Synthesis and antiprotozoal activity of nitazoxanide–N-methylbenzimidazole hybrids
A series of a novel hybrid compounds between nitazoxanide and N-methylbenzimidazole were synthesized starting from the corresponding N-methyl-2-nitroanilines. The new hybrid compounds (1–13) were evaluated in vitro against Giardia intestinalis, Entamoeba histolytica, Trichomonas vaginalis. NTZ, MTZ...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2013-12, Vol.23 (24), p.6838-6841 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Soria-Arteche, Olivia Hernández-Campos, Alicia Yépez-Mulia, Lilián Trejo-Soto, Pedro Josué Hernández-Luis, Francisco Gres-Molina, Jorge Maldonado, Luis A. Castillo, Rafael |
| description | A series of a novel hybrid compounds between nitazoxanide and N-methylbenzimidazole were synthesized starting from the corresponding N-methyl-2-nitroanilines. The new hybrid compounds (1–13) were evaluated in vitro against Giardia intestinalis, Entamoeba histolytica, Trichomonas vaginalis. NTZ, MTZ and ABZ were used as drug standards. Experimental evaluations revealed all of the new compounds (1–13) were active and showed strong activity against the three protozoa, particularly with E. histolytica where the IC50 values ranged between 3 and 69nM.
Overall, compounds 2, 5, 7, 8, 9, 11 and 12 stood out with values lower than 87nM for all three protozoa, comparatively better than the reference drugs. |
| doi_str_mv | 10.1016/j.bmcl.2013.10.011 |
| format | Article |
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Overall, compounds 2, 5, 7, 8, 9, 11 and 12 stood out with values lower than 87nM for all three protozoa, comparatively better than the reference drugs.</description><subject>Antiprotozoal Agents - chemical synthesis</subject><subject>Antiprotozoal Agents - chemistry</subject><subject>Antiprotozoal Agents - pharmacology</subject><subject>Benzimidazole</subject><subject>Benzimidazoles - chemical synthesis</subject><subject>Benzimidazoles - chemistry</subject><subject>Benzimidazoles - pharmacology</subject><subject>chemistry</subject><subject>Drug Design</subject><subject>drugs</subject><subject>Entamoeba histolytica</subject><subject>Entamoeba histolytica - drug effects</subject><subject>Eukaryota - drug effects</subject><subject>Giardia intestinalis</subject><subject>Giardia lamblia</subject><subject>Giardia lamblia - drug effects</subject><subject>Hybrid compounds</subject><subject>inhibitory concentration 50</subject><subject>Nitazoxanide</subject><subject>Thiazoles - chemistry</subject><subject>Trichomonas vaginalis</subject><subject>Trichomonas vaginalis - drug effects</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>eNp9kMFO3DAQhq0KVLa0L9BDmyOXLOPY2SQSF4RKi4TgwK7Um-XY465XSQy2FzV74h36hjwJjpZy5DAaaeabX6OPkK8U5hTo4nQzb3vVzQugLA3mQOkHMqN8wXPGoTwgM2gWkNcN_31EPoWwAaAcOP9IjgpOa1ZymJHl3TjENQYbMjnoVNHeexfdzskukyraRxvHzJlssFHu3F85WI3PT_9u8h7jeuxaHHa2tzrtOszWY-utDp_JoZFdwC-v_ZisLn8sL37l17c_ry7Or3PFaoh5a5oGeFUwJU2FDFqjCslMaZpS6wp4WTVMI-ct8ppVrWJU15w2FSKAWfCCHZOTfW56-WGLIYreBoVdJwd02yAmFyUkV3VCiz2qvAvBoxH33vbSj4KCmGyKjZhsisnmNEs209G31_xt26N-O_mvLwHf94CRTsg_3gaxuksJZVLNiopNxNmewOTh0aIXQVkcFGrrUUWhnX3vgxelRZGO</recordid><startdate>20131215</startdate><enddate>20131215</enddate><creator>Soria-Arteche, Olivia</creator><creator>Hernández-Campos, Alicia</creator><creator>Yépez-Mulia, Lilián</creator><creator>Trejo-Soto, Pedro Josué</creator><creator>Hernández-Luis, Francisco</creator><creator>Gres-Molina, Jorge</creator><creator>Maldonado, Luis A.