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Simple oxidation of pyrimidinylhydrazones to triazolopyrimidines and their inhibition of Shiga toxin trafficking
The oxidative cyclisation of a range of benzothieno[2,3- d]pyrimidine hydrazones ( 7a– j) to the 1,2,4-triazolo[4,3- c]pyrimidines ( 8a– j) catalysed by lithium iodide or to the 1,2,4-triazolo[1,5- c]pyrimidines ( 10a– j) with sodium carbonate is presented. A complementary synthesis of the 1,2,4-tri...
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| Published in: | European journal of medicinal chemistry 2010, Vol.45 (1), p.275-283 |
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| Main Authors: | , , , , |
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| cites | cdi_FETCH-LOGICAL-c437t-f54854978a7a1017e885858d04d33353015fe5e8c4313abfcdbf38f2136618133 |
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| container_start_page | 275 |
| container_title | European journal of medicinal chemistry |
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| creator | Guetzoyan, Lucie J. Spooner, Robert A. Lord, J. Michael Roberts, Lynne M. Clarkson, Guy J. |
| description | The oxidative cyclisation of a range of benzothieno[2,3-
d]pyrimidine hydrazones (
7a–
j) to the 1,2,4-triazolo[4,3-
c]pyrimidines (
8a–
j) catalysed by lithium iodide or to the 1,2,4-triazolo[1,5-
c]pyrimidines (
10a–
j) with sodium carbonate is presented. A complementary synthesis of the 1,2,4-triazolo[1,5-
c]pyrimidines starting from the amino imine
11 is also reported. The effect of these compounds on Shiga toxin (STx) trafficking in HeLa cells and comparison to the previously reported Exo2 is also detailed
[Display omitted] |
| doi_str_mv | 10.1016/j.ejmech.2009.10.007 |
| format | article |
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d]pyrimidine hydrazones (
7a–
j) to the 1,2,4-triazolo[4,3-
c]pyrimidines (
8a–
j) catalysed by lithium iodide or to the 1,2,4-triazolo[1,5-
c]pyrimidines (
10a–
j) with sodium carbonate is presented. A complementary synthesis of the 1,2,4-triazolo[1,5-
c]pyrimidines starting from the amino imine
11 is also reported. The effect of these compounds on Shiga toxin (STx) trafficking in HeLa cells and comparison to the previously reported Exo2 is also detailed
[Display omitted]</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2009.10.007</identifier><identifier>PMID: 19883956</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Kidlington: Elsevier Masson SAS</publisher><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents ; Benzaldehydes - chemistry ; Benzaldehydes - pharmacology ; Biological and medical sciences ; Biological Transport - drug effects ; Cyclization ; Dimroth rearrangement ; DMSO ; Exo2 ; General aspects ; HeLa Cells ; Humans ; Hydrazones - chemistry ; Hydrazones - pharmacology ; Lithium iodide ; Medical sciences ; Oxidation-Reduction ; Pharmacology. Drug treatments ; Pyrimidines - chemistry ; Pyrimidines - pharmacology ; Pyrimidyl hydrazone ; Shiga toxin ; Shiga Toxin - metabolism ; Sodium carbonate ; Triazoles - chemistry ; Triazoles - pharmacology ; Triazolopyrimidine</subject><ispartof>European journal of medicinal chemistry, 2010, Vol.45 (1), p.275-283</ispartof><rights>2009 Elsevier Masson SAS</rights><rights>2015 INIST-CNRS</rights><rights>Copyright 2009 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c437t-f54854978a7a1017e885858d04d33353015fe5e8c4313abfcdbf38f2136618133</citedby><cites>FETCH-LOGICAL-c437t-f54854978a7a1017e885858d04d33353015fe5e8c4313abfcdbf38f2136618133</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22375601$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19883956$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Guetzoyan, Lucie J.</creatorcontrib><creatorcontrib>Spooner, Robert A.</creatorcontrib><creatorcontrib>Lord, J. Michael</creatorcontrib><creatorcontrib>Roberts, Lynne M.</creatorcontrib><creatorcontrib>Clarkson, Guy J.</creatorcontrib><title>Simple oxidation of pyrimidinylhydrazones to triazolopyrimidines and their inhibition of Shiga toxin trafficking</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>The oxidative cyclisation of a range of benzothieno[2,3-
d]pyrimidine hydrazones (
7a–
j) to the 1,2,4-triazolo[4,3-
c]pyrimidines (
8a–
j) catalysed by lithium iodide or to the 1,2,4-triazolo[1,5-
c]pyrimidines (
10a–
j) with sodium carbonate is presented. A complementary synthesis of the 1,2,4-triazolo[1,5-
c]pyrimidines starting from the amino imine
11 is also reported. The effect of these compounds on Shiga toxin (STx) trafficking in HeLa cells and comparison to the previously reported Exo2 is also detailed
