Synthesis of new praziquantel analogues: Potential candidates for the treatment of schistosomiasis
An efficient synthesis of antischistosomal drug praziquantel and analogues was achieved and the synthetic route designed was to afford structurally diverse analogues for better structure–activity relationship understanding. Total of nineteen PZQ analogues with structural variations at amide, piperaz...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2012-01, Vol.22 (2), p.1103-1106 |
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| container_end_page | 1106 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Sadhu, Partha Sarathi Kumar, Singam Naveen Chandrasekharam, Malapaka Pica-Mattoccia, Livia Cioli, Donato Rao, Vaidya Jayathirtha |
| description | An efficient synthesis of antischistosomal drug praziquantel and analogues was achieved and the synthetic route designed was to afford structurally diverse analogues for better structure–activity relationship understanding. Total of nineteen PZQ analogues with structural variations at amide, piperazine and aromatic moieties have been synthesized and fully characterized. Among all the new analogues tested for antischistosomal activity, one dimethoxy tetrahydroisoquinoline analogue and two tetrahydro-β-carboline analogues exhibited moderate activity against adult Schistosoma mansoni. Tetrahydro-β-carboline analogues showed moderate activity whereas the presence of p-trifluoromethylbenzoyl and p-toluenesulphonyl moieties resulted in complete suppression of antischistosomal activity. |
| doi_str_mv | 10.1016/j.bmcl.2011.11.108 |
| format | Article |
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Total of nineteen PZQ analogues with structural variations at amide, piperazine and aromatic moieties have been synthesized and fully characterized. Among all the new analogues tested for antischistosomal activity, one dimethoxy tetrahydroisoquinoline analogue and two tetrahydro-β-carboline analogues exhibited moderate activity against adult Schistosoma mansoni. Tetrahydro-β-carboline analogues showed moderate activity whereas the presence of p-trifluoromethylbenzoyl and p-toluenesulphonyl moieties resulted in complete suppression of antischistosomal activity.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2011.11.108</identifier><identifier>PMID: 22217873</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>adults ; Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiparasitic agents ; Antischistosomal ; Biological and medical sciences ; Dose-Response Relationship, Drug ; Drug Design ; drugs ; Medical sciences ; Molecular Structure ; Pharmacology. Drug treatments ; piperazine ; praziquantel ; Praziquantel - chemical synthesis ; Praziquantel - chemistry ; Praziquantel - therapeutic use ; Praziquantel analogues ; Schistosoma mansoni ; Schistosoma mansoni - drug effects ; Schistosomiasis ; Schistosomiasis - drug therapy ; Schistosomicides - chemical synthesis ; Schistosomicides - chemistry ; Schistosomicides - therapeutic use ; Stereoisomerism ; Structure-Activity Relationship ; structure-activity relationships</subject><ispartof>Bioorganic & medicinal chemistry letters, 2012-01, Vol.22 (2), p.1103-1106</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c441t-2fed28ce4dd2f95ac6fc480c03374126f37a61e2aae8ac97407b4af6a08cfb2f3</citedby><cites>FETCH-LOGICAL-c441t-2fed28ce4dd2f95ac6fc480c03374126f37a61e2aae8ac97407b4af6a08cfb2f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X11016520$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25440142$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22217873$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sadhu, Partha Sarathi</creatorcontrib><creatorcontrib>Kumar, Singam Naveen</creatorcontrib><creatorcontrib>Chandrasekharam, Malapaka</creatorcontrib><creatorcontrib>Pica-Mattoccia, Livia</creatorcontrib><creatorcontrib>Cioli, Donato</creatorcontrib><creatorcontrib>Rao, Vaidya Jayathirtha</creatorcontrib><title>Synthesis of new praziquantel analogues: Potential candidates for the treatment of schistosomiasis</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>An efficient synthesis of antischistosomal drug praziquantel and analogues was achieved and the synthetic route designed was to afford structurally diverse analogues for better structure–activity relationship understanding. Total of nineteen PZQ analogues with structural variations at amide, piperazine and aromatic moieties have been synthesized and fully characterized. Among all the new analogues tested for antischistosomal activity, one dimethoxy tetrahydroisoquinoline analogue and two tetrahydro-β-carboline analogues exhibited moderate activity against adult Schistosoma mansoni. Tetrahydro-β-carboline analogues showed moderate activity whereas the presence of p-trifluoromethylbenzoyl and p-toluenesulphonyl moieties resulted in complete suppression of antischistosomal activity.