>Cephalosporins - pharmacology</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Microbial Sensitivity Tests</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mastalerz, Harold</creatorcontrib><creatorcontrib>Menard, Marcel</creatorcontrib><creatorcontrib>Vinet, Vivianne</creatorcontrib><creatorcontrib>Desiderio, James</creatorcontrib><creatorcontrib>Fung-Tomc, Joan</creatorcontrib><creatorcontrib>Kessler, Robert</creatorcontrib><creatorcontrib>Tsai, Yuan</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>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mastalerz, Harold</au><au>Menard, Marcel</au><au>Vinet, Vivianne</au><au>Desiderio, James</au><au>Fung-Tomc, Joan</au><au>Kessler, Robert</au><au>Tsai, Yuan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An examination of O-2-isocephems as orally absorbable antibiotics</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1988-06-01</date><risdate>1988</risdate><volume>31</volume><issue>6</issue><spage>1190</spage><epage>1196</epage><pages>1190-1196</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>3373488</pmid><doi>10.1021/jm00401a020</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1988-06, Vol.31 (6), p.1190-1196 |
| issn | 0022-2623 1520-4804 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Administration, Oral Cephalosporins - chemical synthesis Cephalosporins - pharmacokinetics Cephalosporins - pharmacology Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Microbial Sensitivity Tests Organic chemistry Preparations and properties Structure-Activity Relationship |
| title | An examination of O-2-isocephems as orally absorbable antibiotics |
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