Synthesis and Antimycobacterial Activity of Pyrazine and Quinoxaline Derivatives
A series of pyrazine and quinoxaline derivatives have been synthesized, and their activity against M. tuberculosis (Mtb) and Mycobacterium avium (MAC) are reported. The 4-acetoxybenzyl ester of pyrazinoic acid and 4‘-acetoxybenzyl 2-quinoxalinecarboxylate showed excellent activity against Mtb (MIC r...
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| Veröffentlicht in: | Journal of medicinal chemistry 2002-12, Vol.45 (25), p.5604-5606 |
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| container_end_page | 5606 |
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| container_issue | 25 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 45 |
| creator | Seitz, Lainne E Suling, William J Reynolds, Robert C |
| description | A series of pyrazine and quinoxaline derivatives have been synthesized, and their activity against M. tuberculosis (Mtb) and Mycobacterium avium (MAC) are reported. The 4-acetoxybenzyl ester of pyrazinoic acid and 4‘-acetoxybenzyl 2-quinoxalinecarboxylate showed excellent activity against Mtb (MIC ranges of less than 1−6.25 μg/mL) but only modest activity against MAC (MICs of 4−32 μg/mL). |
| doi_str_mv | 10.1021/jm020310n |
| format | Article |
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The 4-acetoxybenzyl ester of pyrazinoic acid and 4‘-acetoxybenzyl 2-quinoxalinecarboxylate showed excellent activity against Mtb (MIC ranges of less than 1−6.25 μg/mL) but only modest activity against MAC (MICs of 4−32 μg/mL).</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm020310n</identifier><identifier>PMID: 12459027</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Biological and medical sciences ; Medical sciences ; Microbial Sensitivity Tests ; Mycobacterium avium - drug effects ; Mycobacterium tuberculosis - drug effects ; Pharmacology. Drug treatments ; Pyrazinamide - analogs & derivatives ; Pyrazinamide - chemical synthesis ; Pyrazinamide - chemistry ; Pyrazinamide - pharmacology ; Pyrazines - chemical synthesis ; Pyrazines - chemistry ; Pyrazines - pharmacology ; Quinoxalines - chemical synthesis ; Quinoxalines - chemistry ; Quinoxalines - pharmacology ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2002-12, Vol.45 (25), p.5604-5606</ispartof><rights>Copyright © 2002 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-812b06bb779c77059a92afaec9d005899ee3e9f313ac90408c60c0d6a4e817933</citedby><cites>FETCH-LOGICAL-a445t-812b06bb779c77059a92afaec9d005899ee3e9f313ac90408c60c0d6a4e817933</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm020310n$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm020310n$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14924720$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12459027$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Seitz, Lainne E</creatorcontrib><creatorcontrib>Suling, William J</creatorcontrib><creatorcontrib>Reynolds, Robert C</creatorcontrib><title>Synthesis and Antimycobacterial Activity of Pyrazine and Quinoxaline Derivatives</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of pyrazine and quinoxaline derivatives have been synthesized, and their activity against M. tuberculosis (Mtb) and Mycobacterium avium (MAC) are reported. The 4-acetoxybenzyl ester of pyrazinoic acid and 4‘-acetoxybenzyl 2-quinoxalinecarboxylate showed excellent activity against Mtb (MIC ranges of less than 1−6.25 μg/mL) but only modest activity against MAC (MICs of 4−32 μg/mL).