Design, synthesis and docking studies of new quinoline-3-carbohydrazide derivatives as antitubercular agents
Three new series of 4-hydroxy-8-trifluoromethyl-quinoline derivatives were synthesized through multi step reactions. All the newly synthesized compounds were characterized by spectral and elemental analyses. The structure of 5j was evidenced by X-ray crystallographic study. The newly synthesized tit...
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| Veröffentlicht in: | European journal of medicinal chemistry 2011-11, Vol.46 (11), p.5283-5292 |
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| container_title | European journal of medicinal chemistry |
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| creator | Thomas, K.D. Adhikari, Airody Vasudeva Telkar, Sandeep Chowdhury, Imran H. Mahmood, Riaz Pal, Nishith K. Row, Guru Sumesh, E. |
| description | Three new series of 4-hydroxy-8-trifluoromethyl-quinoline derivatives were synthesized through multi step reactions. All the newly synthesized compounds were characterized by spectral and elemental analyses. The structure of 5j was evidenced by X-ray crystallographic study. The newly synthesized title compounds were evaluated for their antimicrobial activities including antimycobacterial activity. Amongst the tested compounds, 5b, 5e, 5h, 5j, 6c and 7c displayed promising antimicrobial activity. The mode of action of these active compounds was carried out by docking of receptor enoyl-ACP reductase with newly synthesized candidate ligands, 5b, 5e, 5h, 5j and 6c.
Three new series of 4-hydroxy-8-trifluoromethyl-quinoline derivatives were synthesized and the most effective compounds have a MIC value of 0.625μg/mL against Mycobacterium tuberculosis H37Rv. [Display omitted]
▸New series of quinoline carbohydrazone derivatives were synthesized. ▸X-ray crystallographic study of the title compound 5j was carried out. ▸In vitro antibacterial and antimycobacterial screening were carried out. ▸Compounds 5b, 5e, 5h, 5j and 6c showed substantial antitubercular activity. ▸Docking studies were carried out. |
| doi_str_mv | 10.1016/j.ejmech.2011.07.033 |
| format | Article |
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Three new series of 4-hydroxy-8-trifluoromethyl-quinoline derivatives were synthesized and the most effective compounds have a MIC value of 0.625μg/mL against Mycobacterium tuberculosis H37Rv. [Display omitted]
▸New series of quinoline carbohydrazone derivatives were synthesized. ▸X-ray crystallographic study of the title compound 5j was carried out. ▸In vitro antibacterial and antimycobacterial screening were carried out. ▸Compounds 5b, 5e, 5h, 5j and 6c showed substantial antitubercular activity. ▸Docking studies were carried out.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2011.07.033</identifier><identifier>PMID: 21907466</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Kidlington: Elsevier Masson SAS</publisher><subject>Antibacterial ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antimycobacterial ; Antitubercular Agents - chemical synthesis ; Antitubercular Agents - chemistry ; Antitubercular Agents - pharmacology ; Bacteria - drug effects ; Biological and medical sciences ; Docking study ; Drug Design ; Hydrazines - chemical synthesis ; Hydrazines - chemistry ; Hydrazines - pharmacology ; Medical sciences ; Microbial Sensitivity Tests ; Models, Molecular ; Molecular Conformation ; Pharmacology. Drug treatments ; Quinoline ; Quinolines - chemistry ; X-ray crystallography</subject><ispartof>European journal of medicinal chemistry, 2011-11, Vol.46 (11), p.5283-5292</ispartof><rights>2011 Elsevier Masson SAS</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c457t-7f30b84b87533f7a6e1a16b87090f564725322dc2538165e384122b0114a9b003</citedby><cites>FETCH-LOGICAL-c457t-7f30b84b87533f7a6e1a16b87090f564725322dc2538165e384122b0114a9b003</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2011.07.033$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24730020$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21907466$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Thomas, K.D.</creatorcontrib><creatorcontrib>Adhikari, Airody Vasudeva</creatorcontrib><creatorcontrib>Telkar, Sandeep</creatorcontrib><creatorcontrib>Chowdhury, Imran H.</creatorcontrib><creatorcontrib>Mahmood, Riaz</creatorcontrib><creatorcontrib>Pal, Nishith K.</creatorcontrib><creatorcontrib>Row, Guru</creatorcontrib><creatorcontrib>Sumesh, E.</creatorcontrib><title>Design, synthesis and docking studies of new quinoline-3-carbohydrazide derivatives as antitubercular agents</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Three new series of 4-hydroxy-8-trifluoromethyl-quinoline derivatives were synthesized through multi step reactions. All the newly synthesized compounds were characterized by spectral and elemental analyses. The structure of 5j was evidenced by X-ray crystallographic study. The newly synthesized title compounds were evaluated for their antimicrobial activities including antimycobacterial activity. Amongst the tested compounds, 5b, 5e, 5h, 5j, 6c and 7c displayed promising antimicrobial activity. The mode of action of these active compounds was carried out by docking of receptor enoyl-ACP reductase with newly synthesized candidate ligands, 5b, 5e, 5h, 5j and 6c.
