On the search for potential anti-Trypanosoma cruzi drugs: Synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions

Five 2-hydroxy-3-substituted-aminomethyl naphthoquinones, nine 1,2,3-triazolic para-naphthoquinones, five nor-β-lapachone-based 1,2,3-triazoles, and several other naphthoquinonoid compounds were synthesized and evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological ag...

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Veröffentlicht in:	European journal of medicinal chemistry 2012-06, Vol.52, p.304-312
Hauptverfasser:	da Silva, Eufrânio N., de Melo, Isadora M.M., Diogo, Emilay B.T., Costa, Verenice A., de Souza Filho, José D., Valença, Wagner O., Camara, Celso A., de Oliveira, Ronaldo N., de Araujo, Alexandre S., Emery, Flávio S., dos Santos, Marcelo R., de Simone, Carlos A., Menna-Barreto, Rubem F.S., de Castro, Solange L.
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Sprache:	eng
Schlagworte:	Animals Biological and medical sciences Chagas disease Chemistry Techniques, Synthetic Chemotherapy Click Chemistry Drug Discovery Lapachol Medical sciences Mice Miscellaneous Naphthoquinones Naphthoquinones - chemical synthesis Naphthoquinones - chemistry Naphthoquinones - pharmacology Naphthoquinones - toxicity Pharmacology. Drug treatments Triazoles - chemistry Trypanocidal Agents - chemical synthesis Trypanocidal Agents - chemistry Trypanocidal Agents - pharmacology Trypanocidal Agents - toxicity Trypanosoma cruzi Trypanosoma cruzi - drug effects
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container_title	European journal of medicinal chemistry
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creator	da Silva, Eufrânio N. de Melo, Isadora M.M. Diogo, Emilay B.T. Costa, Verenice A. de Souza Filho, José D. Valença, Wagner O. Camara, Celso A. de Oliveira, Ronaldo N. de Araujo, Alexandre S. Emery, Flávio S. dos Santos, Marcelo R. de Simone, Carlos A. Menna-Barreto, Rubem F.S. de Castro, Solange L.
description	Five 2-hydroxy-3-substituted-aminomethyl naphthoquinones, nine 1,2,3-triazolic para-naphthoquinones, five nor-β-lapachone-based 1,2,3-triazoles, and several other naphthoquinonoid compounds were synthesized and evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease, continuing our screening program for new trypanocidal compounds. Among all the substances, 16–18, 23, 25–29 and 30–33 were herein described for the first time and fifteen substances were identified as more potent than the standard drug benznidazole, with IC50/24h values in the range of 10.9–101.5μM. Compounds 14 and 19 with Selectivity Index of 18.9 and 6.1 are important structures for further studies. [Display omitted] ► Naphthoquinones-based 1,2,3-triazoles were obtained with trypanocidal activity. ► Quinonoid compounds against the infective bloodstream form of Trypanosoma cruzi were developed. ► Fifteen substances were more active than the anti-T. cruzi drug benznidazole. ► Fifteen compounds were described with IC50/24h values in the range of 10.9–101.5μM.
