Synthesis, antibacterial and cytotoxic activities of new biflorin-based hydrazones and oximes
[Display omitted] Biflorin 1 is a biologically active quinone, isolated from Capraria biflora. Five new biflorin-based nitrogen derivatives were synthesized, of which two were mixtures of (E)- and (Z)- isomers: (Z)-2a, (Z)-2b, (Z)-3a, (Z)- and (E)-3b, (Z)- and (E)-3c. The antibacterial activity was...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2016-01, Vol.26 (2), p.435-439 |
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| creator | da S. Souza, Luciana G. Almeida, Macia C.S. Lemos, Telma L.G. Ribeiro, Paulo R.V. de Brito, Edy S. Silva, Vera L.M. Silva, Artur M.S. Braz-Filho, Raimundo Costa, José G.M. Rodrigues, Fábio F.G. Barreto, Francisco S. de Moraes, Manoel O. |
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Biflorin 1 is a biologically active quinone, isolated from Capraria biflora. Five new biflorin-based nitrogen derivatives were synthesized, of which two were mixtures of (E)- and (Z)- isomers: (Z)-2a, (Z)-2b, (Z)-3a, (Z)- and (E)-3b, (Z)- and (E)-3c. The antibacterial activity was investigated using the microdilution method for determining the minimum inhibitory concentration (MIC) against six bacterial strains. Tests have shown that these derivatives have potential against all bacterial strains. The cytotoxic activity was also evaluated against three strains of cancer cells, but none of the derivatives showed activity. |
| doi_str_mv | 10.1016/j.bmcl.2015.11.095 |
| format | Article |
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Biflorin 1 is a biologically active quinone, isolated from Capraria biflora. Five new biflorin-based nitrogen derivatives were synthesized, of which two were mixtures of (E)- and (Z)- isomers: (Z)-2a, (Z)-2b, (Z)-3a, (Z)- and (E)-3b, (Z)- and (E)-3c. The antibacterial activity was investigated using the microdilution method for determining the minimum inhibitory concentration (MIC) against six bacterial strains. Tests have shown that these derivatives have potential against all bacterial strains. The cytotoxic activity was also evaluated against three strains of cancer cells, but none of the derivatives showed activity.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2015.11.095</identifier><identifier>PMID: 26684850</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibacterial ; Antineoplastic Agents, Phytogenic - chemical synthesis ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - pharmacology ; Antitumoral ; Bacteria - drug effects ; Bacterial Infections - drug therapy ; Biflorin ; Cell Line, Tumor ; Humans ; Hydrazones ; Hydrazones - chemical synthesis ; Hydrazones - chemistry ; Hydrazones - pharmacology ; Microbial Sensitivity Tests ; Naphthoquinones - chemical synthesis ; Naphthoquinones - chemistry ; Naphthoquinones - pharmacology ; Neoplasms - drug therapy ; Oximes ; Oximes - chemical synthesis ; Oximes - chemistry ; Oximes - pharmacology ; Scrophulariaceae - chemistry</subject><ispartof>Bioorganic & medicinal chemistry letters, 2016-01, Vol.26 (2), p.435-439</ispartof><rights>2015</rights><rights>Copyright © 2015. Published by Elsevier Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-361379481b3d4a5ecdb1ae66154083bb1d872b59f17578ebee753a9339b18f903</citedby><cites>FETCH-LOGICAL-c356t-361379481b3d4a5ecdb1ae66154083bb1d872b59f17578ebee753a9339b18f903</cites><orcidid>0000-0003-4084-8076</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X15303036$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26684850$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>da S. Souza, Luciana G.</creatorcontrib><creatorcontrib>Almeida, Macia C.S.</creatorcontrib><creatorcontrib>Lemos, Telma L.G.</creatorcontrib><creatorcontrib>Ribeiro, Paulo R.V.</creatorcontrib><creatorcontrib>de Brito, Edy S.</creatorcontrib><creatorcontrib>Silva, Vera L.M.</creatorcontrib><creatorcontrib>Silva, Artur M.S.</creatorcontrib><creatorcontrib>Braz-Filho, Raimundo</creatorcontrib><creatorcontrib>Costa, José G.M.</creatorcontrib><creatorcontrib>Rodrigues, Fábio F.G.</creatorcontrib><creatorcontrib>Barreto, Francisco S.</creatorcontrib><creatorcontrib>de Moraes, Manoel O.</creatorcontrib><title>Synthesis, antibacterial and cytotoxic activities of new biflorin-based hydrazones and oximes</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
Biflorin 1 is a biologically active quinone, isolated from Capraria biflora. Five new biflorin-based nitrogen derivatives were synthesized, of which two were mixtures of (E)- and (Z)- isomers: (Z)-2a, (Z)-2b, (Z)-3a, (Z)- and (E)-3b, (Z)- and (E)-3c. The antibacterial activity was investigated using the microdilution method for determining the minimum inhibitory concentration (MIC) against six bacterial strains. Tests have shown that these derivatives have potential against all bacterial strains. The cytotoxic activity was also evaluated against three strains of cancer cells, but none of the derivatives showed activity.