Three new series of 4-hydroxy-8-trifluoromethyl-quinoline derivatives were synthesized and the most effective compounds have a MIC value of 0.625μg/mL against Mycobacterium tuberculosis H37Rv. [Display omitted]
▸New series of quinoline carbohydrazone derivatives were synthesized. ▸X-ray crystallographic study of the title compound 5j was carried out. ▸In vitro antibacterial and antimycobacterial screening were carried out. ▸Compounds 5b, 5e, 5h, 5j and 6c showed substantial antitubercular activity. ▸Docking studies were carried out.</description><subject>Antibacterial</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antimycobacterial</subject><subject>Antitubercular Agents - chemical synthesis</subject><subject>Antitubercular Agents - chemistry</subject><subject>Antitubercular Agents - pharmacology</subject><subject>Bacteria - drug effects</subject><subject>Biological and medical sciences</subject><subject>Docking study</subject><subject>Drug Design</subject><subject>Hydrazines - chemical synthesis</subject><subject>Hydrazines - chemistry</subject><subject>Hydrazines - pharmacology</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinoline</subject><subject>Quinolines - chemistry</subject><subject>X-ray crystallography</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE2P0zAQhi0EYsvCP0DIF8SFhPFH7PSChJZPaSUucLYce9K6pM6u7RSVX4-rFrhxmhnpmZlXDyHPGbQMmHqza3G3R7dtOTDWgm5BiAdkxbTqG8E7-ZCsgHPRdFzIK_Ik5x0AdArgMbnibA1aKrUi03vMYRNf03yMZVv7TG301M_uR4gbmsviA2Y6jzTiT3q_hDhPIWIjGmfTMG-PPtlfwSP1mMLBlnCotD0dKaEsAya3TDZRu8FY8lPyaLRTxmeXek2-f_zw7eZzc_v105ebd7eNk50ujR4FDL0cet0JMWqrkFmm6ghrGDslNe8E597V0jPVoegl43yoGqRdDwDimrw6371L8_2CuZh9yA6nyUacl2zWAEr0WrNKyjPp0pxzwtHcpbC36WgYmJNmszNnzeak2YA2VXNde3F5sAx79H-X_nitwMsLYLOz05hsdCH_46QWAPyU9O2Zw6rjEDCZ7AJGhz4kdMX4Ofw_yW8hZ5zO</recordid><startdate>20111101</startdate><enddate>20111101</enddate><creator>Thomas, K.D.</creator><creator>Adhikari, Airody Vasudeva</creator><creator>Telkar, Sandeep</creator><creator>Chowdhury, Imran H.</creator><creator>Mahmood, Riaz</creator><creator>Pal, Nishith K.</creator><creator>Row, Guru</creator><creator>Sumesh, E.</creator><general>Elsevier Masson SAS</general><general>Elsevier</general><scope>IQODW</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></search><sort><creationdate>20111101</creationdate><title>Design, synthesis and docking studies of new quinoline-3-carbohydrazide derivatives as antitubercular agents</title><author>Thomas, K.D. ; Adhikari, Airody Vasudeva ; Telkar, Sandeep ; Chowdhury, Imran H. ; Mahmood, Riaz ; Pal, Nishith K. ; Row, Guru ; Sumesh, E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c457t-7f30b84b87533f7a6e1a16b87090f564725322dc2538165e384122b0114a9b003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Antibacterial</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antimycobacterial</topic><topic>Antitubercular Agents - chemical synthesis</topic><topic>Antitubercular Agents - chemistry</topic><topic>Antitubercular Agents - pharmacology</topic><topic>Bacteria - drug effects</topic><topic>Biological and medical sciences</topic><topic>Docking study</topic><topic>Drug Design</topic><topic>Hydrazines - chemical synthesis</topic><topic>Hydrazines - chemistry</topic><topic>Hydrazines - pharmacology</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinoline</topic><topic>Quinolines - chemistry</topic><topic>X-ray crystallography</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Thomas, K.D.