Synthesis and antimicrobial activity of pyranobenzoquinones related to the pyranonaphthoquinone antibiotics
The synthesis and antimicrobial activity of isochromane-type analogs of the pyranonaphthoquinone antibiotics are reported. Isochromane derivatives with ( 17a, b) and without ( 22a, b) a C-4 hydroxyl moiety and their corresponding quinones ( 19a and 23), were prepared. Both quinones exhibited antimic...
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| Veröffentlicht in: | European journal of medicinal chemistry 2006-11, Vol.41 (11), p.1333-1338 |
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| container_title | European journal of medicinal chemistry |
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| creator | Lagorio, S.H. Bianchi, D.A. Sutich, E.G. Kaufman, T.S. |
| description | The synthesis and antimicrobial activity of isochromane-type analogs of the pyranonaphthoquinone antibiotics are reported. Isochromane derivatives with (
17a,
b) and without (
22a,
b) a C-4 hydroxyl moiety and their corresponding quinones (
19a and
23), were prepared. Both quinones exhibited antimicrobial activity against
Staphylococcus aureus,
Bacillus atrophaeus and
Streptococcus agalactiae, while the related isochromanes were inactive. The results suggest that the quinone moiety is important for biological activity while the C-4 hydroxyl may not be essential.
Quinones were active regardless the presence of the alcohol moiety.
[Display omitted] |
| doi_str_mv | 10.1016/j.ejmech.2006.06.007 |
| format | Article |
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17a,
b) and without (
22a,
b) a C-4 hydroxyl moiety and their corresponding quinones (
19a and
23), were prepared. Both quinones exhibited antimicrobial activity against
Staphylococcus aureus,
Bacillus atrophaeus and
Streptococcus agalactiae, while the related isochromanes were inactive. The results suggest that the quinone moiety is important for biological activity while the C-4 hydroxyl may not be essential.
Quinones were active regardless the presence of the alcohol moiety.
[Display omitted]</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2006.06.007</identifier><identifier>PMID: 16889875</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antimicrobial activity ; Benzoquinones - chemical synthesis ; Benzoquinones - chemistry ; Benzoquinones - pharmacology ; Biological and medical sciences ; Chromans - chemical synthesis ; Chromans - chemistry ; Chromans - pharmacology ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Medical sciences ; Microbial Sensitivity Tests ; Pharmacology. Drug treatments ; Pyranobenzoquinones ; Pyranonaphthoquinone analogs ; Spectrophotometry, Infrared</subject><ispartof>European journal of medicinal chemistry, 2006-11, Vol.41 (11), p.1333-1338</ispartof><rights>2006 Elsevier Masson SAS</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c456t-c12395034c3a00c041d1150fb6d956466779489db7dd71a0d20caeb65be0e49a3</citedby><cites>FETCH-LOGICAL-c456t-c12395034c3a00c041d1150fb6d956466779489db7dd71a0d20caeb65be0e49a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2006.06.007$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27926,27927,45997</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18287665$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16889875$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lagorio, S.H.</creatorcontrib><creatorcontrib>Bianchi, D.A.</creatorcontrib><creatorcontrib>Sutich, E.G.</creatorcontrib><creatorcontrib>Kaufman, T.S.</creatorcontrib><title>Synthesis and antimicrobial activity of pyranobenzoquinones related to the pyranonaphthoquinone antibiotics</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>The synthesis and antimicrobial activity of isochromane-type analogs of the pyranonaphthoquinone antibiotics are reported. Isochromane derivatives with (
17a,
b) and without (
22a,
b) a C-4 hydroxyl moiety and their corresponding quinones (
19a and
23), were prepared. Both quinones exhibited antimicrobial activity against
Staphylococcus aureus,
Bacillus atrophaeus and
Streptococcus agalactiae, while the related isochromanes were inactive. The results suggest that the quinone moiety is important for biological activity while the C-4 hydroxyl may not be essential.
Quinones were active regardless the presence of the alcohol moiety.