[Display omitted]</description><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Benzaldehydes - chemistry</subject><subject>Benzaldehydes - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Biological Transport - drug effects</subject><subject>Cyclization</subject><subject>Dimroth rearrangement</subject><subject>DMSO</subject><subject>Exo2</subject><subject>General aspects</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Hydrazones - chemistry</subject><subject>Hydrazones - pharmacology</subject><subject>Lithium iodide</subject><subject>Medical sciences</subject><subject>Oxidation-Reduction</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyrimidines - chemistry</subject><subject>Pyrimidines - pharmacology</subject><subject>Pyrimidyl hydrazone</subject><subject>Shiga toxin</subject><subject>Shiga Toxin - metabolism</subject><subject>Sodium carbonate</subject><subject>Triazoles - chemistry</subject><subject>Triazoles - pharmacology</subject><subject>Triazolopyrimidine</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNp9kUFP3DAQha2KqizQf1ChXFBP2dpxnDiXSghRWgmJA-Vsee0xmSWxUzuLWH59vdot3CofLD99b8bzhpAvjC4ZZc239RLWI5h-WVHaZWlJafuBLFjbyJJXoj4iC1pVvBQVr4_JSUprSqloKP1EjlknJe9EsyDTPY7TAEV4QatnDL4Irpi2EUe06LdDv7VRvwYPqZhDMUfMjyG8AVnW3hZzDxgL9D2u8F-R-x4fdTa9oM8-7RyaJ_SPZ-Sj00OCz4f7lDz8uP599bO8vbv5dXV5W5qat3PpRC1F3bVStzqP24KUIh9La8s5F5wy4UCAzDTjeuWMXTkuXcV40zDJOD8lX_d1pxj-bCDNasRkYBi0h7BJquW8qxopaCbrPWliSCmCU1OeTsetYlTtolZrtY9a7aLeqTnqbDs_NNisRrDvpkO2Gbg4ADoZPbiovcH0xuXdtHkdLHPf9xzkOJ4RokoGwRuwGMHMygb8_0_-AofuoCQ</recordid><startdate>2010</startdate><enddate>2010</enddate><creator>Guetzoyan, Lucie J.</creator><creator>Spooner, Robert A.</creator><creator>Lord, J. Michael</creator><creator>Roberts, Lynne M.</creator><creator>Clarkson, Guy J.</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>2010</creationdate><title>Simple oxidation of pyrimidinylhydrazones to triazolopyrimidines and their inhibition of Shiga toxin trafficking</title><author>Guetzoyan, Lucie J. ; Spooner, Robert A. ; Lord, J. Michael ; Roberts, Lynne M. ; Clarkson, Guy J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c437t-f54854978a7a1017e885858d04d33353015fe5e8c4313abfcdbf38f2136618133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Benzaldehydes - chemistry</topic><topic>Benzaldehydes - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Biological Transport - drug effects</topic><topic>Cyclization</topic><topic>Dimroth rearrangement</topic><topic>DMSO</topic><topic>Exo2</topic><topic>General aspects</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Hydrazones - chemistry</topic><topic>Hydrazones - pharmacology</topic><topic>Lithium iodide</topic><topic>Medical sciences</topic><topic>Oxidation-Reduction</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyrimidines - chemistry</topic><topic>Pyrimidines - pharmacology</topic><topic>Pyrimidyl hydrazone</topic><topic>Shiga toxin</topic><topic>Shiga Toxin - metabolism</topic><topic>Sodium carbonate</topic><topic>Triazoles - chemistry</topic><topic>Triazoles - pharmacology</topic><topic>Triazolopyrimidine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Guetzoyan, Lucie J.</creatorcontrib><creatorcontrib>Spooner, Robert A.</creatorcontrib><creatorcontrib>Lord, J. Michael</creatorcontrib><creatorcontrib>Roberts, Lynne M.</creatorcontrib><creatorcontrib>Clarkson, Guy J.</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>Guetzoyan, Lucie J.</au><au>Spooner, Robert A.</au><au>Lord, J. Michael</au><au>Roberts, Lynne M.</au><au>Clarkson, Guy J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Simple oxidation of pyrimidinylhydrazones to triazolopyrimidines and their inhibition of Shiga toxin trafficking</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2010</date><risdate>2010</risdate><volume>45</volume><issue>1</issue><spage>275</spage><epage>283</epage><pages>275-283</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>The oxidative cyclisation of a range of benzothieno[2,3-
d]pyrimidine hydrazones (
7a–
j) to the 1,2,4-triazolo[4,3-
c]pyrimidines (
8a–
j) catalysed by lithium iodide or to the 1,2,4-triazolo[1,5-
c]pyrimidines (
10a–
j) with sodium carbonate is presented. A complementary synthesis of the 1,2,4-triazolo[1,5-
c]pyrimidines starting from the amino imine
11 is also reported. The effect of these compounds on Shiga toxin (STx) trafficking in HeLa cells and comparison to the previously reported Exo2 is also detailed
[Display omitted]</abstract><cop>Kidlington</cop><pub>Elsevier Masson SAS</pub><pmid>19883956</pmid><doi>10.1016/j.ejmech.2009.10.007</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0223-5234 |
| ispartof | European journal of medicinal chemistry, 2010, Vol.45 (1), p.275-283 |
| issn | 0223-5234 1768-3254 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_733926850 |
| source | ScienceDirect Freedom Collection |
| subjects | Antibiotics. Antiinfectious agents. Antiparasitic agents Benzaldehydes - chemistry Benzaldehydes - pharmacology Biological and medical sciences Biological Transport - drug effects Cyclization Dimroth rearrangement DMSO Exo2 General aspects HeLa Cells Humans Hydrazones - chemistry Hydrazones - pharmacology Lithium iodide Medical sciences Oxidation-Reduction Pharmacology. Drug treatments Pyrimidines - chemistry Pyrimidines - pharmacology Pyrimidyl hydrazone Shiga toxin Shiga Toxin - metabolism Sodium carbonate Triazoles - chemistry Triazoles - pharmacology Triazolopyrimidine |
| title | Simple oxidation of pyrimidinylhydrazones to triazolopyrimidines and their inhibition of Shiga toxin trafficking |
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