Synthesis of 2-Hydrazolyl-4-Thiazolidinones Based on Multicomponent Reactions and Biological Evaluation Against Trypanosoma Cruzi
A series of 18 novel 2-hydrazolyl-4-thiazolidinones-5-carboxylic acids, amides and 5,6-α,β-unsaturated esters were synthesized, and their in vitro activity on cruzipain and T. cruzi epimastigotes was determined. Some agents show activity at 37 μm concentration in the enzyme assay. Computational tool...
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| Veröffentlicht in: | Chemical biology & drug design 2011-03, Vol.77 (3), p.166-172 |
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| creator | Pizzo, Chiara Saiz, Cecilia Talevi, Alan Gavernet, Luciana Palestro, Pablo Bellera, Carolina Blanch, Luis Bruno Benítez, Diego Cazzulo, Juan J Chidichimo, Agustina Wipf, Peter Mahler, S. Graciela |
| description | A series of 18 novel 2-hydrazolyl-4-thiazolidinones-5-carboxylic acids, amides and 5,6-α,β-unsaturated esters were synthesized, and their in vitro activity on cruzipain and T. cruzi epimastigotes was determined. Some agents show activity at 37 μm concentration in the enzyme assay. Computational tools and docking were used to correlate the biological response with the physicochemical parameters of the compounds and their cruzipain inhibitory effects. |
| doi_str_mv | 10.1111/j.1747-0285.2010.01071.x |
| format | Article |
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Computational tools and docking were used to correlate the biological response with the physicochemical parameters of the compounds and their cruzipain inhibitory effects.</description><identifier>ISSN: 1747-0277</identifier><identifier>EISSN: 1747-0285</identifier><identifier>DOI: 10.1111/j.1747-0285.2010.01071.x</identifier><identifier>PMID: 21251233</identifier><language>eng</language><publisher>Oxford, UK: Blackwell Publishing Ltd</publisher><subject>2-hydrazolyl-4-thiazolidinone ; Acetamides - chemical synthesis ; Acetamides - chemistry ; Acetamides - toxicity ; Acids ; amides ; Animals ; Antiprotozoal Agents - chemical synthesis ; Antiprotozoal Agents - chemistry ; Antiprotozoal Agents - toxicity ; Binding Sites ; Catalytic Domain ; Cercopithecus aethiops ; Chagas disease ; Computer applications ; Computer Simulation ; cruzipain ; Cysteine Endopeptidases - chemistry ; Cysteine Endopeptidases - metabolism ; Drug development ; Enzymes ; Epimastigotes ; Esters ; inhibitors ; multicomponent connection reaction ; Quantitative Structure-Activity Relationship ; Thiazolidines - chemistry ; Trypanosoma cruzi ; Trypanosoma cruzi - drug effects ; Trypanosoma cruzi - enzymology ; Vero Cells</subject><ispartof>Chemical biology & drug design, 2011-03, Vol.77 (3), p.166-172</ispartof><rights>2011 John Wiley & Sons A/S</rights><rights>2011 John Wiley & Sons A/S.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4151-3df61599fe15b39fe77362a9abface77ff24300c89ed4335e7d53e47bd5cf5b23</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1111%2Fj.1747-0285.2010.01071.x$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1111%2Fj.1747-0285.2010.01071.x$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21251233$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pizzo, Chiara</creatorcontrib><creatorcontrib>Saiz, Cecilia</creatorcontrib><creatorcontrib>Talevi, Alan</creatorcontrib><creatorcontrib>Gavernet, Luciana</creatorcontrib><creatorcontrib>Palestro, Pablo</creatorcontrib><creatorcontrib>Bellera, Carolina</creatorcontrib><creatorcontrib>Blanch, Luis Bruno</creatorcontrib><creatorcontrib>Benítez, Diego</creatorcontrib><creatorcontrib>Cazzulo, Juan J</creatorcontrib><creatorcontrib>Chidichimo, Agustina</creatorcontrib><creatorcontrib>Wipf, Peter</creatorcontrib><creatorcontrib>Mahler, S. Graciela</creatorcontrib><title>Synthesis of 2-Hydrazolyl-4-Thiazolidinones Based on Multicomponent Reactions and Biological Evaluation Against Trypanosoma Cruzi</title><title>Chemical biology & drug design</title><addtitle>Chem Biol Drug Des</addtitle><description>A series of 18 novel 2-hydrazolyl-4-thiazolidinones-5-carboxylic acids, amides and 5,6-α,β-unsaturated esters were synthesized, and their in vitro activity on cruzipain and T. cruzi epimastigotes was determined. Some agents show activity at 37 μm concentration in the enzyme assay. Computational tools and docking were used to correlate the biological response with the physicochemical parameters of the compounds and their cruzipain inhibitory effects.