New Hydroxamic Acid Derivatives of Fluoroquinolones: Synthesis and Evaluation of Antibacterial and Anticancer Properties
A series of new hydroxamic acid derivatives (6a–f) at C-3 position of fluoroquinolones were designed and synthesized through multistep synthesis. The design concept involved replacement of the 3-carboxylic acid in fluoquinolones with hydroxamic acid as an acid mimicking group. The synthetic work emp...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2014/02/01, Vol.62(2), pp.168-175 |
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| creator | Rajulu, Gavara Govinda Naik, Halehatty Seephya Bhojya Viswanadhan, Abhilash Thiruvengadam, Jayaraman Rajesh, Kondodiyil Ganesh, Sambasivam Jagadheshan, Hiriyan Kesavan, Poonimangadu Koppolu |
| description | A series of new hydroxamic acid derivatives (6a–f) at C-3 position of fluoroquinolones were designed and synthesized through multistep synthesis. The design concept involved replacement of the 3-carboxylic acid in fluoquinolones with hydroxamic acid as an acid mimicking group. The synthetic work employed in this work provides a good example for the synthesis of pure hydroxamic acid based fluoroquinolones. The synthesized compounds were characterized by 1H-NMR, electrospray ionization (ESI)-MS and IR. The new compounds were tested for their in vitro antimicrobial and anti-proliferative activity. Out of the six derivatives, compound 6e exhibited moderate antibacterial activity by inhibiting the growth of Escherichia coli and Klebsiella pneumoniae (MIC: 4.00–8.00 µg/mL). Compounds 6b and 6f displayed good growth inhibition against A549 Lung adenocarcinoma and HCT-116 Colon carcinoma cell lines. |
| doi_str_mv | 10.1248/cpb.c13-00797 |
| format | Article |
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The design concept involved replacement of the 3-carboxylic acid in fluoquinolones with hydroxamic acid as an acid mimicking group. The synthetic work employed in this work provides a good example for the synthesis of pure hydroxamic acid based fluoroquinolones. The synthesized compounds were characterized by 1H-NMR, electrospray ionization (ESI)-MS and IR. The new compounds were tested for their in vitro antimicrobial and anti-proliferative activity. Out of the six derivatives, compound 6e exhibited moderate antibacterial activity by inhibiting the growth of Escherichia coli and Klebsiella pneumoniae (MIC: 4.00–8.00 µg/mL). Compounds 6b and 6f displayed good growth inhibition against A549 Lung adenocarcinoma and HCT-116 Colon carcinoma cell lines.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.c13-00797</identifier><identifier>PMID: 24270473</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>[1,2,3]triazolyl derivative ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; antibacterial activity ; anticancer activity ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Escherichia coli - drug effects ; Escherichia coli - growth & development ; Escherichia coli Infections - drug therapy ; fluoroquinolone ; Fluoroquinolones - chemical synthesis ; Fluoroquinolones - chemistry ; Fluoroquinolones - pharmacology ; Humans ; hydroxamic acid ; Hydroxamic Acids - chemical synthesis ; Hydroxamic Acids - chemistry ; Hydroxamic Acids - pharmacology ; Klebsiella Infections - drug therapy ; Klebsiella pneumoniae - drug effects ; Klebsiella pneumoniae - growth & development ; Magnetic Resonance Spectroscopy ; Microbial Sensitivity Tests ; Neoplasms - drug therapy ; Structure-Activity Relationship</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2014/02/01, Vol.62(2), pp.168-175</ispartof><rights>2014 The Pharmaceutical Society of Japan</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c674t-bf2f6038e7ea9266af0985b43bfc7563f6f113f93cfe92fe042ca5767ac1eebd3</citedby><cites>FETCH-LOGICAL-c674t-bf2f6038e7ea9266af0985b43bfc7563f6f113f93cfe92fe042ca5767ac1eebd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1876,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24270473$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rajulu, Gavara Govinda</creatorcontrib><creatorcontrib>Naik, Halehatty Seephya Bhojya</creatorcontrib><creatorcontrib>Viswanadhan, Abhilash</creatorcontrib><creatorcontrib>Thiruvengadam, Jayaraman</creatorcontrib><creatorcontrib>Rajesh, Kondodiyil</creatorcontrib><creatorcontrib>Ganesh, Sambasivam</creatorcontrib><creatorcontrib>Jagadheshan, Hiriyan</creatorcontrib><creatorcontrib>Kesavan, Poonimangadu