Tricyclic ureas: A new class of HIV-1 protease inhibitors
A new class of tricyclic ureas containing a conformationally constrained proline was designed with the aid of molecular modeling. Efficient stereoselective intermolecular pinacol coupling represented the highlight of the synthesis. These rigid cyclic ureas are active towards HIV-1 protease, with 9 b...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 1998-12, Vol.8 (24), p.3615-3620 |
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| container_issue | 24 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Han, Wei Pelletier, Jeffrey C. Hodge, C.Nicholas |
| description | A new class of tricyclic ureas containing a conformationally constrained proline was designed with the aid of molecular modeling. Efficient stereoselective intermolecular pinacol coupling represented the highlight of the synthesis. These rigid cyclic ureas are active towards HIV-1 protease, with
9 being the most potent compound (Ki = 9 nM) despite interacting with only three side chain binding pockets of HIV protease.
A new class of tricyclic ureas containing a conformationally constrained proline was designed and synthesized. These rigid cyclic ureas are active towards HIV-1 protease, with
9 being the most potent compound (Ki = 9 nM) despite interacting with only three side chain binding pockets of HIV protease. |
| doi_str_mv | 10.1016/S0960-894X(98)00659-3 |
| format | Article |
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9 being the most potent compound (Ki = 9 nM) despite interacting with only three side chain binding pockets of HIV protease.
A new class of tricyclic ureas containing a conformationally constrained proline was designed and synthesized. These rigid cyclic ureas are active towards HIV-1 protease, with
9 being the most potent compound (Ki = 9 nM) despite interacting with only three side chain binding pockets of HIV protease.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(98)00659-3</identifier><identifier>PMID: 9934481</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>AIDS/HIV ; Anti-HIV Agents - chemistry ; Anti-HIV Agents - pharmacology ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Biological and medical sciences ; HIV Protease Inhibitors - chemistry ; HIV Protease Inhibitors - pharmacology ; HIV-1 - drug effects ; Medical sciences ; Molecular Structure ; Pharmacology. Drug treatments ; Urea - analogs & derivatives ; Urea - chemistry ; Urea - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry letters, 1998-12, Vol.8 (24), p.3615-3620</ispartof><rights>1998</rights><rights>1999 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c387t-39548e2ac4d3a756727dc5aa8cd0faef3e47297d495a27af85323ebb0e1dae1d3</citedby><cites>FETCH-LOGICAL-c387t-39548e2ac4d3a756727dc5aa8cd0faef3e47297d495a27af85323ebb0e1dae1d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0960-894X(98)00659-3$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1661664$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9934481$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Han, Wei</creatorcontrib><creatorcontrib>Pelletier, Jeffrey C.</creatorcontrib><creatorcontrib>Hodge, C.Nicholas</creatorcontrib><title>Tricyclic ureas: A new class of HIV-1 protease inhibitors</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A new class of tricyclic ureas containing a conformationally constrained proline was designed with the aid of molecular modeling. Efficient stereoselective intermolecular pinacol coupling represented the highlight of the synthesis. These rigid cyclic ureas are active towards HIV-1 protease, with
9 being the most potent compound (Ki = 9 nM) despite interacting with only three side chain binding pockets of HIV protease.