</description><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Biological and medical sciences</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Mycobacterium avium - drug effects</subject><subject>Mycobacterium tuberculosis - drug effects</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyrazinamide - analogs & derivatives</subject><subject>Pyrazinamide - chemical synthesis</subject><subject>Pyrazinamide - chemistry</subject><subject>Pyrazinamide - pharmacology</subject><subject>Pyrazines - chemical synthesis</subject><subject>Pyrazines - chemistry</subject><subject>Pyrazines - pharmacology</subject><subject>Quinoxalines - chemical synthesis</subject><subject>Quinoxalines - chemistry</subject><subject>Quinoxalines - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1P3DAQBmALtYJl4dA_gHKhEoe044_E8XFFy4dYlUV8qDdr4nWEl8ShdoJIfz2hu2IvPY1G8-jV6CXkC4VvFBj9vmqAAafgd8iEZgxSUYD4RCYAjKUsZ3yP7Me4AhgR47tkjzKRKWByQha3g-8ebXQxQb9MZr5zzWDaEk1ng8M6mZnOvbhuSNoqWQwB_zpv_9Gb3vn2Fev3_cdoX3CENh6QzxXW0R5u5pTcn_28O71I59fnl6ezeYpCZF1aUFZCXpZSKiMlZAoVwwqtUUuArFDKWm5VxSlHo0BAYXIwsMxR2IJKxfmUfF3nPof2T29jpxsXja1r9Lbto5ZMcqEEHeHJGprQxhhspZ-DazAMmoJ-r09_1Dfao01oXzZ2uZWbvkZwvAEYDdZVQG9c3DqhmJBj2JSka-diZ18_7hiedC65zPTd4lY_nF3Nfwn6W19tc9FEvWr74Mfu_vPgGy2kkog</recordid><startdate>20021205</startdate><enddate>20021205</enddate><creator>Seitz, Lainne E</creator><creator>Suling, William J</creator><creator>Reynolds, Robert C</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>20021205</creationdate><title>Synthesis and Antimycobacterial Activity of Pyrazine and Quinoxaline Derivatives</title><author>Seitz, Lainne E ; Suling, William J ; Reynolds, Robert C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-812b06bb779c77059a92afaec9d005899ee3e9f313ac90408c60c0d6a4e817933</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Biological and medical sciences</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Mycobacterium avium - drug effects</topic><topic>Mycobacterium tuberculosis - drug effects</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyrazinamide - analogs & derivatives</topic><topic>Pyrazinamide - chemical synthesis</topic><topic>Pyrazinamide - chemistry</topic><topic>Pyrazinamide - pharmacology</topic><topic>Pyrazines - chemical synthesis</topic><topic>Pyrazines - chemistry</topic><topic>Pyrazines - pharmacology</topic><topic>Quinoxalines - chemical synthesis</topic><topic>Quinoxalines - chemistry</topic><topic>Quinoxalines - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Seitz, Lainne E</creatorcontrib><creatorcontrib>Suling, William J</creatorcontrib><creatorcontrib>Reynolds, Robert C</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>Seitz, Lainne E</au><au>Suling, William J</au><au>Reynolds, Robert C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Antimycobacterial Activity of Pyrazine and Quinoxaline Derivatives</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2002-12-05</date><risdate>2002</risdate><volume>45</volume><issue>25</issue><spage>5604</spage><epage>5606</epage><pages>5604-5606</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>A series of pyrazine and quinoxaline derivatives have been synthesized, and their activity against M. tuberculosis (Mtb) and Mycobacterium avium (MAC) are reported. The 4-acetoxybenzyl ester of pyrazinoic acid and 4‘-acetoxybenzyl 2-quinoxalinecarboxylate showed excellent activity against Mtb (MIC ranges of less than 1−6.25 μg/mL) but only modest activity against MAC (MICs of 4−32 μg/mL).</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12459027</pmid><doi>10.1021/jm020310n</doi><tpages>3</tpages></addata></record> |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Biological and medical sciences Medical sciences Microbial Sensitivity Tests Mycobacterium avium - drug effects Mycobacterium tuberculosis - drug effects Pharmacology. Drug treatments Pyrazinamide - analogs & derivatives Pyrazinamide - chemical synthesis Pyrazinamide - chemistry Pyrazinamide - pharmacology Pyrazines - chemical synthesis Pyrazines - chemistry Pyrazines - pharmacology Quinoxalines - chemical synthesis Quinoxalines - chemistry Quinoxalines - pharmacology Structure-Activity Relationship |
| title | Synthesis and Antimycobacterial Activity of Pyrazine and Quinoxaline Derivatives |
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