Koppolu</creatorcontrib><creatorcontrib>School of Chemical Sciences</creatorcontrib><creatorcontrib>aAnthem Biosciences Pvt.Ltd</creatorcontrib><creatorcontrib>Kuvempu University</creatorcontrib><creatorcontrib>bDepartment of PG Studies and Research in Industrial Chemistry</creatorcontrib><title>New Hydroxamic Acid Derivatives of Fluoroquinolones: Synthesis and Evaluation of Antibacterial and Anticancer Properties</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A series of new hydroxamic acid derivatives (6a–f) at C-3 position of fluoroquinolones were designed and synthesized through multistep synthesis. The design concept involved replacement of the 3-carboxylic acid in fluoquinolones with hydroxamic acid as an acid mimicking group. The synthetic work employed in this work provides a good example for the synthesis of pure hydroxamic acid based fluoroquinolones. The synthesized compounds were characterized by 1H-NMR, electrospray ionization (ESI)-MS and IR. The new compounds were tested for their in vitro antimicrobial and anti-proliferative activity. Out of the six derivatives, compound 6e exhibited moderate antibacterial activity by inhibiting the growth of Escherichia coli and Klebsiella pneumoniae (MIC: 4.00–8.00 µg/mL). Compounds 6b and 6f displayed good growth inhibition against A549 Lung adenocarcinoma and HCT-116 Colon carcinoma cell lines.</description><subject>[1,2,3]triazolyl derivative</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>antibacterial activity</subject><subject>anticancer activity</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Escherichia coli - drug effects</subject><subject>Escherichia coli - growth & development</subject><subject>Escherichia coli Infections - drug therapy</subject><subject>fluoroquinolone</subject><subject>Fluoroquinolones - chemical synthesis</subject><subject>Fluoroquinolones - chemistry</subject><subject>Fluoroquinolones - pharmacology</subject><subject>Humans</subject><subject>hydroxamic acid</subject><subject>Hydroxamic Acids - chemical synthesis</subject><subject>Hydroxamic Acids - chemistry</subject><subject>Hydroxamic Acids - pharmacology</subject><subject>Klebsiella Infections - drug therapy</subject><subject>Klebsiella pneumoniae - drug effects</subject><subject>Klebsiella pneumoniae - growth & development</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Microbial Sensitivity Tests</subject><subject>Neoplasms - drug therapy</subject><subject>Structure-Activity Relationship</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkU1v1DAQhi1ERZfCkSvKkUtafyR2zG219Euq2krA2XKcMetVYi92snT_Pc5uWS4eyfPo9cxjhD4RfElo1VyZbXtpCCsxFlK8QQvCKlHWlLK3aIExliVlnJ2j9yltMKY1FuwdOqcVFbgSbIFeHuFPcbfvYnjRgzPF0riu-AbR7fTodpCKYIubfgox_J6cD33wkL4W3_d-XENyqdC-K653up8yHvxML_3oWm3GnKH7Q3--MdobiMVzDFuIo4P0AZ1Z3Sf4-Fov0M-b6x-ru_Lh6fZ-tXwoDRfVWLaWWo5ZAwK0pJxri2VTtxVrrRE1Z5ZbQpiVzFiQ1AKuqNG14EIbAtB27AJ9OeZu5xUgjWpwyUDfaw9hSopUUpLsSNYZLY-oiSGlCFZtoxt03CuC1SxbZdkqy1YH2Zn__Bo9tQN0J_qf3QzcHoHczQayvN55UJswRZ93ViYJs4bBKYpJlUM5xTSXWmHCm3yI_I9EimZOWh2TNmnUv-D0lM4uTQ-HwThVdD5OA_7vrnVU4Nlfz-irsA</recordid><startdate>20140201</startdate><enddate>20140201</enddate><creator>Rajulu, Gavara Govinda</creator><creator>Naik, Halehatty Seephya Bhojya</creator><creator>Viswanadhan, Abhilash</creator><creator>Thiruvengadam, Jayaraman</creator><creator>Rajesh, Kondodiyil</creator><creator>Ganesh, Sambasivam</creator><creator>Jagadheshan, Hiriyan</creator><creator>Kesavan, Poonimangadu Koppolu</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><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>20140201</creationdate><title>New Hydroxamic Acid Derivatives of Fluoroquinolones: Synthesis and Evaluation of Antibacterial and Anticancer Properties</title><author>Rajulu, Gavara Govinda ; Naik, Halehatty Seephya Bhojya ; Viswanadhan, Abhilash ; Thiruvengadam, Jayaraman ; Rajesh, Kondodiyil ; Ganesh, Sambasivam ; Jagadheshan, Hiriyan ; Kesavan, Poonimangadu Koppolu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c674t-bf2f6038e7ea9266af0985b43bfc7563f6f113f93cfe92fe042ca5767ac1eebd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>[1,2,3]triazolyl derivative</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>antibacterial activity</topic><topic>anticancer activity</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Escherichia coli - drug effects</topic><topic>Escherichia coli - growth & development</topic><topic>Escherichia