</creatorcontrib><creatorcontrib>Adhikari, Airody Vasudeva</creatorcontrib><creatorcontrib>Telkar, Sandeep</creatorcontrib><creatorcontrib>Chowdhury, Imran H.</creatorcontrib><creatorcontrib>Mahmood, Riaz</creatorcontrib><creatorcontrib>Pal, Nishith K.</creatorcontrib><creatorcontrib>Row, Guru</creatorcontrib><creatorcontrib>Sumesh, E.</creatorcontrib><collection>Pascal-Francis</collection><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>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Thomas, K.D.</au><au>Adhikari, Airody Vasudeva</au><au>Telkar, Sandeep</au><au>Chowdhury, Imran H.</au><au>Mahmood, Riaz</au><au>Pal, Nishith K.</au><au>Row, Guru</au><au>Sumesh, E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis and docking studies of new quinoline-3-carbohydrazide derivatives as antitubercular agents</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2011-11-01</date><risdate>2011</risdate><volume>46</volume><issue>11</issue><spage>5283</spage><epage>5292</epage><pages>5283-5292</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Three new series of 4-hydroxy-8-trifluoromethyl-quinoline derivatives were synthesized through multi step reactions. All the newly synthesized compounds were characterized by spectral and elemental analyses. The structure of 5j was evidenced by X-ray crystallographic study. The newly synthesized title compounds were evaluated for their antimicrobial activities including antimycobacterial activity. Amongst the tested compounds, 5b, 5e, 5h, 5j, 6c and 7c displayed promising antimicrobial activity. The mode of action of these active compounds was carried out by docking of receptor enoyl-ACP reductase with newly synthesized candidate ligands, 5b, 5e, 5h, 5j and 6c.
Three new series of 4-hydroxy-8-trifluoromethyl-quinoline derivatives were synthesized and the most effective compounds have a MIC value of 0.625μg/mL against Mycobacterium tuberculosis H37Rv. [Display omitted]
▸New series of quinoline carbohydrazone derivatives were synthesized. ▸X-ray crystallographic study of the title compound 5j was carried out. ▸In vitro antibacterial and antimycobacterial screening were carried out. ▸Compounds 5b, 5e, 5h, 5j and 6c showed substantial antitubercular activity. ▸Docking studies were carried out.</abstract><cop>Kidlington</cop><pub>Elsevier Masson SAS</pub><pmid>21907466</pmid><doi>10.1016/j.ejmech.2011.07.033</doi><tpages>10</tpages></addata></record> |
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| subjects | Antibacterial Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Antimycobacterial Antitubercular Agents - chemical synthesis Antitubercular Agents - chemistry Antitubercular Agents - pharmacology Bacteria - drug effects Biological and medical sciences Docking study Drug Design Hydrazines - chemical synthesis Hydrazines - chemistry Hydrazines - pharmacology Medical sciences Microbial Sensitivity Tests Models, Molecular Molecular Conformation Pharmacology. Drug treatments Quinoline Quinolines - chemistry X-ray crystallography |
| title | Design, synthesis and docking studies of new quinoline-3-carbohydrazide derivatives as antitubercular agents |
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