Synthesis and evaluation of analogues of congo red as potential compounds against transmissible spongiform encephalopathies
The synthesis of analogues of the amyloid stain Congo red ( 1) as potential compounds against transmissible spongiform encephalopathies (TSEs) is reported. Using the direct method, aniline ( 2) or diamines such as 4,4′-diaminodiphenylsulfone (dapsone, 9), 3,3′-diaminodiphenylsulfone ( 10), benzidine...
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| Veröffentlicht in: | European journal of medicinal chemistry 2003-06, Vol.38 (6), p.567-579 |
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| container_title | European journal of medicinal chemistry |
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| creator | Rudyk, Hélène Knaggs, Michael H Vasiljevic, Snezana Hope, James Birkett, Chris Gilbert, Ian H |
| description | The synthesis of analogues of the amyloid stain Congo red (
1) as potential compounds against transmissible spongiform encephalopathies (TSEs) is reported. Using the direct method, aniline (
2) or diamines such as 4,4′-diaminodiphenylsulfone (dapsone,
9), 3,3′-diaminodiphenylsulfone (
10), benzidine (
11), 3,3′-dimethoxybenzidine (
12) or 3,3′-dichlorobenzidine (
13) were diazotised to afford the corresponding diazonium salts, which without isolation, were directly used for coupling with a range of aromatic sulfonic or carboxylic acids to provide the corresponding truncated dyes analogues of Congo red,
4,
6,
8, and the symmetrical bis azoic dyes
14–
19,
21–
22,
24 and
26–
29 as their sodium salts. Compounds were assayed in a cellular model of scrapie, a sheep TSE. Some of the compounds were shown to have similar activity to the lead compound Congo red. Molecular modelling was carried out to investigate potential structure-activity relationships (SARs) relating to the size and shape of Congo Red analogues. Within the range of compounds tested no discernible SARs were found. |
| doi_str_mv | 10.1016/S0223-5234(03)00081-3 |
| format | Article |
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1) as potential compounds against transmissible spongiform encephalopathies (TSEs) is reported. Using the direct method, aniline (
2) or diamines such as 4,4′-diaminodiphenylsulfone (dapsone,
9), 3,3′-diaminodiphenylsulfone (
10), benzidine (
11), 3,3′-dimethoxybenzidine (
12) or 3,3′-dichlorobenzidine (
13) were diazotised to afford the corresponding diazonium salts, which without isolation, were directly used for coupling with a range of aromatic sulfonic or carboxylic acids to provide the corresponding truncated dyes analogues of Congo red,
4,
6,
8, and the symmetrical bis azoic dyes
14–
19,
21–
22,
24 and
26–
29 as their sodium salts. Compounds were assayed in a cellular model of scrapie, a sheep TSE. Some of the compounds were shown to have similar activity to the lead compound Congo red. Molecular modelling was carried out to investigate potential structure-activity relationships (SARs) relating to the size and shape of Congo Red analogues. Within the range of compounds tested no discernible SARs were found.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/S0223-5234(03)00081-3</identifier><identifier>PMID: 12832128</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>Amino Acids - chemistry ; Animals ; Azo dyes ; Biological and medical sciences ; Congo Red - analogs & derivatives ; Congo Red - chemical synthesis ; Congo Red - pharmacology ; Medical sciences ; Miscellaneous ; Monte Carlo Method ; Neuropharmacology ; Pharmacology. Drug treatments ; Prion Diseases - drug therapy ; Prions ; PrPC Proteins - metabolism ; Sheep ; TSE</subject><ispartof>European journal of medicinal chemistry, 2003-06, Vol.38 (6), p.567-579</ispartof><rights>2003 Éditions scientifiques et médicales Elsevier SAS</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c391t-bb0f3b41f1e030510736e4cba8645e56445270232d2c37437fce8f4e1ad9124a3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0223-5234(03)00081-3$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14938334$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12832128$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rudyk, Hélène</creatorcontrib><creatorcontrib>Knaggs, Michael H</creatorcontrib><creatorcontrib>Vasiljevic, Snezana</creatorcontrib><creatorcontrib>Hope, James</creatorcontrib><creatorcontrib>Birkett, Chris</creatorcontrib><creatorcontrib>Gilbert, Ian H</creatorcontrib><title>Synthesis and evaluation of analogues of congo red as potential compounds against transmissible spongiform encephalopathies</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>The synthesis of analogues of the amyloid stain Congo red (
1) as potential compounds against transmissible spongiform encephalopathies (TSEs) is reported. Using the direct method, aniline (
2) or diamines such as 4,4′-diaminodiphenylsulfone (dapsone,
9), 3,3′-diaminodiphenylsulfone (
10), benzidine (
11), 3,3′-dimethoxybenzidine (
12) or 3,3′-dichlorobenzidine (
13) were diazotised to afford the corresponding diazonium salts, which without isolation, were directly used for coupling with a range of aromatic sulfonic or carboxylic acids to provide the corresponding truncated dyes analogues of Congo red,
4,
6,
8, and the symmetrical bis azoic dyes
14–
19,
21–
22,
24 and
26–
