Synthesis of novel ciprofloxacin analogues and evaluation of their anti-proliferative effect on human cancer cell lines
A series of twenty two novel 1-cyclopropyl-6-fluoro-4-oxo-7-(4-substituted piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid analogues have been synthesized, characterized (1H NMR, 13C NMR and LCMS) and evaluated for their inhibitory activity on the proliferation of human caucasian acute lympho...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2013-12, Vol.23 (23), p.6292-6295 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Suresh, Narva Nagesh, Hunsur Nagendra Chandra Sekhar, Kondapalli Venkata Gowri Kumar, Anil Shirazi, Amir N. Parang, Keykavous |
| description | A series of twenty two novel 1-cyclopropyl-6-fluoro-4-oxo-7-(4-substituted piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid analogues have been synthesized, characterized (1H NMR, 13C NMR and LCMS) and evaluated for their inhibitory activity on the proliferation of human caucasian acute lymphoblastic leukemia cells (CCRF-CEM), breast adenocarcinoma cells (MDA-MB-468) and human colon carcinoma cells (HCT-116). Among all the synthesized ciprofloxacin analogues 3t at 50μM showed comparable potency to doxorubicin (10μM) in all three cell lines and 3j inhibited proliferation of MDA-MB-468 up to 35% selectively over other two cell lines. |
| doi_str_mv | 10.1016/j.bmcl.2013.09.077 |
| format | Article |
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Among all the synthesized ciprofloxacin analogues 3t at 50μM showed comparable potency to doxorubicin (10μM) in all three cell lines and 3j inhibited proliferation of MDA-MB-468 up to 35% selectively over other two cell lines.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2013.09.077</identifier><identifier>PMID: 24138941</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>adenocarcinoma ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Anti-cancer ; Anti-proliferative ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Cell Line, Tumor ; chemistry ; Ciprofloxacin ; Ciprofloxacin - analogs & derivatives ; Ciprofloxacin - chemical synthesis ; Ciprofloxacin - chemistry ; Ciprofloxacin - pharmacology ; colorectal neoplasms ; doxorubicin ; Drug Screening Assays, Antitumor ; Fluoroquinolones ; Fluoroquinolones - chemical synthesis ; Fluoroquinolones - chemistry ; Fluoroquinolones - pharmacology ; Humans ; lymphocytic leukemia ; Molecular Structure ; nuclear magnetic resonance spectroscopy ; Structure-Activity Relationship ; Substituted piperazines</subject><ispartof>Bioorganic & medicinal chemistry letters, 2013-12, Vol.23 (23), p.6292-6295</ispartof><rights>2013 Elsevier Ltd</rights><rights>Copyright © 2013 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c457t-cd66904b85fa1bc62101b943714a92c1e40741eb86d4978f346d6a4357e3e4df3</citedby><cites>FETCH-LOGICAL-c457t-cd66904b85fa1bc62101b943714a92c1e40741eb86d4978f346d6a4357e3e4df3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2013.09.077$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24138941$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Suresh, Narva</creatorcontrib><creatorcontrib>Nagesh, Hunsur Nagendra</creatorcontrib><creatorcontrib>Chandra Sekhar, Kondapalli Venkata Gowri</creatorcontrib><creatorcontrib>Kumar, Anil</creatorcontrib><creatorcontrib>Shirazi, Amir N.</creatorcontrib><creatorcontrib>Parang, Keykavous</creatorcontrib><title>Synthesis of novel ciprofloxacin analogues and evaluation of their anti-proliferative effect on human cancer cell lines</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A series of twenty two novel 1-cyclopropyl-6-fluoro-4-oxo-7-(4-substituted piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid analogues have been synthesized, characterized (1H NMR, 13C NMR and LCMS) and evaluated for their inhibitory activity on the proliferation of human caucasian acute lymphoblastic leukemia cells (CCRF-CEM), breast adenocarcinoma cells (MDA-MB-468) and human colon carcinoma cells (HCT-116). Among all the synthesized ciprofloxacin analogues 3t at 50μM showed comparable potency to doxorubicin (10μM) in all three cell lines and 3j inhibited proliferation of MDA-MB-468 up to 35% selectively over other two cell lines.</description><subject>adenocarcinoma</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Anti-cancer</subject><subject>Anti-proliferative</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>chemistry</subject><subject>Ciprofloxacin</subject><subject>Ciprofloxacin - analogs & derivatives</subject><subject>Ciprofloxacin - chemical synthesis</subject><subject>Ciprofloxacin - chemistry</subject><subject>Ciprofloxacin - pharmacology</subject><subject>colorectal neoplasms</subject><subject>doxorubicin</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Fluoroquinolones</subject><subject>Fluoroquinolones - chemical synthesis</subject><subject>Fluoroquinolones - chemistry</subject><subject>Fluoroquinolones - pharmacology</subject><subject>Humans</subject><subject>lymphocytic leukemia</subject><subject>Molecular Structure</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Structure-Activity Relationship</subject><subject>Substituted piperazines</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU9v1DAQxS0EokvhC3AAH7kk2PHESSQuqOKfVIlDqcTNcpxx65U3Lnay0G_PRFs4wsmW_XtPb-Yx9lKKWgqp3-7r8eBi3QipajHUousesZ0EDZUC0T5mOzFoUfUDfD9jz0rZCyFBADxlZw1IRe9yx35e3c_LLZZQePJ8TkeM3IW7nHxMv6wLM7ezjelmxUK3iePRxtUuIc0bT8qQ6X0JFUli8Jjp74gcvUe3cKJu14OdubOzw8wdxshjmLE8Z0-8jQVfPJzn7Prjh28Xn6vLr5--XLy_rBy03VK5SetBwNi33srR6YYGHwdQnQQ7NE4iiA4kjr2eYOh6r0BP2oJqO1QIk1fn7M3Jl_L9oCEWcwhli2FnTGsxshWia7u-Vf9HAfpGDA1oQpsT6nIqJaM3dzkcbL43UpitG7M3Wzdm68aIwVA3JHr14L-OB5z-Sv6UQcDrE-BtMvYmh2Kur8iBIkrV6GazeHcikFZ2DJhNcQFptVPItG8zpfCvBL8BxfmqNA</recordid><startdate>20131201</startdate><enddate>20131201</enddate><creator>Suresh, Narva</creator><creator>Nagesh, Hunsur Nagendra</creator><creator>Chandra Sekhar, Kondapalli Venkata Gowri</creator><creator>Kumar, Anil</creator><creator>Shirazi, Amir N.</creator><creator>Parang, Keykavous</creator><general>Elsevier Ltd</general><scope>FBQ</scope><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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20131201</creationdate><title>Synthesis of novel ciprofloxacin analogues and evaluation of their anti-proliferative effect on human cancer cell lines</title><author>Suresh, Narva ; 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| subjects | adenocarcinoma Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Anti-cancer Anti-proliferative Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Cell Line, Tumor chemistry Ciprofloxacin Ciprofloxacin - analogs & derivatives Ciprofloxacin - chemical synthesis Ciprofloxacin - chemistry Ciprofloxacin - pharmacology colorectal neoplasms doxorubicin Drug Screening Assays, Antitumor Fluoroquinolones Fluoroquinolones - chemical synthesis Fluoroquinolones - chemistry Fluoroquinolones - pharmacology Humans lymphocytic leukemia Molecular Structure nuclear magnetic resonance spectroscopy Structure-Activity Relationship Substituted piperazines |
| title | Synthesis of novel ciprofloxacin analogues and evaluation of their anti-proliferative effect on human cancer cell lines |
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