coli Infections - drug therapy</topic><topic>fluoroquinolone</topic><topic>Fluoroquinolones - chemical synthesis</topic><topic>Fluoroquinolones - chemistry</topic><topic>Fluoroquinolones - pharmacology</topic><topic>Humans</topic><topic>hydroxamic acid</topic><topic>Hydroxamic Acids - chemical synthesis</topic><topic>Hydroxamic Acids - chemistry</topic><topic>Hydroxamic Acids - pharmacology</topic><topic>Klebsiella Infections - drug therapy</topic><topic>Klebsiella pneumoniae - drug effects</topic><topic>Klebsiella pneumoniae - growth & development</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Microbial Sensitivity Tests</topic><topic>Neoplasms - drug therapy</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rajulu, Gavara Govinda</creatorcontrib><creatorcontrib>Naik, Halehatty Seephya Bhojya</creatorcontrib><creatorcontrib>Viswanadhan, Abhilash</creatorcontrib><creatorcontrib>Thiruvengadam, Jayaraman</creatorcontrib><creatorcontrib>Rajesh, Kondodiyil</creatorcontrib><creatorcontrib>Ganesh, Sambasivam</creatorcontrib><creatorcontrib>Jagadheshan, Hiriyan</creatorcontrib><creatorcontrib>Kesavan, Poonimangadu Koppolu</creatorcontrib><creatorcontrib>School of Chemical Sciences</creatorcontrib><creatorcontrib>aAnthem Biosciences Pvt.Ltd</creatorcontrib><creatorcontrib>Kuvempu University</creatorcontrib><creatorcontrib>bDepartment of PG Studies and Research in Industrial Chemistry</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>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rajulu, Gavara Govinda</au><au>Naik, Halehatty Seephya Bhojya</au><au>Viswanadhan, Abhilash</au><au>Thiruvengadam, Jayaraman</au><au>Rajesh, Kondodiyil</au><au>Ganesh, Sambasivam</au><au>Jagadheshan, Hiriyan</au><au>Kesavan, Poonimangadu Koppolu</au><aucorp>School of Chemical Sciences</aucorp><aucorp>aAnthem Biosciences Pvt.Ltd</aucorp><aucorp>Kuvempu University</aucorp><aucorp>bDepartment of PG Studies and Research in Industrial Chemistry</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New Hydroxamic Acid Derivatives of Fluoroquinolones: Synthesis and Evaluation of Antibacterial and Anticancer Properties</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2014-02-01</date><risdate>2014</risdate><volume>62</volume><issue>2</issue><spage>168</spage><epage>175</epage><pages>168-175</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>A series of new hydroxamic acid derivatives (6a–f) at C-3 position of fluoroquinolones were designed and synthesized through multistep synthesis. The design concept involved replacement of the 3-carboxylic acid in fluoquinolones with hydroxamic acid as an acid mimicking group. The synthetic work employed in this work provides a good example for the synthesis of pure hydroxamic acid based fluoroquinolones. The synthesized compounds were characterized by 1H-NMR, electrospray ionization (ESI)-MS and IR. The new compounds were tested for their in vitro antimicrobial and anti-proliferative activity. Out of the six derivatives, compound 6e exhibited moderate antibacterial activity by inhibiting the growth of Escherichia coli and Klebsiella pneumoniae (MIC: 4.00–8.00 µg/mL). Compounds 6b and 6f displayed good growth inhibition against A549 Lung adenocarcinoma and HCT-116 Colon carcinoma cell lines.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>24270473</pmid><doi>10.1248/cpb.c13-00797</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | [1,2,3]triazolyl derivative Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology antibacterial activity anticancer activity Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Cell Line, Tumor Cell Proliferation - drug effects Escherichia coli - drug effects Escherichia coli - growth & development Escherichia coli Infections - drug therapy fluoroquinolone Fluoroquinolones - chemical synthesis Fluoroquinolones - chemistry Fluoroquinolones - pharmacology Humans hydroxamic acid Hydroxamic Acids - chemical synthesis Hydroxamic Acids - chemistry Hydroxamic Acids - pharmacology Klebsiella Infections - drug therapy Klebsiella pneumoniae - drug effects Klebsiella pneumoniae - growth & development Magnetic Resonance Spectroscopy Microbial Sensitivity Tests Neoplasms - drug therapy Structure-Activity Relationship |
| title | New Hydroxamic Acid Derivatives of Fluoroquinolones: Synthesis and Evaluation of Antibacterial and Anticancer Properties |
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