</creator><creator>Castillo, Rafael</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></search><sort><creationdate>20131215</creationdate><title>Synthesis and antiprotozoal activity of nitazoxanide–N-methylbenzimidazole hybrids</title><author>Soria-Arteche, Olivia ; Hernández-Campos, Alicia ; Yépez-Mulia, Lilián ; Trejo-Soto, Pedro Josué ; Hernández-Luis, Francisco ; Gres-Molina, Jorge ; Maldonado, Luis A. ; Castillo, Rafael</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c380t-bf9904723caf7e30bfc2a3f5f95dd7045793de44be4837bc31d84197ee00f6423</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Antiprotozoal Agents - chemical synthesis</topic><topic>Antiprotozoal Agents - chemistry</topic><topic>Antiprotozoal Agents - pharmacology</topic><topic>Benzimidazole</topic><topic>Benzimidazoles - chemical synthesis</topic><topic>Benzimidazoles - chemistry</topic><topic>Benzimidazoles - pharmacology</topic><topic>chemistry</topic><topic>Drug Design</topic><topic>drugs</topic><topic>Entamoeba histolytica</topic><topic>Entamoeba histolytica - drug effects</topic><topic>Eukaryota - drug effects</topic><topic>Giardia intestinalis</topic><topic>Giardia lamblia</topic><topic>Giardia lamblia - drug effects</topic><topic>Hybrid compounds</topic><topic>inhibitory concentration 50</topic><topic>Nitazoxanide</topic><topic>Thiazoles - chemistry</topic><topic>Trichomonas vaginalis</topic><topic>Trichomonas vaginalis - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Soria-Arteche, Olivia</creatorcontrib><creatorcontrib>Hernández-Campos, Alicia</creatorcontrib><creatorcontrib>Yépez-Mulia, Lilián</creatorcontrib><creatorcontrib>Trejo-Soto, Pedro Josué</creatorcontrib><creatorcontrib>Hernández-Luis, Francisco</creatorcontrib><creatorcontrib>Gres-Molina, Jorge</creatorcontrib><creatorcontrib>Maldonado, Luis A.</creatorcontrib><creatorcontrib>Castillo, Rafael</creatorcontrib><collection>AGRIS</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Soria-Arteche, Olivia</au><au>Hernández-Campos, Alicia</au><au>Yépez-Mulia, Lilián</au><au>Trejo-Soto, Pedro Josué</au><au>Hernández-Luis, Francisco</au><au>Gres-Molina, Jorge</au><au>Maldonado, Luis A.</au><au>Castillo, Rafael</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and antiprotozoal activity of nitazoxanide–N-methylbenzimidazole hybrids</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2013-12-15</date><risdate>2013</risdate><volume>23</volume><issue>24</issue><spage>6838</spage><epage>6841</epage><pages>6838-6841</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A series of a novel hybrid compounds between nitazoxanide and N-methylbenzimidazole were synthesized starting from the corresponding N-methyl-2-nitroanilines. The new hybrid compounds (1–13) were evaluated in vitro against Giardia intestinalis, Entamoeba histolytica, Trichomonas vaginalis. NTZ, MTZ and ABZ were used as drug standards. Experimental evaluations revealed all of the new compounds (1–13) were active and showed strong activity against the three protozoa, particularly with E. histolytica where the IC50 values ranged between 3 and 69nM.
Overall, compounds 2, 5, 7, 8, 9, 11 and 12 stood out with values lower than 87nM for all three protozoa, comparatively better than the reference drugs.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>24183540</pmid><doi>10.1016/j.bmcl.2013.10.011</doi><tpages>4</tpages></addata></record> |
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| subjects | Antiprotozoal Agents - chemical synthesis Antiprotozoal Agents - chemistry Antiprotozoal Agents - pharmacology Benzimidazole Benzimidazoles - chemical synthesis Benzimidazoles - chemistry Benzimidazoles - pharmacology chemistry Drug Design drugs Entamoeba histolytica Entamoeba histolytica - drug effects Eukaryota - drug effects Giardia intestinalis Giardia lamblia Giardia lamblia - drug effects Hybrid compounds inhibitory concentration 50 Nitazoxanide Thiazoles - chemistry Trichomonas vaginalis Trichomonas vaginalis - drug effects |
| title | Synthesis and antiprotozoal activity of nitazoxanide–N-methylbenzimidazole hybrids |
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