Intermolecular interactions in the crystal structures of potential HIV-1 integrase inhibitors
2-[(2,5-dichloro-4-nitro-phenylamino)-methoxy-methyl]-8-hydroxy-quinoline 1 and 2-methyl-quinoline-5,8-dione-5-oxime 2 were obtained as potential HIV-1 integrase inhibitors. They were synthesized and analyzed by X-ray crystallography. Semiempirical theoretical calculations of energy preferred confor...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2006-02, Vol.16 (4), p.1005-1009 |
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| creator | Majerz-Maniecka, Katarzyna Musiol, Robert Nitek, Wojciech Oleksyn, Barbara J. Mouscadet, Jean-Francois Bret, Marc Le Polanski, Jaroslaw |
| description | 2-[(2,5-dichloro-4-nitro-phenylamino)-methoxy-methyl]-8-hydroxy-quinoline
1 and 2-methyl-quinoline-5,8-dione-5-oxime
2 were obtained as potential HIV-1 integrase inhibitors. They were synthesized and analyzed by X-ray crystallography. Semiempirical theoretical calculations of energy preferred conformations were also carried out. The crystal structures of both compounds are stabilized via hydrogen bonds and π–π stacking interactions. The planarity of compound
1 is caused by intramolecular hydrogen bonds.
2-[(2,5-dichloro-4-nitro-phenylamino)-methoxy-methyl]-8-hydroxy-quinoline
1 and 2-methyl-quinoline-5,8-dione-5-oxime
2 were obtained as potential HIV-1 integrase inhibitors and analyzed by X-ray crystallography. Semiempirical theoretical calculations of energy preferred conformations were also carried out. The crystal structures of both compounds are stabilized via hydrogen bonds and π–π stacking interactions. The planarity of compound
1 is caused by intramolecular hydrogen bonds. |
| doi_str_mv | 10.1016/j.bmcl.2005.10.083 |
| format | Article |
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1 and 2-methyl-quinoline-5,8-dione-5-oxime
2 were obtained as potential HIV-1 integrase inhibitors. They were synthesized and analyzed by X-ray crystallography. Semiempirical theoretical calculations of energy preferred conformations were also carried out. The crystal structures of both compounds are stabilized via hydrogen bonds and π–π stacking interactions. The planarity of compound
1 is caused by intramolecular hydrogen bonds.
2-[(2,5-dichloro-4-nitro-phenylamino)-methoxy-methyl]-8-hydroxy-quinoline
1 and 2-methyl-quinoline-5,8-dione-5-oxime
2 were obtained as potential HIV-1 integrase inhibitors and analyzed by X-ray crystallography. Semiempirical theoretical calculations of energy preferred conformations were also carried out. The crystal structures of both compounds are stabilized via hydrogen bonds and π–π stacking interactions. The planarity of compound
1 is caused by intramolecular hydrogen bonds.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2005.10.083</identifier><identifier>PMID: 16289813</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Biological and medical sciences ; Crystal structure ; Crystallization ; Crystallography, X-Ray ; HIV Integrase - drug effects ; HIV Integrase Inhibitors - chemistry ; HIV Integrase Inhibitors - pharmacology ; HIV-1 integrase inhibitor ; Human immunodeficiency virus 1 ; Medical sciences ; Models, Molecular ; Molecular Structure ; Pharmacology. Drug treatments ; Quinoline ; Quinolines - chemistry ; Quinolines - pharmacology ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2006-02, Vol.16 (4), p.1005-1009</ispartof><rights>2005 Elsevier Ltd</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-f9b17f7db7d450d3b6662a980f6a26f3350eee8eaefacf33a02c84ca921c123d3</citedby><cites>FETCH-LOGICAL-c415t-f9b17f7db7d450d3b6662a980f6a26f3350eee8eaefacf33a02c84ca921c123d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2005.10.083$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27928,27929,45999</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17557090$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16289813$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Majerz-Maniecka, Katarzyna</creatorcontrib><creatorcontrib>Musiol, Robert</creatorcontrib><creatorcontrib>Nitek, Wojciech</creatorcontrib><creatorcontrib>Oleksyn, Barbara J.</creatorcontrib><creatorcontrib>Mouscadet, Jean-Francois</creatorcontrib><creatorcontrib>Bret, Marc Le</creatorcontrib><creatorcontrib>Polanski, Jaroslaw</creatorcontrib><title>Intermolecular interactions in the crystal structures of potential HIV-1 integrase inhibitors</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>2-[(2,5-dichloro-4-nitro-phenylamino)-methoxy-methyl]-8-hydroxy-quinoline
1 and 2-methyl-quinoline-5,8-dione-5-oxime
2 were obtained as potential HIV-1 integrase inhibitors. They were synthesized and analyzed by X-ray crystallography. Semiempirical theoretical calculations of energy preferred conformations were also carried out. The crystal structures of both compounds are stabilized via hydrogen bonds and π–π stacking interactions. The planarity of compound
1 is caused by intramolecular hydrogen bonds.
