One-pot catalyst free synthesis of novel kojic acid tagged 2-aryl/alkyl substituted-4H-chromenes and evaluation of their antimicrobial and anti-biofilm activities
A number of 3-hydroxy-6-(hydroxymethyl)-2-(2-phenyl-4H-chromen-4-yl)-4H-pyran-4-ones (3) have been synthesized in a one pot catalyst free reaction of 2-hydroxy chalcone (1) with kojic acid (2) in toluene at reflux temperature and evaluated for antimicrobial and anti-biofilm activities. Compounds 3a,...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2015-05, Vol.25 (9), p.1915-1919 |
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| container_end_page | 1919 |
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| container_issue | 9 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 25 |
| creator | Bingi, Chiranjeevi Emmadi, Narender Reddy Chennapuram, Madhu Poornachandra, Y Kumar, C Ganesh Nanubolu, Jagadeesh Babu Atmakur, Krishnaiah |
| description | A number of 3-hydroxy-6-(hydroxymethyl)-2-(2-phenyl-4H-chromen-4-yl)-4H-pyran-4-ones (3) have been synthesized in a one pot catalyst free reaction of 2-hydroxy chalcone (1) with kojic acid (2) in toluene at reflux temperature and evaluated for antimicrobial and anti-biofilm activities. Compounds 3a, 3e, 3f, 3l showed potent antimicrobial activity against Staphylococcus aureus MLS-16 MTCC 2940, Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739, whereas 3b and 3k exhibited excellent activity against Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739, while 3g showed promising activity against Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739. On the other hand, compounds 3a, 3b and 3l showed very good anti-biofilm activity and 3g showed moderate activity against Bacillus subtilis MTCC 121. Whereas, compounds 3a and 3f showed moderate activity against Escherichia coli MTCC 739, while compounds 3a, 3b, 3k and 3l displayed similar activity against Staphylococcus aureus MLS-16 MTCC 2940. |
| doi_str_mv | 10.1016/j.bmcl.2015.03.034 |
| format | Article |
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Compounds 3a, 3e, 3f, 3l showed potent antimicrobial activity against Staphylococcus aureus MLS-16 MTCC 2940, Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739, whereas 3b and 3k exhibited excellent activity against Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739, while 3g showed promising activity against Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739. On the other hand, compounds 3a, 3b and 3l showed very good anti-biofilm activity and 3g showed moderate activity against Bacillus subtilis MTCC 121. Whereas, compounds 3a and 3f showed moderate activity against Escherichia coli MTCC 739, while compounds 3a, 3b, 3k and 3l displayed similar activity against Staphylococcus aureus MLS-16 MTCC 2940.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2015.03.034</identifier><identifier>PMID: 25838145</identifier><language>eng</language><publisher>England</publisher><subject>Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Bacillus subtilis - drug effects ; Benzopyrans - chemical synthesis ; Benzopyrans - chemistry ; Benzopyrans - pharmacology ; Biofilms - drug effects ; Dose-Response Relationship, Drug ; Escherichia coli - drug effects ; Microbial Sensitivity Tests ; Models, Molecular ; Molecular Structure ; Pyrones - chemistry ; Staphylococcus aureus - drug effects</subject><ispartof>Bioorganic & medicinal chemistry letters, 2015-05, Vol.25 (9), p.1915-1919</ispartof><rights>Copyright © 2015 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c373t-2f7c1f1803dfe3784d79443771ba861180d318f93d40f9328b95124d5094e59d3</citedby><cites>FETCH-LOGICAL-c373t-2f7c1f1803dfe3784d79443771ba861180d318f93d40f9328b95124d5094e59d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25838145$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bingi, Chiranjeevi</creatorcontrib><creatorcontrib>Emmadi, Narender Reddy</creatorcontrib><creatorcontrib>Chennapuram, Madhu</creatorcontrib><creatorcontrib>Poornachandra, Y</creatorcontrib><creatorcontrib>Kumar, C Ganesh</creatorcontrib><creatorcontrib>Nanubolu, Jagadeesh Babu</creatorcontrib><creatorcontrib>Atmakur, Krishnaiah</creatorcontrib><title>One-pot catalyst free synthesis of novel kojic acid tagged 2-aryl/alkyl substituted-4H-chromenes and evaluation of their antimicrobial and anti-biofilm activities</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A number of 3-hydroxy-6-(hydroxymethyl)-2-(2-phenyl-4H-chromen-4-yl)-4H-pyran-4-ones (3) have been synthesized in a one pot catalyst free reaction of 2-hydroxy chalcone (1) with kojic acid (2) in toluene at reflux temperature and evaluated for antimicrobial and anti-biofilm activities. Compounds 3a, 3e, 3f, 3l showed potent antimicrobial activity against Staphylococcus aureus MLS-16 MTCC 2940, Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739, whereas 3b and 3k exhibited excellent activity against Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739, while 3g showed promising activity against Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739. On the other hand, compounds 3a, 3b and 3l showed very good anti-biofilm activity and 3g showed moderate activity against Bacillus subtilis MTCC 121. Whereas, compounds 3a and 3f showed moderate activity against Escherichia coli MTCC 739, while compounds 3a, 3b, 3k and 3l displayed similar activity against Staphylococcus aureus MLS-16 MTCC 2940.