Synthesis and pharmacological evaluation of (2-oxaadamant-1-yl)amines
Several (2-oxaadamant-1-yl)amines have been synthesized and their antiviral, NMDA receptor antagonist, and trypanocidal activities have been studied. The synthesis of several (2-oxaadamant-1-yl)amines is reported. They were evaluated as NMDA receptor antagonists and several of them were more active...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2009-04, Vol.17 (8), p.3198-3206 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Duque, María D. Camps, Pelayo Profire, Lenuta Montaner, Silvia Vázquez, Santiago Sureda, Francesc X. Mallol, Jordi López-Querol, Marta Naesens, Lieve Clercq, Erik De Radhika Prathalingam, S. Kelly, John M. |
| description | Several (2-oxaadamant-1-yl)amines have been synthesized and their antiviral, NMDA receptor antagonist, and trypanocidal activities have been studied.
The synthesis of several (2-oxaadamant-1-yl)amines is reported. They were evaluated as NMDA receptor antagonists and several of them were more active than amantadine, but none was more potent than memantine. None of the tested compounds displayed antiviral activity. Two of the derivatives showed a significant level of trypanocidal activity. |
| doi_str_mv | 10.1016/j.bmc.2009.02.007 |
| format | Article |
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The synthesis of several (2-oxaadamant-1-yl)amines is reported. They were evaluated as NMDA receptor antagonists and several of them were more active than amantadine, but none was more potent than memantine. None of the tested compounds displayed antiviral activity. Two of the derivatives showed a significant level of trypanocidal activity.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2009.02.007</identifier><identifier>PMID: 19251424</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Adamantane ; Adamantane - analogs & derivatives ; Adamantane - chemical synthesis ; Adamantane - pharmacology ; Amantadine ; Amines - chemical synthesis ; Amines - pharmacology ; Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiparasitic agents ; Antiviral Agents - chemical synthesis ; Antiviral Agents - pharmacology ; Biological and medical sciences ; Cage compounds ; Cell Culture Techniques ; Glutamatergic system (aspartate and other excitatory aminoacids) ; Medical sciences ; Memantine ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; NGP1-01 ; NMDA ; Pharmacology. Drug treatments ; Receptors, N-Methyl-D-Aspartate - antagonists & inhibitors ; Receptors, N-Methyl-D-Aspartate - metabolism ; Trypanocidal Agents - chemical synthesis ; Trypanocidal Agents - pharmacology ; Trypanosoma</subject><ispartof>Bioorganic & medicinal chemistry, 2009-04, Vol.17 (8), p.3198-3206</ispartof><rights>2009 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><rights>Copyright © 2009 Elsevier Ltd. Published by Elsevier Ltd. All rights reserved. 2009 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c511t-8819e3efae92423d79c09d4253078f9457b5de2653b8f952ca14bf479e56d47e3</citedby><cites>FETCH-LOGICAL-c511t-8819e3efae92423d79c09d4253078f9457b5de2653b8f952ca14bf479e56d47e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2009.02.007$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21391739$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19251424$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Duque, María D.</creatorcontrib><creatorcontrib>Camps, Pelayo</creatorcontrib><creatorcontrib>Profire, Lenuta</creatorcontrib><creatorcontrib>Montaner, Silvia</creatorcontrib><creatorcontrib>Vázquez, Santiago</creatorcontrib><creatorcontrib>Sureda, Francesc X.</creatorcontrib><creatorcontrib>Mallol, Jordi</creatorcontrib><creatorcontrib>López-Querol, Marta</creatorcontrib><creatorcontrib>Naesens, Lieve</creatorcontrib><creatorcontrib>Clercq, Erik De</creatorcontrib><creatorcontrib>Radhika Prathalingam, S.</creatorcontrib><creatorcontrib>Kelly, John M.</creatorcontrib><title>Synthesis and pharmacological evaluation of (2-oxaadamant-1-yl)amines</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Several (2-oxaadamant-1-yl)amines have been synthesized and their antiviral, NMDA receptor antagonist, and trypanocidal activities have been studied.
