Synthesis and Biological Activity of 2,3-Bis-(2-Oxoylidene)-1,2,3,4-Tetrahydroquinoxalines
Condensation of alkylmethylketones with diethyl oxalate and 1,2-diaminobenzene yielded 2,3- bis -(2-oxoylidene)-1,2,3,4-tetrahydroquinoxalines ( II – IV ). Four isomeric species were identified using spectral methods. Structural features of the synthesized compounds were discussed. The biological ac...
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| Veröffentlicht in: | Pharmaceutical chemistry journal 2015-01, Vol.48 (10), p.640-645 |
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| creator | Zykova, S. S. Odegova, T. F. Karmanova, O. G. Makhmudov, R. R. |
| description | Condensation of alkylmethylketones with diethyl oxalate and 1,2-diaminobenzene yielded 2,3-
bis
-(2-oxoylidene)-1,2,3,4-tetrahydroquinoxalines (
II
–
IV
). Four isomeric species were identified using spectral methods. Structural features of the synthesized compounds were discussed. The biological activity of the obtained compounds was investigated. It was observed that the synthesized compounds had low toxicity. It was found that (1
Z
,1′Z)-1,1′-(1,4-dihydroquinoxaline-2,3-diylidene)dibutan-2-one (
II
) exhibited antinociceptive activity that was greater than that of metamizole sodium. The antioxidant activity in an
Escherichia coli
BW 25113 oxidation resistance model in the presence of H
2
O
2
solution (3 mM) was also most pronounced for
II
whereas
V
had pro-oxidant activity. The compounds showed high antiradical activity for diphenylpicrylhydrazyl (DPPH) binding that was comparable with that of trolox. |
| doi_str_mv | 10.1007/s11094-015-1163-6 |
| format | Article |
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bis
-(2-oxoylidene)-1,2,3,4-tetrahydroquinoxalines (
II
–
IV
). Four isomeric species were identified using spectral methods. Structural features of the synthesized compounds were discussed. The biological activity of the obtained compounds was investigated. It was observed that the synthesized compounds had low toxicity. It was found that (1
Z
,1′Z)-1,1′-(1,4-dihydroquinoxaline-2,3-diylidene)dibutan-2-one (
II
) exhibited antinociceptive activity that was greater than that of metamizole sodium. The antioxidant activity in an
Escherichia coli
BW 25113 oxidation resistance model in the presence of H
2
O
2
solution (3 mM) was also most pronounced for
II
whereas
V
had pro-oxidant activity. The compounds showed high antiradical activity for diphenylpicrylhydrazyl (DPPH) binding that was comparable with that of trolox.</description><identifier>ISSN: 0091-150X</identifier><identifier>EISSN: 1573-9031</identifier><identifier>DOI: 10.1007/s11094-015-1163-6</identifier><language>eng</language><publisher>Boston: Springer US</publisher><subject>Analysis ; Antioxidants ; Medicine ; Organic Chemistry ; Oxalates ; Oxalic acid ; Pharmacology/Toxicology ; Pharmacy ; Search for New Drugs</subject><ispartof>Pharmaceutical chemistry journal, 2015-01, Vol.48 (10), p.640-645</ispartof><rights>Springer Science+Business Media New York 2015</rights><rights>COPYRIGHT 2015 Springer</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c377t-3588fa79a1e9c2bf9a0c12efcb1c0fc9e8ea06f4c8e91f024ccdb99d1d6c20723</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11094-015-1163-6$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11094-015-1163-6$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Zykova, S. S.</creatorcontrib><creatorcontrib>Odegova, T. F.</creatorcontrib><creatorcontrib>Karmanova, O. G.</creatorcontrib><creatorcontrib>Makhmudov, R. R.</creatorcontrib><title>Synthesis and Biological Activity of 2,3-Bis-(2-Oxoylidene)-1,2,3,4-Tetrahydroquinoxalines</title><title>Pharmaceutical chemistry journal</title><addtitle>Pharm Chem J</addtitle><description>Condensation of alkylmethylketones with diethyl oxalate and 1,2-diaminobenzene yielded 2,3-
bis
-(2-oxoylidene)-1,2,3,4-tetrahydroquinoxalines (
II
–
IV
). Four isomeric species were identified using spectral methods. Structural features of the synthesized compounds were discussed. The biological activity of the obtained compounds was investigated. It was observed that the synthesized compounds had low toxicity. It was found that (1
Z
,1′Z)-1,1′-(1,4-dihydroquinoxaline-2,3-diylidene)dibutan-2-one (
II
) exhibited antinociceptive activity that was greater than that of metamizole sodium. The antioxidant activity in an