</description><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Bacillus subtilis - drug effects</subject><subject>Benzopyrans - chemical synthesis</subject><subject>Benzopyrans - chemistry</subject><subject>Benzopyrans - pharmacology</subject><subject>Biofilms - drug effects</subject><subject>Dose-Response Relationship, Drug</subject><subject>Escherichia coli - drug effects</subject><subject>Microbial Sensitivity Tests</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Pyrones - chemistry</subject><subject>Staphylococcus aureus - drug effects</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9UcFq3DAQFaWl2aT9gR6Cjr1oI1myJR9LaJpAIJcWehOyNEq0ka2NJS_s7-RLIzdJYZiBN2_eDPMQ-sbollHWXey2w2jjtqGs3VJeQ3xAGyY6Qbig7Ue0oX1HierF3xN0mvOOUiaoEJ_RSdMqrphoN-j5bgKyTwVbU0w85oL9DIDzcSoPkEPGyeMpHSDix7QLFhsbHC7m_h4cboiZj_HCxMdjxHkZcgllKeCIuCb2YU4jTJCxmRyGg4mLKSFNq15VDnPFSxiDndMQTPzHWhEyhORDHOuiEg6hBMhf0CdvYoavb_UM_bn6-fvymtze_bq5_HFLLJe8kMZLyzxTlDsPXCrhZC8El5INRnWsNhxnyvfcCVpzo4a-ZY1wLe0FtL3jZ-j7q-5-Tk8L5KLHkC3EaCZIS9ask62Sksq-UptXaj0_5xm83s9hrN_QjOrVG73Tqzd69UZTXkPUofM3_WUYwf0feTeDvwD3_I4D</recordid><startdate>20150501</startdate><enddate>20150501</enddate><creator>Bingi, Chiranjeevi</creator><creator>Emmadi, Narender Reddy</creator><creator>Chennapuram, Madhu</creator><creator>Poornachandra, Y</creator><creator>Kumar, C Ganesh</creator><creator>Nanubolu, Jagadeesh Babu</creator><creator>Atmakur, Krishnaiah</creator><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>20150501</creationdate><title>One-pot catalyst free synthesis of novel kojic acid tagged 2-aryl/alkyl substituted-4H-chromenes and evaluation of their antimicrobial and anti-biofilm activities</title><author>Bingi, Chiranjeevi ; Emmadi, Narender Reddy ; Chennapuram, Madhu ; Poornachandra, Y ; Kumar, C Ganesh ; Nanubolu, Jagadeesh Babu ; Atmakur, Krishnaiah</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c373t-2f7c1f1803dfe3784d79443771ba861180d318f93d40f9328b95124d5094e59d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Bacillus subtilis - drug effects</topic><topic>Benzopyrans - chemical synthesis</topic><topic>Benzopyrans - chemistry</topic><topic>Benzopyrans - pharmacology</topic><topic>Biofilms - drug effects</topic><topic>Dose-Response Relationship, Drug</topic><topic>Escherichia coli - drug effects</topic><topic>Microbial Sensitivity Tests</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Pyrones - chemistry</topic><topic>Staphylococcus aureus - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bingi, Chiranjeevi</creatorcontrib><creatorcontrib>Emmadi, Narender Reddy</creatorcontrib><creatorcontrib>Chennapuram, Madhu</creatorcontrib><creatorcontrib>Poornachandra, Y</creatorcontrib><creatorcontrib>Kumar, C Ganesh</creatorcontrib><creatorcontrib>Nanubolu, Jagadeesh Babu</creatorcontrib><creatorcontrib>Atmakur, Krishnaiah</creatorcontrib><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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bingi, Chiranjeevi</au><au>Emmadi, Narender Reddy</au><au>Chennapuram, Madhu</au><au>Poornachandra, Y</au><au>Kumar, C Ganesh</au><au>Nanubolu, Jagadeesh Babu</au><au>Atmakur, Krishnaiah</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-pot catalyst free synthesis of novel kojic acid tagged 2-aryl/alkyl substituted-4H-chromenes and evaluation of their antimicrobial and anti-biofilm activities</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2015-05-01</date><risdate>2015</risdate><volume>25</volume><issue>9</issue><spage>1915</spage><epage>1919</epage><pages>1915-1919</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A number of 3-hydroxy-6-(hydroxymethyl)-2-(2-phenyl-4H-chromen-4-yl)-4H-pyran-4-ones (3) have been synthesized in a one pot catalyst free reaction of 2-hydroxy chalcone (1) with kojic acid (2) in toluene at reflux temperature and evaluated for antimicrobial and anti-biofilm activities. Compounds 3a, 3e, 3f, 3l showed potent antimicrobial activity against Staphylococcus aureus MLS-16 MTCC 2940, Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739, whereas 3b and 3k exhibited excellent activity against Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739, while 3g showed promising activity against Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739. On the other hand, compounds 3a, 3b and 3l showed very good anti-biofilm activity and 3g showed moderate activity against Bacillus subtilis MTCC 121. Whereas, compounds 3a and 3f showed moderate activity against Escherichia coli MTCC 739, while compounds 3a, 3b, 3k and 3l displayed similar activity against Staphylococcus aureus MLS-16 MTCC 2940.</abstract><cop>England</cop><pmid>25838145</pmid><doi>10.1016/j.bmcl.2015.03.034</doi><tpages>5</tpages></addata></record> |
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| subjects | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Bacillus subtilis - drug effects Benzopyrans - chemical synthesis Benzopyrans - chemistry Benzopyrans - pharmacology Biofilms - drug effects Dose-Response Relationship, Drug Escherichia coli - drug effects Microbial Sensitivity Tests Models, Molecular Molecular Structure Pyrones - chemistry Staphylococcus aureus - drug effects |
| title | One-pot catalyst free synthesis of novel kojic acid tagged 2-aryl/alkyl substituted-4H-chromenes and evaluation of their antimicrobial and anti-biofilm activities |
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