</description><subject>adults</subject><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiparasitic agents</subject><subject>Antischistosomal</subject><subject>Biological and medical sciences</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Design</subject><subject>drugs</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>piperazine</subject><subject>praziquantel</subject><subject>Praziquantel - chemical synthesis</subject><subject>Praziquantel - chemistry</subject><subject>Praziquantel - therapeutic use</subject><subject>Praziquantel analogues</subject><subject>Schistosoma mansoni</subject><subject>Schistosoma mansoni - drug effects</subject><subject>Schistosomiasis</subject><subject>Schistosomiasis - drug therapy</subject><subject>Schistosomicides - chemical synthesis</subject><subject>Schistosomicides - chemistry</subject><subject>Schistosomicides - therapeutic use</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>structure-activity relationships</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU9r3DAQxUVpaTZpv0APrS8lJ28kWZbs0ksJ_QeBFNJAb2IsjxIttrSRtC3Jp6_MbptbCwNzmN97M8wj5BWja0aZPNush9lMa04ZWy9FuydkxYQUdSNo-5SsaC9p3fXixxE5TmlDKRNUiOfkiHPOVKeaFRmu7n2-xeRSFWzl8Ve1jfDg7nbgM04VeJjCzQ7Tu-pbyOizg6ky4Ec3QsZU2RCrIq9yRMhzmS8uydy6lEMKs4Ni_II8szAlfHnoJ-T608fv51_qi8vPX88_XNRGCJZrbnHknUExjtz2LRhpjeiooU2jBOPSNgokQw6AHZheCaoGAVYC7YwduG1OyOnedxvDXTk569klg9MEHsMu6Z5T1QvZNv8nmWSiV4oWku9JE0NKEa3eRjdDvNeM6iUEvdFLCHoJQS9FuyJ6fbDfDTOOfyV_vl6AtwcAkoHJRvDGpUeuFaJExQv3Zs9ZCBpuYmGur8qmtiTZtF0rC_F-T2B57E-HUSfj0BscXUST9Rjcvy79DZiEsGQ</recordid><startdate>20120115</startdate><enddate>20120115</enddate><creator>Sadhu, Partha Sarathi</creator><creator>Kumar, Singam Naveen</creator><creator>Chandrasekharam, Malapaka</creator><creator>Pica-Mattoccia, Livia</creator><creator>Cioli, Donato</creator><creator>Rao, Vaidya Jayathirtha</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><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><scope>7QO</scope><scope>8FD</scope><scope>C1K</scope><scope>F1W</scope><scope>FR3</scope><scope>H95</scope><scope>H97</scope><scope>L.G</scope><scope>P64</scope></search><sort><creationdate>20120115</creationdate><title>Synthesis of new praziquantel analogues: Potential candidates for the treatment of schistosomiasis</title><author>Sadhu, Partha Sarathi ; Kumar, Singam Naveen ; Chandrasekharam, Malapaka ; Pica-Mattoccia, Livia ; Cioli, Donato ; Rao, Vaidya Jayathirtha</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c441t-2fed28ce4dd2f95ac6fc480c03374126f37a61e2aae8ac97407b4af6a08cfb2f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>adults</topic><topic>Animals</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiparasitic agents</topic><topic>Antischistosomal</topic><topic>Biological and medical sciences</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Design</topic><topic>drugs</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>piperazine</topic><topic>praziquantel</topic><topic>Praziquantel - chemical synthesis</topic><topic>Praziquantel - chemistry</topic><topic>Praziquantel - therapeutic use</topic><topic>Praziquantel analogues</topic><topic>Schistosoma mansoni</topic><topic>Schistosoma mansoni - drug effects</topic><topic>Schistosomiasis</topic><topic>Schistosomiasis - drug therapy</topic><topic>Schistosomicides - chemical synthesis</topic><topic>Schistosomicides - chemistry</topic><topic>Schistosomicides - therapeutic use</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><topic>structure-activity relationships</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sadhu, Partha Sarathi</creatorcontrib><creatorcontrib>Kumar, Singam Naveen</creatorcontrib><creatorcontrib>Chandrasekharam, Malapaka</creatorcontrib><creatorcontrib>Pica-Mattoccia, Livia</creatorcontrib><creatorcontrib>Cioli, Donato</creatorcontrib><creatorcontrib>Rao, Vaidya Jayathirtha</creatorcontrib><collection>AGRIS</collection><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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Engineering Research Database</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sadhu, Partha Sarathi</au><au>Kumar, Singam Naveen</au><au>Chandrasekharam, Malapaka</au><au>Pica-Mattoccia, Livia</au><au>Cioli, Donato</au><au>Rao, Vaidya Jayathirtha</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of new praziquantel analogues: Potential candidates for the treatment of schistosomiasis</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2012-01-15</date><risdate>2012</risdate><volume>22</volume><issue>2</issue><spage>1103</spage><epage>1106</epage><pages>1103-1106</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>An efficient synthesis of antischistosomal drug praziquantel and analogues was achieved and the synthetic route designed was to afford structurally diverse analogues for better structure–activity relationship understanding. Total of nineteen PZQ analogues with structural variations at amide, piperazine and aromatic moieties have been synthesized and fully characterized. Among all the new analogues tested for antischistosomal activity, one dimethoxy tetrahydroisoquinoline analogue and two tetrahydro-β-carboline analogues exhibited moderate activity against adult Schistosoma mansoni. Tetrahydro-β-carboline analogues showed moderate activity whereas the presence of p-trifluoromethylbenzoyl and p-toluenesulphonyl moieties resulted in complete suppression of antischistosomal activity.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>22217873</pmid><doi>10.1016/j.bmcl.2011.11.108</doi><tpages>4</tpages></addata></record> |
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| subjects | adults Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antiparasitic agents Antischistosomal Biological and medical sciences Dose-Response Relationship, Drug Drug Design drugs Medical sciences Molecular Structure Pharmacology. Drug treatments piperazine praziquantel Praziquantel - chemical synthesis Praziquantel - chemistry Praziquantel - therapeutic use Praziquantel analogues Schistosoma mansoni Schistosoma mansoni - drug effects Schistosomiasis Schistosomiasis - drug therapy Schistosomicides - chemical synthesis Schistosomicides - chemistry Schistosomicides - therapeutic use Stereoisomerism Structure-Activity Relationship structure-activity relationships |
| title | Synthesis of new praziquantel analogues: Potential candidates for the treatment of schistosomiasis |
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