2-[(2,5-dichloro-4-nitro-phenylamino)-methoxy-methyl]-8-hydroxy-quinoline
1 and 2-methyl-quinoline-5,8-dione-5-oxime
2 were obtained as potential HIV-1 integrase inhibitors and analyzed by X-ray crystallography. Semiempirical theoretical calculations of energy preferred conformations were also carried out. The crystal structures of both compounds are stabilized via hydrogen bonds and π–π stacking interactions. The planarity of compound
1 is caused by intramolecular hydrogen bonds.</description><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral agents</subject><subject>Biological and medical sciences</subject><subject>Crystal structure</subject><subject>Crystallization</subject><subject>Crystallography, X-Ray</subject><subject>HIV Integrase - drug effects</subject><subject>HIV Integrase Inhibitors - chemistry</subject><subject>HIV Integrase Inhibitors - pharmacology</subject><subject>HIV-1 integrase inhibitor</subject><subject>Human immunodeficiency virus 1</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinoline</subject><subject>Quinolines - chemistry</subject><subject>Quinolines - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v1DAQhi1ERbeFP8AB5QK3bMefSSQuqIJ2pUpcCuKCLMcZU6-SeLEdpP77OuxKvcHJnlfPOxo9hLylsKVA1dV-20923DIAWYIttPwF2VChRM0FyJdkA52Cuu3Ej3NykdIegAoQ4hU5p4q1XUv5hvzczRnjFEa0y2hi5dfR2OzDnMpQ5QesbHxM2YxVynGxeYmYquCqQ8g4Z1_y2933mv5t_oomYfk9-N7nENNrcubMmPDN6b0k3758vr--re--3uyuP93VVlCZa9f1tHHN0DeDkDDwXinFTNeCU4Ypx7kERGzRoDO2jAaYbYU1HaOWMj7wS_LhuPcQw-8FU9aTTxbH0cwYlqRVo6hqoPsvSBshGaeygOwI2hhSiuj0IfrJxEdNQa_29V6v9vVqf82K_VJ6d9q-9BMOz5WT7gK8PwEmWTO6aGbr0zPXSFmuhMJ9PHJYpP3xGHWyHmeLg49osx6C_9cdT60ZpJo</recordid><startdate>20060215</startdate><enddate>20060215</enddate><creator>Majerz-Maniecka, Katarzyna</creator><creator>Musiol, Robert</creator><creator>Nitek, Wojciech</creator><creator>Oleksyn, Barbara J.</creator><creator>Mouscadet, Jean-Francois</creator><creator>Bret, Marc Le</creator><creator>Polanski, Jaroslaw</creator><general>Elsevier Ltd</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>7QO</scope><scope>7U9</scope><scope>8FD</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20060215</creationdate><title>Intermolecular interactions in the crystal structures of potential HIV-1 integrase inhibitors</title><author>Majerz-Maniecka, Katarzyna ; Musiol, Robert ; Nitek, Wojciech ; Oleksyn, Barbara J. ; Mouscadet, Jean-Francois ; Bret, Marc Le ; Polanski, Jaroslaw</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-f9b17f7db7d450d3b6662a980f6a26f3350eee8eaefacf33a02c84ca921c123d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiviral agents</topic><topic>Biological and medical sciences</topic><topic>Crystal structure</topic><topic>Crystallization</topic><topic>Crystallography, X-Ray</topic><topic>HIV Integrase - drug effects</topic><topic>HIV Integrase Inhibitors - chemistry</topic><topic>HIV Integrase Inhibitors - pharmacology</topic><topic>HIV-1 integrase inhibitor</topic><topic>Human immunodeficiency virus 1</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinoline</topic><topic>Quinolines - chemistry</topic><topic>Quinolines - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Majerz-Maniecka, Katarzyna</creatorcontrib><creatorcontrib>Musiol, Robert</creatorcontrib><creatorcontrib>Nitek, Wojciech</creatorcontrib><creatorcontrib>Oleksyn, Barbara J.</creatorcontrib><creatorcontrib>Mouscadet, Jean-Francois</creatorcontrib><creatorcontrib>Bret, Marc Le</creatorcontrib><creatorcontrib>Polanski, Jaroslaw</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>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Majerz-Maniecka, Katarzyna</au><au>Musiol, Robert</au><au>Nitek, Wojciech</au><au>Oleksyn, Barbara J.</au><au>Mouscadet, Jean-Francois</au><au>Bret, Marc Le</au><au>Polanski, Jaroslaw</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Intermolecular interactions in the crystal structures of potential HIV-1 integrase inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2006-02-15</date><risdate>2006</risdate><volume>16</volume><issue>4</issue><spage>1005</spage><epage>1009</epage><pages>1005-1009</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>2-[(2,5-dichloro-4-nitro-phenylamino)-methoxy-methyl]-8-hydroxy-quinoline
1 and 2-methyl-quinoline-5,8-dione-5-oxime
2 were obtained as potential HIV-1 integrase inhibitors. They were synthesized and analyzed by X-ray crystallography. Semiempirical theoretical calculations of energy preferred conformations were also carried out. The crystal structures of both compounds are stabilized via hydrogen bonds and π–π stacking interactions. The planarity of compound
1 is caused by intramolecular hydrogen bonds.
2-[(2,5-dichloro-4-nitro-phenylamino)-methoxy-methyl]-8-hydroxy-quinoline
1 and 2-methyl-quinoline-5,8-dione-5-oxime
2 were obtained as potential HIV-1 integrase inhibitors and analyzed by X-ray crystallography. Semiempirical theoretical calculations of energy preferred conformations were also carried out. The crystal structures of both compounds are stabilized via hydrogen bonds and π–π stacking interactions. The planarity of compound
1 is caused by intramolecular hydrogen bonds.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16289813</pmid><doi>10.1016/j.bmcl.2005.10.083</doi><tpages>5</tpages></addata></record> |
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| subjects | Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Biological and medical sciences Crystal structure Crystallization Crystallography, X-Ray HIV Integrase - drug effects HIV Integrase Inhibitors - chemistry HIV Integrase Inhibitors - pharmacology HIV-1 integrase inhibitor Human immunodeficiency virus 1 Medical sciences Models, Molecular Molecular Structure Pharmacology. Drug treatments Quinoline Quinolines - chemistry Quinolines - pharmacology Structure-Activity Relationship |
| title | Intermolecular interactions in the crystal structures of potential HIV-1 integrase inhibitors |
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