</description><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial</subject><subject>Antineoplastic Agents, Phytogenic - chemical synthesis</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Antitumoral</subject><subject>Bacteria - drug effects</subject><subject>Bacterial Infections - drug therapy</subject><subject>Biflorin</subject><subject>Cell Line, Tumor</subject><subject>Humans</subject><subject>Hydrazones</subject><subject>Hydrazones - chemical synthesis</subject><subject>Hydrazones - chemistry</subject><subject>Hydrazones - pharmacology</subject><subject>Microbial Sensitivity Tests</subject><subject>Naphthoquinones - chemical synthesis</subject><subject>Naphthoquinones - chemistry</subject><subject>Naphthoquinones - pharmacology</subject><subject>Neoplasms - drug therapy</subject><subject>Oximes</subject><subject>Oximes - chemical synthesis</subject><subject>Oximes - chemistry</subject><subject>Oximes - pharmacology</subject><subject>Scrophulariaceae - chemistry</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1rFEEQhhtRzCb6BzzIHD04Y9f0x0yDFwnRCIEcTMCLNP1RQ3qZmY7dvTHrr7eXjR49FVU87wv1EPIGaAcU5IdtZxc3dz0F0QF0VIlnZANc8pZxKp6TDVWStqPi30_Iac5bSoFTzl-Sk17KkY-CbsiPb_u13GEO-X1j1hKscQVTMHPdfOP2JZb4GFxTz-EhlIC5iVOz4q_GhmmOKaytNRl9c7f3yfyOawUOyRpaML8iLyYzZ3z9NM_I7eeLm_PL9ur6y9fzT1etY0KWlklgg-IjWOa5Eei8BYNSguB0ZNaCH4feCjXBIIYRLeIgmFGMKQvjpCg7I--Ovfcp_txhLnoJ2eE8mxXjLmsYJFVUsp5VtD-iLsWcE076PoXFpL0Gqg9a9VYftOqDVg2gq9YaevvUv7ML-n-Rvx4r8PEIYP3yIWDS2QVcHfqQ0BXtY_hf_x9FconW</recordid><startdate>20160115</startdate><enddate>20160115</enddate><creator>da S. 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Souza, Luciana G. ; Almeida, Macia C.S. ; Lemos, Telma L.G. ; Ribeiro, Paulo R.V. ; de Brito, Edy S. ; Silva, Vera L.M. ; Silva, Artur M.S. ; Braz-Filho, Raimundo ; Costa, José G.M. ; Rodrigues, Fábio F.G. ; Barreto, Francisco S. ; de Moraes, Manoel O.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-361379481b3d4a5ecdb1ae66154083bb1d872b59f17578ebee753a9339b18f903</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial</topic><topic>Antineoplastic Agents, Phytogenic - chemical synthesis</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Antitumoral</topic><topic>Bacteria - drug effects</topic><topic>Bacterial Infections - drug therapy</topic><topic>Biflorin</topic><topic>Cell Line, Tumor</topic><topic>Humans</topic><topic>Hydrazones</topic><topic>Hydrazones - chemical synthesis</topic><topic>Hydrazones - chemistry</topic><topic>Hydrazones - pharmacology</topic><topic>Microbial Sensitivity Tests</topic><topic>Naphthoquinones - chemical synthesis</topic><topic>Naphthoquinones - chemistry</topic><topic>Naphthoquinones - pharmacology</topic><topic>Neoplasms - drug therapy</topic><topic>Oximes</topic><topic>Oximes - chemical synthesis</topic><topic>Oximes - chemistry</topic><topic>Oximes - pharmacology</topic><topic>Scrophulariaceae - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>da S. 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Souza, Luciana G.</au><au>Almeida, Macia C.S.</au><au>Lemos, Telma L.G.</au><au>Ribeiro, Paulo R.V.</au><au>de Brito, Edy S.</au><au>Silva, Vera L.M.</au><au>Silva, Artur M.S.</au><au>Braz-Filho, Raimundo</au><au>Costa, José G.M.</au><au>Rodrigues, Fábio F.G.</au><au>Barreto, Francisco S.</au><au>de Moraes, Manoel O.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, antibacterial and cytotoxic activities of new biflorin-based hydrazones and oximes</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2016-01-15</date><risdate>2016</risdate><volume>26</volume><issue>2</issue><spage>435</spage><epage>439</epage><pages>435-439</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
Biflorin 1 is a biologically active quinone, isolated from Capraria biflora. Five new biflorin-based nitrogen derivatives were synthesized, of which two were mixtures of (E)- and (Z)- isomers: (Z)-2a, (Z)-2b, (Z)-3a, (Z)- and (E)-3b, (Z)- and (E)-3c. The antibacterial activity was investigated using the microdilution method for determining the minimum inhibitory concentration (MIC) against six bacterial strains. Tests have shown that these derivatives have potential against all bacterial strains. The cytotoxic activity was also evaluated against three strains of cancer cells, but none of the derivatives showed activity.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>26684850</pmid><doi>10.1016/j.bmcl.2015.11.095</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-4084-8076</orcidid></addata></record> |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibacterial Antineoplastic Agents, Phytogenic - chemical synthesis Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - pharmacology Antitumoral Bacteria - drug effects Bacterial Infections - drug therapy Biflorin Cell Line, Tumor Humans Hydrazones Hydrazones - chemical synthesis Hydrazones - chemistry Hydrazones - pharmacology Microbial Sensitivity Tests Naphthoquinones - chemical synthesis Naphthoquinones - chemistry Naphthoquinones - pharmacology Neoplasms - drug therapy Oximes Oximes - chemical synthesis Oximes - chemistry Oximes - pharmacology Scrophulariaceae - chemistry |
| title | Synthesis, antibacterial and cytotoxic activities of new biflorin-based hydrazones and oximes |
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