The synthesis of several (2-oxaadamant-1-yl)amines is reported. They were evaluated as NMDA receptor antagonists and several of them were more active than amantadine, but none was more potent than memantine. None of the tested compounds displayed antiviral activity. Two of the derivatives showed a significant level of trypanocidal activity.</description><subject>Adamantane</subject><subject>Adamantane - analogs & derivatives</subject><subject>Adamantane - chemical synthesis</subject><subject>Adamantane - pharmacology</subject><subject>Amantadine</subject><subject>Amines - chemical synthesis</subject><subject>Amines - pharmacology</subject><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiparasitic agents</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cage compounds</subject><subject>Cell Culture Techniques</subject><subject>Glutamatergic system (aspartate and other excitatory aminoacids)</subject><subject>Medical sciences</subject><subject>Memantine</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>NGP1-01</subject><subject>NMDA</subject><subject>Pharmacology. Drug treatments</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 - pharmacology</subject><subject>Trypanosoma</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kU2LFDEQhoMo7uzqD_AifdHVQ7f57O4gCLKsH7DgQT2H6qR6J0N3MiY9g_PvzTLDqpc9FaGeeqnUQ8gLRhtGWftu0wyzbTiluqG8obR7RFZMtrIWQrPHZEV129e01-0ZOc95QynlUrOn5IxprpjkckWuvx_CssbscwXBVds1pBlsnOKttzBVuIdpB4uPoYpj9YbX8TeAgxnCUrP6ML2F2QfMz8iTEaaMz0_1gvz8dP3j6kt98-3z16uPN7VVjC113zONAkdAzSUXrtOWaie5ErTrRy1VNyiHvFViKE_FLTA5jLLTqFonOxQX5MMxd7sbZnQWw5JgMtvkZ0gHE8Gb_zvBr81t3BvBWce5KAGXp4AUf-0wL2b22eI0QcC4y6YTQvC2Z7SQrx8kOVXlmEoWkB1Bm2LOCcf7dRg1d5rMxhRN5k6TodwUTWXm5b__-Dtx8lKAVycAcvEwJgjW53uOsyK4E7pw748clqvvPSaTrcdg0fmEdjEu-gfW-APQGq9y</recordid><startdate>20090415</startdate><enddate>20090415</enddate><creator>Duque, María D.</creator><creator>Camps, Pelayo</creator><creator>Profire, Lenuta</creator><creator>Montaner, Silvia</creator><creator>Vázquez, Santiago</creator><creator>Sureda, Francesc X.</creator><creator>Mallol, Jordi</creator><creator>López-Querol, Marta</creator><creator>Naesens, Lieve</creator><creator>Clercq, Erik De</creator><creator>Radhika Prathalingam, S.</creator><creator>Kelly, John M.</creator><general>Elsevier Ltd</general><general>Elsevier</general><general>Elsevier Ltd. Published by Elsevier Ltd</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>7QO</scope><scope>7T7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20090415</creationdate><title>Synthesis and pharmacological evaluation of (2-oxaadamant-1-yl)amines</title><author>Duque, María D. ; Camps, Pelayo ; Profire, Lenuta ; Montaner, Silvia ; Vázquez, Santiago ; Sureda, Francesc X. ; Mallol, Jordi ; López-Querol, Marta ; Naesens, Lieve ; Clercq, Erik De ; Radhika Prathalingam, S. ; Kelly, John M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c511t-8819e3efae92423d79c09d4253078f9457b5de2653b8f952ca14bf479e56d47e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Adamantane</topic><topic>Adamantane - analogs & derivatives</topic><topic>Adamantane - chemical synthesis</topic><topic>Adamantane - pharmacology</topic><topic>Amantadine</topic><topic>Amines - chemical synthesis</topic><topic>Amines - pharmacology</topic><topic>Animals</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiparasitic agents</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cage compounds</topic><topic>Cell Culture Techniques</topic><topic>Glutamatergic system (aspartate and other excitatory aminoacids)</topic><topic>Medical sciences</topic><topic>Memantine</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>NGP1-01</topic><topic>NMDA</topic><topic>Pharmacology. Drug treatments</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 - pharmacology</topic><topic>Trypanosoma</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Duque, María D.</creatorcontrib><creatorcontrib>Camps, Pelayo</creatorcontrib><creatorcontrib>Profire, Lenuta</creatorcontrib><creatorcontrib>Montaner, Silvia</creatorcontrib><creatorcontrib>Vázquez, Santiago</creatorcontrib><creatorcontrib>Sureda, Francesc X.</creatorcontrib><creatorcontrib>Mallol, Jordi</creatorcontrib><creatorcontrib>López-Querol, Marta</creatorcontrib><creatorcontrib>Naesens, Lieve</creatorcontrib><creatorcontrib>Clercq, Erik De</creatorcontrib><creatorcontrib>Radhika Prathalingam, S.</creatorcontrib><creatorcontrib>Kelly, John M.</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>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</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>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</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>Duque, María D.</au><au>Camps, Pelayo</au><au>Profire, Lenuta</au><au>Montaner, Silvia</au><au>Vázquez, Santiago</au><au>Sureda, Francesc X.</au><au>Mallol, Jordi</au><au>López-Querol, Marta</au><au>Naesens, Lieve</au><au>Clercq, Erik De</au><au>Radhika Prathalingam, S.</au><au>Kelly, John M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and pharmacological evaluation of (2-oxaadamant-1-yl)amines</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2009-04-15</date><risdate>2009</risdate><volume>17</volume><issue>8</issue><spage>3198</spage><epage>3206</epage><pages>3198-3206</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Several (2-oxaadamant-1-yl)amines have been synthesized and their antiviral, NMDA receptor antagonist, and trypanocidal activities have been studied.
The synthesis of several (2-oxaadamant-1-yl)amines is reported. They were evaluated as NMDA receptor antagonists and several of them were more active than amantadine, but none was more potent than memantine. None of the tested compounds displayed antiviral activity. Two of the derivatives showed a significant level of trypanocidal activity.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19251424</pmid><doi>10.1016/j.bmc.2009.02.007</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2009-04, Vol.17 (8), p.3198-3206 |
| issn | 0968-0896 1464-3391 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Adamantane Adamantane - analogs & derivatives Adamantane - chemical synthesis Adamantane - pharmacology Amantadine Amines - chemical synthesis Amines - pharmacology Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antiparasitic agents Antiviral Agents - chemical synthesis Antiviral Agents - pharmacology Biological and medical sciences Cage compounds Cell Culture Techniques Glutamatergic system (aspartate and other excitatory aminoacids) Medical sciences Memantine Neuropharmacology Neurotransmitters. Neurotransmission. Receptors NGP1-01 NMDA Pharmacology. Drug treatments Receptors, N-Methyl-D-Aspartate - antagonists & inhibitors Receptors, N-Methyl-D-Aspartate - metabolism Trypanocidal Agents - chemical synthesis Trypanocidal Agents - pharmacology Trypanosoma |
| title | Synthesis and pharmacological evaluation of (2-oxaadamant-1-yl)amines |
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