</description><subject>2-hydrazolyl-4-thiazolidinone</subject><subject>Acetamides - chemical synthesis</subject><subject>Acetamides - chemistry</subject><subject>Acetamides - toxicity</subject><subject>Acids</subject><subject>amides</subject><subject>Animals</subject><subject>Antiprotozoal Agents - chemical synthesis</subject><subject>Antiprotozoal Agents - chemistry</subject><subject>Antiprotozoal Agents - toxicity</subject><subject>Binding Sites</subject><subject>Catalytic Domain</subject><subject>Cercopithecus aethiops</subject><subject>Chagas disease</subject><subject>Computer applications</subject><subject>Computer Simulation</subject><subject>cruzipain</subject><subject>Cysteine Endopeptidases - chemistry</subject><subject>Cysteine Endopeptidases - metabolism</subject><subject>Drug development</subject><subject>Enzymes</subject><subject>Epimastigotes</subject><subject>Esters</subject><subject>inhibitors</subject><subject>multicomponent connection reaction</subject><subject>Quantitative Structure-Activity Relationship</subject><subject>Thiazolidines - chemistry</subject><subject>Trypanosoma cruzi</subject><subject>Trypanosoma cruzi - drug effects</subject><subject>Trypanosoma cruzi - enzymology</subject><subject>Vero Cells</subject><issn>1747-0277</issn><issn>1747-0285</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kV9v0zAUxSMEYmPwFcBv8JLiv3HygrRmY0MqQ6Kd4M26SZzOxbW7OIFmb3xzHDr6iCXrHt_705F1T5IggmcknvebGZFcppjmYkZx7MYryWz_JDk9Dp4etZQnyYsQNhhzLmj-PDmhhApCGTtNfi9H19_pYALyLaLp9dh08ODtaFOeru7MpE1jnHc6oDkE3SDv0OfB9qb2211sux591VD3xruAwDVobrz1a1ODRZc_wQ4wjdD5GowLPVp14w6cD34LqOyGB_MyedaCDfrVYz1Lbj9ersrrdPHl6lN5vkhrTgRJWdNmRBRFq4moWCxSsoxCAVULdXy0LeUM4zovdMMZE1o2gmkuq0bUragoO0veHnx3nb8fdOjV1oRaWwtO-yGoXGQyZ3mWRfLdf0kS14ulyDiO6OtHdKi2ulG7zmyhG9W_BUfgwwH4Zawej3OC1RSk2qgpIzXlpaYg1d8g1V6V84uLSUaD9GBgQq_3RwPofqhMMinUt5sr9X3Bb1akXKrpR28OfAtewbozQd0uozXDpOA05wX7A70Gq1Y</recordid><startdate>201103</startdate><enddate>201103</enddate><creator>Pizzo, Chiara</creator><creator>Saiz, Cecilia</creator><creator>Talevi, Alan</creator><creator>Gavernet, Luciana</creator><creator>Palestro, Pablo</creator><creator>Bellera, Carolina</creator><creator>Blanch, Luis Bruno</creator><creator>Benítez, Diego</creator><creator>Cazzulo, Juan J</creator><creator>Chidichimo, Agustina</creator><creator>Wipf, Peter</creator><creator>Mahler, S. Graciela</creator><general>Blackwell Publishing Ltd</general><scope>FBQ</scope><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>M7N</scope><scope>7X8</scope></search><sort><creationdate>201103</creationdate><title>Synthesis of 2-Hydrazolyl-4-Thiazolidinones Based on Multicomponent Reactions and Biological Evaluation Against Trypanosoma Cruzi</title><author>Pizzo, Chiara ; Saiz, Cecilia ; Talevi, Alan ; Gavernet, Luciana ; Palestro, Pablo ; Bellera, Carolina ; Blanch, Luis Bruno ; Benítez, Diego ; Cazzulo, Juan J ; Chidichimo, Agustina ; Wipf, Peter ; Mahler, S. 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| fulltext | fulltext |
| identifier | ISSN: 1747-0277 |
| ispartof | Chemical biology & drug design, 2011-03, Vol.77 (3), p.166-172 |
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| source | MEDLINE; Access via Wiley Online Library |
| subjects | 2-hydrazolyl-4-thiazolidinone Acetamides - chemical synthesis Acetamides - chemistry Acetamides - toxicity Acids amides Animals Antiprotozoal Agents - chemical synthesis Antiprotozoal Agents - chemistry Antiprotozoal Agents - toxicity Binding Sites Catalytic Domain Cercopithecus aethiops Chagas disease Computer applications Computer Simulation cruzipain Cysteine Endopeptidases - chemistry Cysteine Endopeptidases - metabolism Drug development Enzymes Epimastigotes Esters inhibitors multicomponent connection reaction Quantitative Structure-Activity Relationship Thiazolidines - chemistry Trypanosoma cruzi Trypanosoma cruzi - drug effects Trypanosoma cruzi - enzymology Vero Cells |
| title | Synthesis of 2-Hydrazolyl-4-Thiazolidinones Based on Multicomponent Reactions and Biological Evaluation Against Trypanosoma Cruzi |
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