29 as their sodium salts. Compounds were assayed in a cellular model of scrapie, a sheep TSE. Some of the compounds were shown to have similar activity to the lead compound Congo red. Molecular modelling was carried out to investigate potential structure-activity relationships (SARs) relating to the size and shape of Congo Red analogues. Within the range of compounds tested no discernible SARs were found.</description><subject>Amino Acids - chemistry</subject><subject>Animals</subject><subject>Azo dyes</subject><subject>Biological and medical sciences</subject><subject>Congo Red - analogs & derivatives</subject><subject>Congo Red - chemical synthesis</subject><subject>Congo Red - pharmacology</subject><subject>Medical sciences</subject><subject>Miscellaneous</subject><subject>Monte Carlo Method</subject><subject>Neuropharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Prion Diseases - drug therapy</subject><subject>Prions</subject><subject>PrPC Proteins - metabolism</subject><subject>Sheep</subject><subject>TSE</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v1DAQhi0EotvCTwD5AiqHgO1xPvZUoYovqRKHwtlynMmuUWIHj1Op4s_j7a7okYstj553Zvww9kqK91LI5sOtUAqqWoG-FPBOCNHJCp6wjWybrgJV66ds8w85Y-dEvwpUN0I8Z2dSdaDKsWF_bu9D3iN54jYMHO_stNrsY-BxLBU7xd2KdHi4GHaRJxy4Jb7EjCF7O5XyvMQ1DCW_sz5Q5jnZQLMn8v2EnJaS82NMM8fgcNmXlovNe4_0gj0b7UT48nRfsJ-fP_24_lrdfP_y7frjTeVgK3PV92KEXstRogBRS9FCg9r1tmt0jXWjda1aoUANykGroR0ddqNGaYetVNrCBXt77Luk-Lv8JpuyncNpsgHjSqYFLXTT1QWsj6BLkSjhaJbkZ5vujRTmYN08WDcHpUaAebBuoORenwas_YzDY-qkuQBvToAlZ6exGHKeHjm9hQ5AF-7qyGHRcecxGXL-oG3wCV02Q_T_WeUvq8Kgtw</recordid><startdate>20030601</startdate><enddate>20030601</enddate><creator>Rudyk, Hélène</creator><creator>Knaggs, Michael H</creator><creator>Vasiljevic, Snezana</creator><creator>Hope, James</creator><creator>Birkett, Chris</creator><creator>Gilbert, Ian H</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>20030601</creationdate><title>Synthesis and evaluation of analogues of congo red as potential compounds against transmissible spongiform encephalopathies</title><author>Rudyk, Hélène ; Knaggs, Michael H ; Vasiljevic, Snezana ; Hope, James ; Birkett, Chris ; Gilbert, Ian H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c391t-bb0f3b41f1e030510736e4cba8645e56445270232d2c37437fce8f4e1ad9124a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Amino Acids - chemistry</topic><topic>Animals</topic><topic>Azo dyes</topic><topic>Biological and medical sciences</topic><topic>Congo Red - analogs & derivatives</topic><topic>Congo Red - chemical synthesis</topic><topic>Congo Red - pharmacology</topic><topic>Medical sciences</topic><topic>Miscellaneous</topic><topic>Monte Carlo Method</topic><topic>Neuropharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Prion Diseases - drug therapy</topic><topic>Prions</topic><topic>PrPC Proteins - metabolism</topic><topic>Sheep</topic><topic>TSE</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rudyk, Hélène</creatorcontrib><creatorcontrib>Knaggs, Michael H</creatorcontrib><creatorcontrib>Vasiljevic, Snezana</creatorcontrib><creatorcontrib>Hope, James</creatorcontrib><creatorcontrib>Birkett, Chris</creatorcontrib><creatorcontrib>Gilbert, Ian H</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>Rudyk, Hélène</au><au>Knaggs, Michael H</au><au>Vasiljevic, Snezana</au><au>Hope, James</au><au>Birkett, Chris</au><au>Gilbert, Ian H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and evaluation of analogues of congo red as potential compounds against transmissible spongiform encephalopathies</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2003-06-01</date><risdate>2003</risdate><volume>38</volume><issue>6</issue><spage>567</spage><epage>579</epage><pages>567-579</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>The synthesis of analogues of the amyloid stain Congo red (
1) as potential compounds against transmissible spongiform encephalopathies (TSEs) is reported. Using the direct method, aniline (
2) or diamines such as 4,4′-diaminodiphenylsulfone (dapsone,
9), 3,3′-diaminodiphenylsulfone (
10), benzidine (
11), 3,3′-dimethoxybenzidine (
12) or 3,3′-dichlorobenzidine (
13) were diazotised to afford the corresponding diazonium salts, which without isolation, were directly used for coupling with a range of aromatic sulfonic or carboxylic acids to provide the corresponding truncated dyes analogues of Congo red,
4,
6,
8, and the symmetrical bis azoic dyes
14–
19,
21–
22,
24 and
26–
29 as their sodium salts. Compounds were assayed in a cellular model of scrapie, a sheep TSE. Some of the compounds were shown to have similar activity to the lead compound Congo red. Molecular modelling was carried out to investigate potential structure-activity relationships (SARs) relating to the size and shape of Congo Red analogues. Within the range of compounds tested no discernible SARs were found.</abstract><cop>Oxford</cop><pub>Elsevier Masson SAS</pub><pmid>12832128</pmid><doi>10.1016/S0223-5234(03)00081-3</doi><tpages>13</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0223-5234 |
| ispartof | European journal of medicinal chemistry, 2003-06, Vol.38 (6), p.567-579 |
| issn | 0223-5234 1768-3254 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_73404685 |
| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Amino Acids - chemistry Animals Azo dyes Biological and medical sciences Congo Red - analogs & derivatives Congo Red - chemical synthesis Congo Red - pharmacology Medical sciences Miscellaneous Monte Carlo Method Neuropharmacology Pharmacology. Drug treatments Prion Diseases - drug therapy Prions PrPC Proteins - metabolism Sheep TSE |
| title | Synthesis and evaluation of analogues of congo red as potential compounds against transmissible spongiform encephalopathies |
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