Synthesis and antibacterial activity of fluorinated carbazoles
In our previous studies, fluorine-substituted carbazoles were synthesized, and these compounds showed promising potential against Gram-positive bacterial stains, including Methicillin-resistant Staphylococcus aureus . However, only three compounds with two F substituents on the 2,4-positions of carb...
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| Veröffentlicht in: | Chemical papers 2019-10, Vol.73 (10), p.2477-2484 |
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| creator | Zhou, Sheng-liang Tang, Hui-ling Yao, Miao Cao, Shi-nian Zhuang, Li-yuan Cao, Chang-sheng Shi, Yan-hui |
| description | In our previous studies, fluorine-substituted carbazoles were synthesized, and these compounds showed promising potential against Gram-positive bacterial stains, including Methicillin-resistant
Staphylococcus aureus
. However, only three compounds with two F substituents on the 2,4-positions of carbazole showed antibacterial potency against both Gram-positive and Gram-negative bacterial strains. A series of new compounds with two F substituents on the 2,4-positions of carbazole, besides three known ones, were synthesized. The structures were confirmed by infrared spectroscopy,
1
H &
13
C nuclear magnetic resonance spectroscopy, and high-resolution mass spectrometry. Eight compounds showed antibacterial activity. 2,4,6-Trifluoro-9
H
-carbazole (
2
), with simple structure, showed potential antibacterial activity against the multidrug resistant NDM-1-producing strains which are not inhibited by commonly used antibiotics. Its water-soluble salt was synthesized but showed less activity. |
| doi_str_mv | 10.1007/s11696-019-00798-7 |
| format | Article |
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Staphylococcus aureus
. However, only three compounds with two F substituents on the 2,4-positions of carbazole showed antibacterial potency against both Gram-positive and Gram-negative bacterial strains. A series of new compounds with two F substituents on the 2,4-positions of carbazole, besides three known ones, were synthesized. The structures were confirmed by infrared spectroscopy,
1
H &
13
C nuclear magnetic resonance spectroscopy, and high-resolution mass spectrometry. Eight compounds showed antibacterial activity. 2,4,6-Trifluoro-9
H
-carbazole (
2
), with simple structure, showed potential antibacterial activity against the multidrug resistant NDM-1-producing strains which are not inhibited by commonly used antibiotics. Its water-soluble salt was synthesized but showed less activity.</description><identifier>ISSN: 2585-7290</identifier><identifier>ISSN: 0366-6352</identifier><identifier>EISSN: 1336-9075</identifier><identifier>DOI: 10.1007/s11696-019-00798-7</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Antibacterial materials ; Antibiotics ; Biochemistry ; Biotechnology ; Carbazoles ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Fluorination ; Fluorine ; Industrial Chemistry/Chemical Engineering ; Mass spectrometry ; Materials Science ; Medicinal Chemistry ; NMR ; Nuclear magnetic resonance ; Original Paper ; Staphylococcus infections ; Synthesis</subject><ispartof>Chemical papers, 2019-10, Vol.73 (10), p.2477-2484</ispartof><rights>Institute of Chemistry, Slovak Academy of Sciences 2019</rights><rights>Copyright Springer Nature B.V. 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-17cea031857c83249aab0c90a1e3b337499753b3717f9446d734a46e7811b2033</citedby><cites>FETCH-LOGICAL-c319t-17cea031857c83249aab0c90a1e3b337499753b3717f9446d734a46e7811b2033</cites><orcidid>0000-0003-2124-7988</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11696-019-00798-7$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11696-019-00798-7$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Zhou, Sheng-liang</creatorcontrib><creatorcontrib>Tang, Hui-ling</creatorcontrib><creatorcontrib>Yao, Miao</creatorcontrib><creatorcontrib>Cao, Shi-nian</creatorcontrib><creatorcontrib>Zhuang, Li-yuan</creatorcontrib><creatorcontrib>Cao, Chang-sheng</creatorcontrib><creatorcontrib>Shi, Yan-hui</creatorcontrib><title>Synthesis and antibacterial activity of fluorinated carbazoles</title><title>Chemical papers</title><addtitle>Chem. Pap</addtitle><description>In our previous studies, fluorine-substituted carbazoles were synthesized, and these compounds showed promising potential against Gram-positive bacterial stains, including Methicillin-resistant
Staphylococcus aureus
. However, only three compounds with two F substituents on the 2,4-positions of carbazole showed antibacterial potency against both Gram-positive and Gram-negative bacterial strains. A series of new compounds with two F substituents on the 2,4-positions of carbazole, besides three known ones, were synthesized. The structures were confirmed by infrared spectroscopy,
1
H &
13
C nuclear magnetic resonance spectroscopy, and high-resolution mass spectrometry. Eight compounds showed antibacterial activity. 2,4,6-Trifluoro-9
H
-carbazole (
2
