Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors
This paper reports the synthesis and evaluation of the biological affinity towards benzodiazepine and A 1 and A 2A adenosine receptors of some 3-ethoxycarbonyl or 3-phenyl-substituted 1,2,3-triazolo[1,5-a]quinazolines. Starting from the appropriate chloro-substituted phenylazides, the series of 7 or...
Gespeichert in:
| Veröffentlicht in: | European journal of medicinal chemistry 2000-03, Vol.35 (3), p.333-341 |
|---|---|
| Hauptverfasser: | , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 341 |
|---|---|
| container_issue | 3 |
| container_start_page | 333 |
| container_title | European journal of medicinal chemistry |
| container_volume | 35 |
| creator | Bertelli, Lucia Biagi, Giuliana Giorgi, Irene Livi, Oreste Manera, Clementina Scartoni, Valerio Lucacchini, Antonio Giannaccini, Gino Barili, Pier Luigi |
| description | This paper reports the synthesis and evaluation of the biological affinity towards benzodiazepine and A
1 and A
2A adenosine receptors of some 3-ethoxycarbonyl or 3-phenyl-substituted 1,2,3-triazolo[1,5-a]quinazolines. Starting from the appropriate chloro-substituted phenylazides, the series of 7 or 8 chloro-substituted triazoloquinazolines were prepared. Nitration reactions of the triazoloquinazoline ring and chlorination reactions of the hydroxyl group in the 5 position of the same ring are also reported. By nucleophilic displacement of halogen, the corresponding 5-amino derivatives and some analogous derivatives bearing cyclohexylamino and
p-toluidino substituents were obtained. The binding assays showed a generalized decrease in the affinity towards the benzodiazepine receptors and confirmed a moderate affinity towards the A
1 adenosine receptors in comparison with the previously studied triazoloquinazoline derivatives. |
| doi_str_mv | 10.1016/S0223-5234(00)90154-5 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_71083138</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0223523400901545</els_id><sourcerecordid>71083138</sourcerecordid><originalsourceid>FETCH-LOGICAL-c456t-304b40fddfa8984ecc31fac2bf521923680b06442ed9e48fe66234cb7aae8db3</originalsourceid><addsrcrecordid>eNqFkE1rFTEUhoMo9rb6E5RZiCjc0ZOvuZluRIq1hYKLdicSMskZjcxNbpNMof31zf1A3bk6vJznzcdDyCsKHyjQ7uM1MMZbybh4B_C-BypFK5-QBV11quVMiqdk8Qc5Isc5_wYA2QE8J0cUVkpK2S9IuJ6HXHyZC7qGLtmStyV58xCn-J0uZWt-3M4-bLMPmE-bfB_KL8w-Nya4ZvDB-fCzKbEZMDxEV5u4qeRuaxyGmLcpocVNiSm_IM9GM2V8eZgn5Ob8y83ZRXv17evl2eer1grZlZaDGASMzo1G9UqgtZyOxrJhlIz2jHcKBuiEYOh6FGrErqu_tMPKGFRu4Cfk7f7YTYq3M-ai1z5bnCYTMM5ZrygoTrmqoNyDNsWcE456k_zapHtNQW89651nvZWoAfTOs5a19_pwwTys0f3T2outwJsDYLI105hMsD7_5TjnPe0q9mmPYZVx5zHpbD0Gi85XZ0W76P_zkkfyKpsl</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>71083138</pqid></control><display><type>article</type><title>Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors</title><source>MEDLINE</source><source>ScienceDirect Journals (5 years ago - present)</source><creator>Bertelli, Lucia ; Biagi, Giuliana ; Giorgi, Irene ; Livi, Oreste ; Manera, Clementina ; Scartoni, Valerio ; Lucacchini, Antonio ; Giannaccini, Gino ; Barili, Pier Luigi</creator><creatorcontrib>Bertelli, Lucia ; Biagi, Giuliana ; Giorgi, Irene ; Livi, Oreste ; Manera, Clementina ; Scartoni, Valerio ; Lucacchini, Antonio ; Giannaccini, Gino ; Barili, Pier Luigi</creatorcontrib><description>This paper reports the synthesis and evaluation of the biological affinity towards benzodiazepine and A
1 and A