Escherichia coli
BW 25113 oxidation resistance model in the presence of H
2
O
2
solution (3 mM) was also most pronounced for
II
whereas
V
had pro-oxidant activity. The compounds showed high antiradical activity for diphenylpicrylhydrazyl (DPPH) binding that was comparable with that of trolox.</description><subject>Analysis</subject><subject>Antioxidants</subject><subject>Medicine</subject><subject>Organic Chemistry</subject><subject>Oxalates</subject><subject>Oxalic acid</subject><subject>Pharmacology/Toxicology</subject><subject>Pharmacy</subject><subject>Search for New Drugs</subject><issn>0091-150X</issn><issn>1573-9031</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp9kE1LAzEQhoMoWD9-gLcFLwqNziT7lWMtfoHgQQXxEtJs0qZsE91sxf33ptSLIJLDQOZ9hpmHkBOECwSoLiMiiJwCFhSx5LTcISMsKk4FcNwlIwCBFAt43ScHMS4BEsXZiLw9Db5fmOhipnyTXbnQhrnTqs0munefrh-yYDM25vTKRXrG6ONXGFrXGG_OKY5TY5zTZ9N3ajE0XfhYOx--VOu8iUdkz6o2muOfekhebq6fp3f04fH2fjp5oJpXVU95UddWVUKhEZrNrFCgkRmrZ6jBamFqo6C0ua6NQAss17qZCdFgU2oGFeOH5HQ7d65aI523IW2jVy5qOcmhKliNOU-piz9S6TVm5XTwxrr0_wvALaC7EGNnrHzv3Ep1g0SQG-dy61wm53LjXJaJYVsmpqyfm04uw7rz6fp_oG9wiYJ5</recordid><startdate>20150101</startdate><enddate>20150101</enddate><creator>Zykova, S. S.</creator><creator>Odegova, T. F.</creator><creator>Karmanova, O. G.</creator><creator>Makhmudov, R. R.</creator><general>Springer US</general><general>Springer</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20150101</creationdate><title>Synthesis and Biological Activity of 2,3-Bis-(2-Oxoylidene)-1,2,3,4-Tetrahydroquinoxalines</title><author>Zykova, S. S. ; Odegova, T. F. ; Karmanova, O. G. ; Makhmudov, R. R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c377t-3588fa79a1e9c2bf9a0c12efcb1c0fc9e8ea06f4c8e91f024ccdb99d1d6c20723</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Analysis</topic><topic>Antioxidants</topic><topic>Medicine</topic><topic>Organic Chemistry</topic><topic>Oxalates</topic><topic>Oxalic acid</topic><topic>Pharmacology/Toxicology</topic><topic>Pharmacy</topic><topic>Search for New Drugs</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zykova, S. S.</creatorcontrib><creatorcontrib>Odegova, T. F.</creatorcontrib><creatorcontrib>Karmanova, O. G.</creatorcontrib><creatorcontrib>Makhmudov, R. R.</creatorcontrib><collection>CrossRef</collection><jtitle>Pharmaceutical chemistry journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zykova, S. S.</au><au>Odegova, T. F.</au><au>Karmanova, O. G.</au><au>Makhmudov, R. R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Biological Activity of 2,3-Bis-(2-Oxoylidene)-1,2,3,4-Tetrahydroquinoxalines</atitle><jtitle>Pharmaceutical chemistry journal</jtitle><stitle>Pharm Chem J</stitle><date>2015-01-01</date><risdate>2015</risdate><volume>48</volume><issue>10</issue><spage>640</spage><epage>645</epage><pages>640-645</pages><issn>0091-150X</issn><eissn>1573-9031</eissn><abstract>Condensation of alkylmethylketones with diethyl oxalate and 1,2-diaminobenzene yielded 2,3-
bis
-(2-oxoylidene)-1,2,3,4-tetrahydroquinoxalines (
II
–
IV
). Four isomeric species were identified using spectral methods. Structural features of the synthesized compounds were discussed. The biological activity of the obtained compounds was investigated. It was observed that the synthesized compounds had low toxicity. It was found that (1
Z
,1′Z)-1,1′-(1,4-dihydroquinoxaline-2,3-diylidene)dibutan-2-one (
II
) exhibited antinociceptive activity that was greater than that of metamizole sodium. The antioxidant activity in an
Escherichia coli
BW 25113 oxidation resistance model in the presence of H
2
O
2
solution (3 mM) was also most pronounced for
II
whereas
V
had pro-oxidant activity. The compounds showed high antiradical activity for diphenylpicrylhydrazyl (DPPH) binding that was comparable with that of trolox.</abstract><cop>Boston</cop><pub>Springer US</pub><doi>10.1007/s11094-015-1163-6</doi><tpages>6</tpages></addata></record> |
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| language | eng |
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| subjects | Analysis Antioxidants Medicine Organic Chemistry Oxalates Oxalic acid Pharmacology/Toxicology Pharmacy Search for New Drugs |
| title | Synthesis and Biological Activity of 2,3-Bis-(2-Oxoylidene)-1,2,3,4-Tetrahydroquinoxalines |
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