Synthesis of benzopolycyclic cage amines: NMDA receptor antagonist, trypanocidal and antiviral activities
The synthesis of several 6,7,8,9,10,11-hexahydro-9-methyl-5,7:9,11-dimethano-5H-benzocyclononen-7-amines is reported. Several of them display low micromolar NMDA receptor antagonist and/or trypanocidal activities. Two compounds are endowed with micromolar anti vesicular stomatitis virus activity, wh...
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Veröffentlicht in: | Bioorganic & medicinal chemistry 2012-01, Vol.20 (2), p.942-948 |
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creator | Torres, Eva Duque, María D. López-Querol, Marta Taylor, Martin C. Naesens, Lieve Ma, Chunlong Pinto, Lawrence H. Sureda, Francesc X. Kelly, John M. Vázquez, Santiago |
description | The synthesis of several 6,7,8,9,10,11-hexahydro-9-methyl-5,7:9,11-dimethano-5H-benzocyclononen-7-amines is reported. Several of them display low micromolar NMDA receptor antagonist and/or trypanocidal activities. Two compounds are endowed with micromolar anti vesicular stomatitis virus activity, while only one compound shows micromolar anti-influenza activity. The anti-influenza activity of this compound does not seem to be mediated by blocking of the M2 protein. |
doi_str_mv | 10.1016/j.bmc.2011.11.050 |
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Several of them display low micromolar NMDA receptor antagonist and/or trypanocidal activities. Two compounds are endowed with micromolar anti vesicular stomatitis virus activity, while only one compound shows micromolar anti-influenza activity. The anti-influenza activity of this compound does not seem to be mediated by blocking of the M2 protein.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2011.11.050</identifier><identifier>PMID: 22178660</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Amantadine ; amines ; Amines - chemical synthesis ; Amines - chemistry ; Amines - pharmacology ; antagonists ; Antiviral activity ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; antiviral properties ; Antivirals ; Cage compounds ; chemistry ; DNA Viruses - drug effects ; Glutamic acid receptors (ionotropic) ; Humans ; N-Methyl-D-aspartic acid receptors ; NMDA ; Receptors, N-Methyl-D-Aspartate - antagonists & inhibitors ; Receptors, N-Methyl-D-Aspartate - metabolism ; Trypanocidal Agents - chemical synthesis ; Trypanocidal Agents - chemistry ; Trypanocidal Agents - pharmacology ; Trypanosoma ; Trypanosoma brucei brucei - drug effects ; Vesicular stomatitis virus ; Vesiculovirus</subject><ispartof>Bioorganic & medicinal chemistry, 2012-01, Vol.20 (2), p.942-948</ispartof><rights>2011 Elsevier Ltd</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><rights>Copyright © 2011 Elsevier Ltd. Published by Elsevier Ltd. All rights reserved. 2011 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c506t-f37c041228a0c3a97f259f98c69ef751ec66d7d0135e53a38d46a1f2421d8dfc3</citedby><cites>FETCH-LOGICAL-c506t-f37c041228a0c3a97f259f98c69ef751ec66d7d0135e53a38d46a1f2421d8dfc3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0968089611009862$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,776,780,881,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22178660$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Torres, Eva</creatorcontrib><creatorcontrib>Duque, María D.</creatorcontrib><creatorcontrib>López-Querol, Marta</creatorcontrib><creatorcontrib>Taylor, Martin C.</creatorcontrib><creatorcontrib>Naesens, Lieve</creatorcontrib><creatorcontrib>Ma, Chunlong</creatorcontrib><creatorcontrib>Pinto, Lawrence H.</creatorcontrib><creatorcontrib>Sureda, Francesc X.</creatorcontrib><creatorcontrib>Kelly, John M.