doi_str_mv	10.1016/j.ejmech.2012.03.039
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Among all the substances, 16–18, 23, 25–29 and 30–33 were herein described for the first time and fifteen substances were identified as more potent than the standard drug benznidazole, with IC50/24h values in the range of 10.9–101.5μM. Compounds 14 and 19 with Selectivity Index of 18.9 and 6.1 are important structures for further studies. 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[Display omitted] ► Naphthoquinones-based 1,2,3-triazoles were obtained with trypanocidal activity. ► Quinonoid compounds against the infective bloodstream form of Trypanosoma cruzi were developed. ► Fifteen substances were more active than the anti-T. cruzi drug benznidazole. ► Fifteen compounds were described with IC50/24h values in the range of 10.9–101.5μM.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Chagas disease</subject><subject>Chemistry Techniques, Synthetic</subject><subject>Chemotherapy</subject><subject>Click Chemistry</subject><subject>Drug Discovery</subject><subject>Lapachol</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Miscellaneous</subject><subject>Naphthoquinones</subject><subject>Naphthoquinones - chemical synthesis</subject><subject>Naphthoquinones - chemistry</subject><subject>Naphthoquinones - pharmacology</subject><subject>Naphthoquinones - toxicity</subject><subject>Pharmacology. Drug treatments</subject><subject>Triazoles - chemistry</subject><subject>Trypanocidal Agents - chemical synthesis</subject><subject>Trypanocidal Agents - chemistry</subject><subject>Trypanocidal Agents - pharmacology</subject><subject>Trypanocidal Agents - toxicity</subject><subject>Trypanosoma cruzi</subject><subject>Trypanosoma cruzi - drug effects</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc2K1EAUhYMoTjv6BiK1EVxM2vpNV1wIMvgHA7NwXIdK5WZSbVIVqyqDmXf0nbxtt7oTLtzNd-453FMUzxndMsqq1_st7Ceww5ZTxrdU4NQPig3bVboUXMmHxYZyLkrFhTwrnqS0p5SqitLHxRnnUotKiE3x89qTPABJYKIdSB8imUMGn50ZicFV3sR1Nj6kMBli43LvSBeX2_SGfFk9KpNLyHWkdWEMt86iDO7MuJjsgiehJ7wc1i6GH2spygnysI5mcj78FrELfiHKHJ25D6OzxJt5yEP4viDgOjxlwzSHxXeJhDYb5wGNVmKR_UbsAJNLOa4kgrEHu_S0eNSbMcGz0z4vvn54f3P5qby6_vj58t1VaUXNc6ks04b1ku1krVRbt1IJK2XLZdsL1WtjW60rxhn0dWdUC5xb0SHIqNz1Wojz4tXx7hwxLKTcYBIL42g8hCU1WFBdManVDlF5RG0MKUXomzm6ycQVoQNXNfvmWGRzKLKhAqdG2YuTw9JO0P0V_WkOgZcnwCR8eh-Nty7945SuNNsp5N4eOcB_3DmITbIOvIXORbC56YL7f5JfEUTCiQ</recordid><startdate>20120601</startdate><enddate>20120601</enddate><creator>da Silva, Eufrânio N.</creator><creator>de Melo, Isadora M.M.</creator><creator>Diogo, Emilay B.T.</creator><creator>Costa, Verenice A.</creator><creator>de Souza Filho, José D.</creator><creator>Valença, Wagner O.</creator><creator>Camara, Celso A.</creator><creator>de Oliveira, Ronaldo N.</creator><creator>de Araujo, Alexandre S.</creator><creator>Emery, Flávio S.</creator><creator>dos Santos, Marcelo R.</creator><creator>de Simone, Carlos A.</creator><creator>Menna-Barreto, Rubem F.S.</creator><creator>de Castro, Solange L.</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>20120601</creationdate><title>On the search for potential anti-Trypanosoma cruzi drugs: Synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions</title><author>da Silva, Eufrânio N. ; de Melo, Isadora M.M. ; Diogo, Emilay B.T. ; Costa, Verenice A. ; de Souza Filho, José D. ; Valença, Wagner O. ; Camara, Celso A. ; de Oliveira, Ronaldo N. ; de Araujo, Alexandre S. ; Emery, Flávio S. ; dos Santos, Marcelo R. ; de Simone, Carlos A. ; Menna-Barreto, Rubem F.S. ; de Castro, Solange L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c392t-5c18a1f4174955b9b453c44b24bf35f8acb886121ef9da5be22c3d5b91047f833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Chagas disease</topic><topic>Chemistry Techniques, Synthetic</topic><topic>Chemotherapy</topic><topic>Click Chemistry</topic><topic>Drug Discovery</topic><topic>Lapachol</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Miscellaneous</topic><topic>Naphthoquinones</topic><topic>Naphthoquinones - chemical synthesis</topic><topic>Naphthoquinones - chemistry</topic><topic>Naphthoquinones - pharmacology</topic><topic>Naphthoquinones - toxicity</topic><topic>Pharmacology. Drug treatments</topic><topic>Triazoles - chemistry</topic><topic>Trypanocidal Agents - chemical synthesis</topic><topic>Trypanocidal Agents - chemistry</topic><topic>Trypanocidal Agents - pharmacology</topic><topic>Trypanocidal Agents - toxicity</topic><topic>Trypanosoma cruzi</topic><topic>Trypanosoma cruzi - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>da Silva, Eufrânio N.