2A adenosine receptors of some 3-ethoxycarbonyl or 3-phenyl-substituted 1,2,3-triazolo[1,5-a]quinazolines. Starting from the appropriate chloro-substituted phenylazides, the series of 7 or 8 chloro-substituted triazoloquinazolines were prepared. Nitration reactions of the triazoloquinazoline ring and chlorination reactions of the hydroxyl group in the 5 position of the same ring are also reported. By nucleophilic displacement of halogen, the corresponding 5-amino derivatives and some analogous derivatives bearing cyclohexylamino and
p-toluidino substituents were obtained. The binding assays showed a generalized decrease in the affinity towards the benzodiazepine receptors and confirmed a moderate affinity towards the A
1 adenosine receptors in comparison with the previously studied triazoloquinazoline derivatives.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/S0223-5234(00)90154-5</identifier><identifier>PMID: 10785559</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>1,2,3-triazoles ; 1,2,3-triazolo[1,5-a]quinazolines ; A 1 and A 2A adenosine receptor binding ; Animals ; benzodiazepine receptor binding ; Binding, Competitive - drug effects ; Biological and medical sciences ; Cattle ; Chemical Phenomena ; Chemistry, Physical ; Gabaergic and benzodiazepinic system ; In Vitro Techniques ; Ligands ; Magnetic Resonance Spectroscopy ; Medical sciences ; Neostriatum - drug effects ; Neostriatum - metabolism ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems ; Pharmacology. Drug treatments ; Quinazolines - chemical synthesis ; Quinazolines - pharmacology ; Receptor, Adenosine A2A ; Receptors, GABA-A - drug effects ; Receptors, Purinergic P1 - drug effects ; Structure-Activity Relationship ; Triazoles - chemical synthesis ; Triazoles - pharmacology</subject><ispartof>European journal of medicinal chemistry, 2000-03, Vol.35 (3), p.333-341</ispartof><rights>2000 Éditions scientifiques et médicales Elsevier SAS</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c456t-304b40fddfa8984ecc31fac2bf521923680b06442ed9e48fe66234cb7aae8db3</citedby><cites>FETCH-LOGICAL-c456t-304b40fddfa8984ecc31fac2bf521923680b06442ed9e48fe66234cb7aae8db3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0223-5234(00)90154-5$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3549,27923,27924,45994</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1333916$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10785559$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bertelli, Lucia</creatorcontrib><creatorcontrib>Biagi, Giuliana</creatorcontrib><creatorcontrib>Giorgi, Irene</creatorcontrib><creatorcontrib>Livi, Oreste</creatorcontrib><creatorcontrib>Manera, Clementina</creatorcontrib><creatorcontrib>Scartoni, Valerio</creatorcontrib><creatorcontrib>Lucacchini, Antonio</creatorcontrib><creatorcontrib>Giannaccini, Gino</creatorcontrib><creatorcontrib>Barili, Pier Luigi</creatorcontrib><title>Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>This paper reports the synthesis and evaluation of the biological affinity towards benzodiazepine and A
1 and A
2A adenosine receptors of some 3-ethoxycarbonyl or 3-phenyl-substituted 1,2,3-triazolo[1,5-a]quinazolines. Starting from the appropriate chloro-substituted phenylazides, the series of 7 or 8 chloro-substituted triazoloquinazolines were prepared. Nitration reactions of the triazoloquinazoline ring and chlorination reactions of the hydroxyl group in the 5 position of the same ring are also reported. By nucleophilic displacement of halogen, the corresponding 5-amino derivatives and some analogous derivatives bearing cyclohexylamino and
p-toluidino substituents were obtained. The binding assays showed a generalized decrease in the affinity towards the benzodiazepine receptors and confirmed a moderate affinity towards the A