</creatorcontrib><creatorcontrib>Vázquez, Santiago</creatorcontrib><title>Synthesis of benzopolycyclic cage amines: NMDA receptor antagonist, trypanocidal and antiviral activities</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>The synthesis of several 6,7,8,9,10,11-hexahydro-9-methyl-5,7:9,11-dimethano-5H-benzocyclononen-7-amines is reported. Several of them display low micromolar NMDA receptor antagonist and/or trypanocidal activities. Two compounds are endowed with micromolar anti vesicular stomatitis virus activity, while only one compound shows micromolar anti-influenza activity. The anti-influenza activity of this compound does not seem to be mediated by blocking of the M2 protein.</description><subject>Amantadine</subject><subject>amines</subject><subject>Amines - chemical synthesis</subject><subject>Amines - chemistry</subject><subject>Amines - pharmacology</subject><subject>antagonists</subject><subject>Antiviral activity</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>antiviral properties</subject><subject>Antivirals</subject><subject>Cage compounds</subject><subject>chemistry</subject><subject>DNA Viruses - drug effects</subject><subject>Glutamic acid receptors (ionotropic)</subject><subject>Humans</subject><subject>N-Methyl-D-aspartic acid receptors</subject><subject>NMDA</subject><subject>Receptors, N-Methyl-D-Aspartate - antagonists & inhibitors</subject><subject>Receptors, N-Methyl-D-Aspartate - metabolism</subject><subject>Trypanocidal Agents - chemical synthesis</subject><subject>Trypanocidal Agents - chemistry</subject><subject>Trypanocidal Agents - pharmacology</subject><subject>Trypanosoma</subject><subject>Trypanosoma brucei brucei - drug effects</subject><subject>Vesicular stomatitis virus</subject><subject>Vesiculovirus</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUtv1DAUhS0EokPhB7CB7NiQwY_YSUBCqlpeUoFF6dry2NdTjxI72J6R0l-PoykVbEC6km3d7x4d34PQc4LXBBPxZrfejHpNMSHrUpjjB2hFGtHUjPXkIVrhXnQ17npxgp6ktMMY06Ynj9EJpaTthMAr5K5mn28guVQFW23A34YpDLOe9eB0pdUWKjU6D-lt9e3rxVkVQcOUQ6yUz2obvEv5dZXjPCkftDNqKA2zNN3BxeWll1t2kJ6iR1YNCZ7dnafo-uOHH-ef68vvn76cn13WmmORa8tajRtCaaewZqpvLeW97TsterAtJ6CFMK3BhHHgTLHONEIRSxtKTGesZqfo_VF32m9GMBp8LkbkFN2o4iyDcvLvjnc3chsOkjHOGOmKwKs7gRh-7iFlObqkYRiUh7BPsqeMlkVS9n-SCE5b3iwkOZI6hpQi2Hs_BMslS7mTJUu5ZClLlSzLzIs_P3I_8Tu8Arw8AlYFqbbRJXl9VRQ4LioYC1qId0cCysIPDqJM2oHXYFwJMksT3D8M_AIgx7p6</recordid><startdate>20120115</startdate><enddate>20120115</enddate><creator>Torres, Eva</creator><creator>Duque, María D.</creator><creator>López-Querol, Marta</creator><creator>Taylor, Martin C.</creator><creator>Naesens, Lieve</creator><creator>Ma, Chunlong</creator><creator>Pinto, Lawrence H.</creator><creator>Sureda, Francesc X.</creator><creator>Kelly, John M.</creator><creator>Vázquez, Santiago</creator><general>Elsevier Ltd</general><general>Elsevier Ltd. Published by 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><scope>7QO</scope><scope>7T7</scope><scope>7TK</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope><scope>5PM</scope></search><sort><creationdate>20120115</creationdate><title>Synthesis of benzopolycyclic cage amines: NMDA receptor antagonist, trypanocidal and antiviral activities</title><author>Torres, Eva ; Duque, María D. ; López-Querol, Marta ; Taylor, Martin C. ; Naesens, Lieve ; Ma, Chunlong ; Pinto, Lawrence H. ; Sureda, Francesc X. ; Kelly, John M. ; Vázquez, Santiago</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c506t-f37c041228a0c3a97f259f98c69ef751ec66d7d0135e53a38d46a1f2421d8dfc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Amantadine</topic><topic>amines</topic><topic>Amines - chemical synthesis</topic><topic>Amines - chemistry</topic><topic>Amines - pharmacology</topic><topic>antagonists</topic><topic>Antiviral activity</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>antiviral properties</topic><topic>Antivirals</topic><topic>Cage compounds</topic><topic>chemistry</topic><topic>DNA Viruses - drug effects</topic><topic>Glutamic acid receptors (ionotropic)</topic><topic>Humans</topic><topic>N-Methyl-D-aspartic acid receptors</topic><topic>NMDA</topic><topic>Receptors, N-Methyl-D-Aspartate - antagonists & inhibitors</topic><topic>Receptors, N-Methyl-D-Aspartate - metabolism</topic><topic>Trypanocidal Agents - chemical synthesis</topic><topic>Trypanocidal Agents - chemistry</topic><topic>Trypanocidal Agents - pharmacology</topic><topic>Trypanosoma</topic><topic>Trypanosoma brucei brucei - drug effects</topic><topic>Vesicular stomatitis virus</topic><topic>Vesiculovirus</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Torres, Eva</creatorcontrib><creatorcontrib>Duque, María D.</creatorcontrib><creatorcontrib>López-Querol, Marta</creatorcontrib><creatorcontrib>Taylor, Martin C.</creatorcontrib><creatorcontrib>Naesens, Lieve</creatorcontrib><creatorcontrib>Ma, Chunlong</creatorcontrib><creatorcontrib>Pinto, Lawrence H.</creatorcontrib><creatorcontrib>Sureda, Francesc X.</creatorcontrib><creatorcontrib>Kelly, John M.</creatorcontrib><creatorcontrib>Vázquez, Santiago</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><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Neurosciences Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Torres, Eva</au><au>Duque, María D.</au><au>López-Querol, Marta</au><au>Taylor, Martin C.</au><au>Naesens, Lieve</au><au>Ma, Chunlong</au><au>Pinto, Lawrence H.</au><au>Sureda, Francesc X.</au><au>Kelly, John M.</au><au>Vázquez, Santiago</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of benzopolycyclic cage amines: NMDA receptor antagonist, trypanocidal and antiviral activities</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2012-01-15</date><risdate>2012</risdate><volume>20</volume><issue>2</issue><spage>942</spage><epage>948</epage><pages>942-948</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>The synthesis of several 6,7,8,9,10,11-hexahydro-9-methyl-5,7:9,11-dimethano-5H-benzocyclononen-7-amines is reported. Several of them display low micromolar NMDA receptor antagonist and/or trypanocidal activities. Two compounds are endowed with micromolar anti vesicular stomatitis virus activity, while only one compound shows micromolar anti-influenza activity. The anti-influenza activity of this compound does not seem to be mediated by blocking of the M2 protein.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>22178660</pmid><doi>10.1016/j.bmc.2011.11.050</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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subjects | Amantadine amines Amines - chemical synthesis Amines - chemistry Amines - pharmacology antagonists Antiviral activity Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology antiviral properties Antivirals Cage compounds chemistry DNA Viruses - drug effects Glutamic acid receptors (ionotropic) Humans N-Methyl-D-aspartic acid receptors NMDA Receptors, N-Methyl-D-Aspartate - antagonists & inhibitors Receptors, N-Methyl-D-Aspartate - metabolism Trypanocidal Agents - chemical synthesis Trypanocidal Agents - chemistry Trypanocidal Agents - pharmacology Trypanosoma Trypanosoma brucei brucei - drug effects Vesicular stomatitis virus Vesiculovirus |
title | Synthesis of benzopolycyclic cage amines: NMDA receptor antagonist, trypanocidal and antiviral activities |
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