[Display omitted]</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>Antimicrobial activity</subject><subject>Benzoquinones - chemical synthesis</subject><subject>Benzoquinones - chemistry</subject><subject>Benzoquinones - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Chromans - chemical synthesis</subject><subject>Chromans - chemistry</subject><subject>Chromans - pharmacology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyranobenzoquinones</subject><subject>Pyranonaphthoquinone analogs</subject><subject>Spectrophotometry, Infrared</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kM9q3DAQh0VJaTZJ36AEX9KbtyNbf-xLIIS2KQR6aHMWsjRmtdjSRtIGNk-zz7JPVpvdkFthYC7f78fMR8gXCksKVHxbL3E9olktKwCxnAfkB7KgUjRlXXF2RhZQVXXJq5qdk4uU1gDABcAnck5F07SN5AsS_ux8XmFyqdDeHvbaZzc6E0Pn9FBok92Ly7si9If9Zhe1Dx361_C8dT54TEXEQWe0RQ6H_VTzBnm9WeXVG1bMpZ0L2Zl0RT72ekj4-bQvydOP73_vH8rH3z9_3d89loZxkUtDq7rlUDNTawADjFpKOfSdsC0XTAgpW9a0tpPWSqrBVmA0doJ3CMhaXV-Sr8feTZzOwJTV6JLBYdAewzYp0VBKRdtOIDuC088pRezVJrpRx52ioGbRaq2OotUsWs0Dcopdn_q33Yj2PXQyOwE3J0Ano4d-0mJceueaqpFCzNztkcPJxovDqJJx6A1aF9FkZYP7_yX_AAjJpFk</recordid><startdate>20061101</startdate><enddate>20061101</enddate><creator>Lagorio, S.H.</creator><creator>Bianchi, D.A.</creator><creator>Sutich, E.G.</creator><creator>Kaufman, T.S.</creator><general>Elsevier Masson SAS</general><general>Elsevier</general><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>20061101</creationdate><title>Synthesis and antimicrobial activity of pyranobenzoquinones related to the pyranonaphthoquinone antibiotics</title><author>Lagorio, S.H. ; Bianchi, D.A. ; Sutich, E.G. ; Kaufman, T.S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c456t-c12395034c3a00c041d1150fb6d956466779489db7dd71a0d20caeb65be0e49a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</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>Antimicrobial activity</topic><topic>Benzoquinones - chemical synthesis</topic><topic>Benzoquinones - chemistry</topic><topic>Benzoquinones - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Chromans - chemical synthesis</topic><topic>Chromans - chemistry</topic><topic>Chromans - pharmacology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyranobenzoquinones</topic><topic>Pyranonaphthoquinone analogs</topic><topic>Spectrophotometry, Infrared</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lagorio, S.H.</creatorcontrib><creatorcontrib>Bianchi, D.A.</creatorcontrib><creatorcontrib>Sutich, E.G.</creatorcontrib><creatorcontrib>Kaufman, T.S.</creatorcontrib><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>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lagorio, S.H.</au><au>Bianchi, D.A.</au><au>Sutich, E.G.</au><au>Kaufman, T.S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and antimicrobial activity of pyranobenzoquinones related to the pyranonaphthoquinone antibiotics</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2006-11-01</date><risdate>2006</risdate><volume>41</volume><issue>11</issue><spage>1333</spage><epage>1338</epage><pages>1333-1338</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>The synthesis and antimicrobial activity of isochromane-type analogs of the pyranonaphthoquinone antibiotics are reported. Isochromane derivatives with (
17a,
b) and without (
22a,
b) a C-4 hydroxyl moiety and their corresponding quinones (
19a and
23), were prepared. Both quinones exhibited antimicrobial activity against
Staphylococcus aureus,
Bacillus atrophaeus and
Streptococcus agalactiae, while the related isochromanes were inactive. The results suggest that the quinone moiety is important for biological activity while the C-4 hydroxyl may not be essential.
Quinones were active regardless the presence of the alcohol moiety.
[Display omitted]</abstract><cop>Oxford</cop><pub>Elsevier Masson SAS</pub><pmid>16889875</pmid><doi>10.1016/j.ejmech.2006.06.007</doi><tpages>6</tpages></addata></record> |
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| ispartof | European journal of medicinal chemistry, 2006-11, Vol.41 (11), p.1333-1338 |
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| subjects | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Antimicrobial activity Benzoquinones - chemical synthesis Benzoquinones - chemistry Benzoquinones - pharmacology Biological and medical sciences Chromans - chemical synthesis Chromans - chemistry Chromans - pharmacology Magnetic Resonance Spectroscopy Mass Spectrometry Medical sciences Microbial Sensitivity Tests Pharmacology. Drug treatments Pyranobenzoquinones Pyranonaphthoquinone analogs Spectrophotometry, Infrared |
| title | Synthesis and antimicrobial activity of pyranobenzoquinones related to the pyranonaphthoquinone antibiotics |
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