A new class of tricyclic ureas containing a conformationally constrained proline was designed and synthesized. These rigid cyclic ureas are active towards HIV-1 protease, with
9 being the most potent compound (Ki = 9 nM) despite interacting with only three side chain binding pockets of HIV protease.</description><subject>AIDS/HIV</subject><subject>Anti-HIV Agents - chemistry</subject><subject>Anti-HIV Agents - pharmacology</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral agents</subject><subject>Biological and medical sciences</subject><subject>HIV Protease Inhibitors - chemistry</subject><subject>HIV Protease Inhibitors - pharmacology</subject><subject>HIV-1 - drug effects</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Urea - analogs & derivatives</subject><subject>Urea - chemistry</subject><subject>Urea - pharmacology</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM9LwzAUx4Moc07_hEEPInqoJs2PJl5kDHXCwINTvIU0fcVI186kVfbf221lHoUX3uH7eS-PD0Jjgq8JJuLmBSuBY6nY-6WSVxgLrmJ6gIaECRZThvkhGu6RY3QSwifGhGHGBmigFGVMkiFSC-_s2pbORq0HE26jSVTBT2RLE0JUF9Hs6S0m0crXTZdC5KoPl7mm9uEUHRWmDHDW9xF6fbhfTGfx_PnxaTqZx5bKtImp4kxCYizLqUm5SJM0t9wYaXNcGCgosDRRac4UN0lqCslpQiHLMJDcdI-O0MVub3fDVwuh0UsXLJSlqaBugxaKCEY57UC-A62vQ_BQ6JV3S-PXmmC9Uaa3yvTGh1ZSb5Xpzdy4_6DNlpDvp3pHXX7e5yZYUxbeVNaFv-VCdMU67G6HQSfj24HXwTqoLOTOg210Xrt_DvkFzSqHaQ</recordid><startdate>19981215</startdate><enddate>19981215</enddate><creator>Han, Wei</creator><creator>Pelletier, Jeffrey C.</creator><creator>Hodge, C.Nicholas</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>7X8</scope></search><sort><creationdate>19981215</creationdate><title>Tricyclic ureas: A new class of HIV-1 protease inhibitors</title><author>Han, Wei ; Pelletier, Jeffrey C. ; Hodge, C.Nicholas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c387t-39548e2ac4d3a756727dc5aa8cd0faef3e47297d495a27af85323ebb0e1dae1d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>AIDS/HIV</topic><topic>Anti-HIV Agents - chemistry</topic><topic>Anti-HIV Agents - pharmacology</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiviral agents</topic><topic>Biological and medical sciences</topic><topic>HIV Protease Inhibitors - chemistry</topic><topic>HIV Protease Inhibitors - pharmacology</topic><topic>HIV-1 - drug effects</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Urea - analogs & derivatives</topic><topic>Urea - chemistry</topic><topic>Urea - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Han, Wei</creatorcontrib><creatorcontrib>Pelletier, Jeffrey C.</creatorcontrib><creatorcontrib>Hodge, C.Nicholas</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Han, Wei</au><au>Pelletier, Jeffrey C.</au><au>Hodge, C.Nicholas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tricyclic ureas: A new class of HIV-1 protease inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>1998-12-15</date><risdate>1998</risdate><volume>8</volume><issue>24</issue><spage>3615</spage><epage>3620</epage><pages>3615-3620</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A new class of tricyclic ureas containing a conformationally constrained proline was designed with the aid of molecular modeling. Efficient stereoselective intermolecular pinacol coupling represented the highlight of the synthesis. These rigid cyclic ureas are active towards HIV-1 protease, with
9 being the most potent compound (Ki = 9 nM) despite interacting with only three side chain binding pockets of HIV protease.
A new class of tricyclic ureas containing a conformationally constrained proline was designed and synthesized. These rigid cyclic ureas are active towards HIV-1 protease, with
9 being the most potent compound (Ki = 9 nM) despite interacting with only three side chain binding pockets of HIV protease.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>9934481</pmid><doi>10.1016/S0960-894X(98)00659-3</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 1998-12, Vol.8 (24), p.3615-3620 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_69164353 |
| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | AIDS/HIV Anti-HIV Agents - chemistry Anti-HIV Agents - pharmacology Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Biological and medical sciences HIV Protease Inhibitors - chemistry HIV Protease Inhibitors - pharmacology HIV-1 - drug effects Medical sciences Molecular Structure Pharmacology. Drug treatments Urea - analogs & derivatives Urea - chemistry Urea - pharmacology |
| title | Tricyclic ureas: A new class of HIV-1 protease inhibitors |
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