1 adenosine receptors in comparison with the previously studied triazoloquinazoline derivatives.</description><subject>1,2,3-triazoles</subject><subject>1,2,3-triazolo[1,5-a]quinazolines</subject><subject>A 1 and A 2A adenosine receptor binding</subject><subject>Animals</subject><subject>benzodiazepine receptor binding</subject><subject>Binding, Competitive - drug effects</subject><subject>Biological and medical sciences</subject><subject>Cattle</subject><subject>Chemical Phenomena</subject><subject>Chemistry, Physical</subject><subject>Gabaergic and benzodiazepinic system</subject><subject>In Vitro Techniques</subject><subject>Ligands</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Neostriatum - drug effects</subject><subject>Neostriatum - metabolism</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinazolines - chemical synthesis</subject><subject>Quinazolines - pharmacology</subject><subject>Receptor, Adenosine A2A</subject><subject>Receptors, GABA-A - drug effects</subject><subject>Receptors, Purinergic P1 - drug effects</subject><subject>Structure-Activity Relationship</subject><subject>Triazoles - chemical synthesis</subject><subject>Triazoles - pharmacology</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1rFTEUhoMo9rb6E5RZiCjc0ZOvuZluRIq1hYKLdicSMskZjcxNbpNMof31zf1A3bk6vJznzcdDyCsKHyjQ7uM1MMZbybh4B_C-BypFK5-QBV11quVMiqdk8Qc5Isc5_wYA2QE8J0cUVkpK2S9IuJ6HXHyZC7qGLtmStyV58xCn-J0uZWt-3M4-bLMPmE-bfB_KL8w-Nya4ZvDB-fCzKbEZMDxEV5u4qeRuaxyGmLcpocVNiSm_IM9GM2V8eZgn5Ob8y83ZRXv17evl2eer1grZlZaDGASMzo1G9UqgtZyOxrJhlIz2jHcKBuiEYOh6FGrErqu_tMPKGFRu4Cfk7f7YTYq3M-ai1z5bnCYTMM5ZrygoTrmqoNyDNsWcE456k_zapHtNQW89651nvZWoAfTOs5a19_pwwTys0f3T2outwJsDYLI105hMsD7_5TjnPe0q9mmPYZVx5zHpbD0Gi85XZ0W76P_zkkfyKpsl</recordid><startdate>20000301</startdate><enddate>20000301</enddate><creator>Bertelli, Lucia</creator><creator>Biagi, Giuliana</creator><creator>Giorgi, Irene</creator><creator>Livi, Oreste</creator><creator>Manera, Clementina</creator><creator>Scartoni, Valerio</creator><creator>Lucacchini, Antonio</creator><creator>Giannaccini, Gino</creator><creator>Barili, Pier Luigi</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>20000301</creationdate><title>Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors</title><author>Bertelli, Lucia ; Biagi, Giuliana ; Giorgi, Irene ; Livi, Oreste ; Manera, Clementina ; Scartoni, Valerio ; Lucacchini, Antonio ; Giannaccini, Gino ; Barili, Pier Luigi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c456t-304b40fddfa8984ecc31fac2bf521923680b06442ed9e48fe66234cb7aae8db3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>1,2,3-triazoles</topic><topic>1,2,3-triazolo[1,5-a]quinazolines</topic><topic>A 1 and A 2A adenosine receptor binding</topic><topic>Animals</topic><topic>benzodiazepine receptor binding</topic><topic>Binding, Competitive - drug effects</topic><topic>Biological and medical sciences</topic><topic>Cattle</topic><topic>Chemical Phenomena</topic><topic>Chemistry, Physical</topic><topic>Gabaergic and benzodiazepinic system</topic><topic>In Vitro Techniques</topic><topic>Ligands</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Neostriatum - drug effects</topic><topic>Neostriatum - metabolism</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinazolines - chemical synthesis</topic><topic>Quinazolines - pharmacology</topic><topic>Receptor, Adenosine A2A</topic><topic>Receptors, GABA-A - drug effects</topic><topic>Receptors, Purinergic P1 - drug effects</topic><topic>Structure-Activity Relationship</topic><topic>Triazoles - chemical synthesis</topic><topic>Triazoles - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bertelli, Lucia</creatorcontrib><creatorcontrib>Biagi, Giuliana</creatorcontrib><creatorcontrib>Giorgi, Irene</creatorcontrib><creatorcontrib>Livi, Oreste</creatorcontrib><creatorcontrib>Manera, Clementina</creatorcontrib><creatorcontrib>Scartoni, Valerio</creatorcontrib><creatorcontrib>Lucacchini, Antonio</creatorcontrib><creatorcontrib>Giannaccini, Gino</creatorcontrib><creatorcontrib>Barili, Pier Luigi</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>Bertelli, Lucia</au><au>Biagi, Giuliana</au><au>Giorgi, Irene</au><au>Livi, Oreste</au><au>Manera, Clementina</au><au>Scartoni, Valerio</au><au>Lucacchini, Antonio</au><au>Giannaccini, Gino</au><au>Barili, Pier Luigi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2000-03-01</date><risdate>2000</risdate><volume>35</volume><issue>3</issue><spage>333</spage><epage>341</epage><pages>333-341</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>This paper reports the synthesis and evaluation of the biological affinity towards benzodiazepine and A
1 and A
2A adenosine receptors of some 3-ethoxycarbonyl or 3-phenyl-substituted 1,2,3-triazolo[1,5-a]quinazolines. Starting from the appropriate chloro-substituted phenylazides, the series of 7 or 8 chloro-substituted triazoloquinazolines were prepared. Nitration reactions of the triazoloquinazoline ring and chlorination reactions of the hydroxyl group in the 5 position of the same ring are also reported. By nucleophilic displacement of halogen, the corresponding 5-amino derivatives and some analogous derivatives bearing cyclohexylamino and
p-toluidino substituents were obtained. The binding assays showed a generalized decrease in the affinity towards the benzodiazepine receptors and confirmed a moderate affinity towards the A
1 adenosine receptors in comparison with the previously studied triazoloquinazoline derivatives.</abstract><cop>Oxford</cop><pub>Elsevier Masson SAS</pub><pmid>10785559</pmid><doi>10.1016/S0223-5234(00)90154-5</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0223-5234 |
| ispartof | European journal of medicinal chemistry, 2000-03, Vol.35 (3), p.333-341 |
| issn | 0223-5234 1768-3254 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_71083138 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | 1,2,3-triazoles 1,2,3-triazolo[1,5-a]quinazolines A 1 and A 2A adenosine receptor binding Animals benzodiazepine receptor binding Binding, Competitive - drug effects Biological and medical sciences Cattle Chemical Phenomena Chemistry, Physical Gabaergic and benzodiazepinic system In Vitro Techniques Ligands Magnetic Resonance Spectroscopy Medical sciences Neostriatum - drug effects Neostriatum - metabolism Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology. Drug treatments Quinazolines - chemical synthesis Quinazolines - pharmacology Receptor, Adenosine A2A Receptors, GABA-A - drug effects Receptors, Purinergic P1 - drug effects Structure-Activity Relationship Triazoles - chemical synthesis Triazoles - pharmacology |
| title | Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-08T14%3A51%3A43IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Substituted%201,2,3-triazolo%5B1,5-a%5Dquinazolines:%20synthesis%20and%20binding%20to%20benzodiazepine%20and%20adenosine%20receptors&rft.jtitle=European%20journal%20of%20medicinal%20chemistry&rft.au=Bertelli,%20Lucia&rft.date=2000-03-01&rft.volume=35&rft.issue=3&rft.spage=333&rft.epage=341&rft.pages=333-341&rft.issn=0223-5234&rft.eissn=1768-3254&rft.coden=EJMCA5&rft_id=info:doi/10.1016/S0223-5234(00)90154-5&rft_dat=%3Cproquest_cross%3E71083138%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=71083138&rft_id=info:pmid/10785559&rft_els_id=S0223523400901545&rfr_iscdi=true |