), with simple structure, showed potential antibacterial activity against the multidrug resistant NDM-1-producing strains which are not inhibited by commonly used antibiotics. Its water-soluble salt was synthesized but showed less activity.</description><subject>Antibacterial materials</subject><subject>Antibiotics</subject><subject>Biochemistry</subject><subject>Biotechnology</subject><subject>Carbazoles</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Fluorination</subject><subject>Fluorine</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Mass spectrometry</subject><subject>Materials Science</subject><subject>Medicinal Chemistry</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Original Paper</subject><subject>Staphylococcus infections</subject><subject>Synthesis</subject><issn>2585-7290</issn><issn>0366-6352</issn><issn>1336-9075</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kE9LAzEQxYMoWGq_gKcFz9FM_uxsLoIUtULBg3oO2TSrkXW3JqlQP73RFbx5GOYNvPcGfoScAjsHxvAiAdS6pgw0LaduKB6QGQhRU81QHZIZV42iyDU7JouUQsukRMGbGmfk8mE_5BefQqrssCmTQ2td9jHYvioifIS8r8au6vrdGMNgs99UzsbWfo69TyfkqLN98ovfPSdPN9ePyxVd39_eLa_W1AnQmQI6b5mARqFrBJfa2pY5zSx40QqBUmtURSFgp6WsNyiklbXHBqDlTIg5OZt6t3F83_mUzeu4i0N5aThXXAAqzYuLTy4Xx5Si78w2hjcb9waY-UZlJlSmoDI_qAyWkJhCqZiHZx__qv9JfQEOsGq0</recordid><startdate>20191001</startdate><enddate>20191001</enddate><creator>Zhou, Sheng-liang</creator><creator>Tang, Hui-ling</creator><creator>Yao, Miao</creator><creator>Cao, Shi-nian</creator><creator>Zhuang, Li-yuan</creator><creator>Cao, Chang-sheng</creator><creator>Shi, Yan-hui</creator><general>Springer International Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0003-2124-7988</orcidid></search><sort><creationdate>20191001</creationdate><title>Synthesis and antibacterial activity of fluorinated carbazoles</title><author>Zhou, Sheng-liang ; Tang, Hui-ling ; Yao, Miao ; Cao, Shi-nian ; Zhuang, Li-yuan ; Cao, Chang-sheng ; Shi, Yan-hui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-17cea031857c83249aab0c90a1e3b337499753b3717f9446d734a46e7811b2033</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Antibacterial materials</topic><topic>Antibiotics</topic><topic>Biochemistry</topic><topic>Biotechnology</topic><topic>Carbazoles</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Fluorination</topic><topic>Fluorine</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Mass spectrometry</topic><topic>Materials Science</topic><topic>Medicinal Chemistry</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Original Paper</topic><topic>Staphylococcus infections</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhou, Sheng-liang</creatorcontrib><creatorcontrib>Tang, Hui-ling</creatorcontrib><creatorcontrib>Yao, Miao</creatorcontrib><creatorcontrib>Cao, Shi-nian</creatorcontrib><creatorcontrib>Zhuang, Li-yuan</creatorcontrib><creatorcontrib>Cao, Chang-sheng</creatorcontrib><creatorcontrib>Shi, Yan-hui</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chemical papers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhou, Sheng-liang</au><au>Tang, Hui-ling</au><au>Yao, Miao</au><au>Cao, Shi-nian</au><au>Zhuang, Li-yuan</au><au>Cao, Chang-sheng</au><au>Shi, Yan-hui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and antibacterial activity of fluorinated carbazoles</atitle><jtitle>Chemical papers</jtitle><stitle>Chem. Pap</stitle><date>2019-10-01</date><risdate>2019</risdate><volume>73</volume><issue>10</issue><spage>2477</spage><epage>2484</epage><pages>2477-2484</pages><issn>2585-7290</issn><issn>0366-6352</issn><eissn>1336-9075</eissn><abstract>In our previous studies, fluorine-substituted carbazoles were synthesized, and these compounds showed promising potential against Gram-positive bacterial stains, including Methicillin-resistant
Staphylococcus aureus
. However, only three compounds with two F substituents on the 2,4-positions of carbazole showed antibacterial potency against both Gram-positive and Gram-negative bacterial strains. A series of new compounds with two F substituents on the 2,4-positions of carbazole, besides three known ones, were synthesized. The structures were confirmed by infrared spectroscopy,
1
H &
13
C nuclear magnetic resonance spectroscopy, and high-resolution mass spectrometry. Eight compounds showed antibacterial activity. 2,4,6-Trifluoro-9
H
-carbazole (
2
), with simple structure, showed potential antibacterial activity against the multidrug resistant NDM-1-producing strains which are not inhibited by commonly used antibiotics. Its water-soluble salt was synthesized but showed less activity.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><doi>10.1007/s11696-019-00798-7</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-2124-7988</orcidid></addata></record> |
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| source | Springer Nature - Complete Springer Journals |
| subjects | Antibacterial materials Antibiotics Biochemistry Biotechnology Carbazoles Chemistry Chemistry and Materials Science Chemistry/Food Science Fluorination Fluorine Industrial Chemistry/Chemical Engineering Mass spectrometry Materials Science Medicinal Chemistry NMR Nuclear magnetic resonance Original Paper Staphylococcus infections Synthesis |
| title | Synthesis and antibacterial activity of fluorinated carbazoles |
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