</creatorcontrib><creatorcontrib>de Melo, Isadora M.M.</creatorcontrib><creatorcontrib>Diogo, Emilay B.T.</creatorcontrib><creatorcontrib>Costa, Verenice A.</creatorcontrib><creatorcontrib>de Souza Filho, José D.</creatorcontrib><creatorcontrib>Valença, Wagner O.</creatorcontrib><creatorcontrib>Camara, Celso A.</creatorcontrib><creatorcontrib>de Oliveira, Ronaldo N.</creatorcontrib><creatorcontrib>de Araujo, Alexandre S.</creatorcontrib><creatorcontrib>Emery, Flávio S.</creatorcontrib><creatorcontrib>dos Santos, Marcelo R.</creatorcontrib><creatorcontrib>de Simone, Carlos A.</creatorcontrib><creatorcontrib>Menna-Barreto, Rubem F.S.</creatorcontrib><creatorcontrib>de Castro, Solange L.</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>da Silva, Eufrânio N.</au><au>de Melo, Isadora M.M.</au><au>Diogo, Emilay B.T.</au><au>Costa, Verenice A.</au><au>de Souza Filho, José D.</au><au>Valença, Wagner O.</au><au>Camara, Celso A.</au><au>de Oliveira, Ronaldo N.</au><au>de Araujo, Alexandre S.</au><au>Emery, Flávio S.</au><au>dos Santos, Marcelo R.</au><au>de Simone, Carlos A.</au><au>Menna-Barreto, Rubem F.S.</au><au>de Castro, Solange L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>On the search for potential anti-Trypanosoma cruzi drugs: Synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2012-06-01</date><risdate>2012</risdate><volume>52</volume><spage>304</spage><epage>312</epage><pages>304-312</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Five 2-hydroxy-3-substituted-aminomethyl naphthoquinones, nine 1,2,3-triazolic para-naphthoquinones, five nor-β-lapachone-based 1,2,3-triazoles, and several other naphthoquinonoid compounds were synthesized and evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease, continuing our screening program for new trypanocidal compounds. Among all the substances, 16–18, 23, 25–29 and 30–33 were herein described for the first time and fifteen substances were identified as more potent than the standard drug benznidazole, with IC50/24h values in the range of 10.9–101.5μM. Compounds 14 and 19 with Selectivity Index of 18.9 and 6.1 are important structures for further studies. [Display omitted] ► Naphthoquinones-based 1,2,3-triazoles were obtained with trypanocidal activity. ► Quinonoid compounds against the infective bloodstream form of Trypanosoma cruzi were developed. ► Fifteen substances were more active than the anti-T. cruzi drug benznidazole. ► Fifteen compounds were described with IC50/24h values in the range of 10.9–101.5μM.</abstract><cop>Kidlington</cop><pub>Elsevier Masson SAS</pub><pmid>22483633</pmid><doi>10.1016/j.ejmech.2012.03.039</doi><tpages>9</tpages></addata></record>
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subjects	Animals Biological and medical sciences Chagas disease Chemistry Techniques, Synthetic Chemotherapy Click Chemistry Drug Discovery Lapachol Medical sciences Mice Miscellaneous Naphthoquinones Naphthoquinones - chemical synthesis Naphthoquinones - chemistry Naphthoquinones - pharmacology Naphthoquinones - toxicity Pharmacology. Drug treatments Triazoles - chemistry Trypanocidal Agents - chemical synthesis Trypanocidal Agents - chemistry Trypanocidal Agents - pharmacology Trypanocidal Agents - toxicity Trypanosoma cruzi Trypanosoma cruzi - drug effects
title	On the search for potential anti-Trypanosoma cruzi drugs: Synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions
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