Stereoselective Synthesis of 4′-Selenonucleosides via Seleno-Michael Reaction as Potent Antiviral Agents
Based on the hypothesis that the bulky selenium atom, with 4p orbitals, can sterically hinder the approach of a cellular kinase to 5′-OH for phosphorylation, 4′-selenonucleosides with one-carbon homologation were designed and synthesized via a novel seleno-Michael reaction, with the stereoselectivit...
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| Veröffentlicht in: | Organic letters 2014-11, Vol.16 (21), p.5796-5799 |
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| container_issue | 21 |
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| container_title | Organic letters |
| container_volume | 16 |
| creator | Sahu, Pramod K Kim, Gyudong Yu, Jinha Ahn, Ji Yoon Song, Jayoung Choi, Yoojin Jin, Xing Kim, Jin-Hee Lee, Sang Kook Park, Sunghyouk Jeong, Lak Shin |
| description | Based on the hypothesis that the bulky selenium atom, with 4p orbitals, can sterically hinder the approach of a cellular kinase to 5′-OH for phosphorylation, 4′-selenonucleosides with one-carbon homologation were designed and synthesized via a novel seleno-Michael reaction, with the stereoselectivity controlled by steric effects. 5′-Homo-4′-selenonucleosides (n = 2) demonstrated potent antiherpes simplex virus (HSV-1) activity, indicating that the bulky selenium atom might play a key role in preventing phosphorylation by cellular kinases, resulting in no antiviral activity. |
| doi_str_mv | 10.1021/ol502899b |
| format | Article |
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Lett</addtitle><description>Based on the hypothesis that the bulky selenium atom, with 4p orbitals, can sterically hinder the approach of a cellular kinase to 5′-OH for phosphorylation, 4′-selenonucleosides with one-carbon homologation were designed and synthesized via a novel seleno-Michael reaction, with the stereoselectivity controlled by steric effects. 5′-Homo-4′-selenonucleosides (n = 2) demonstrated potent antiherpes simplex virus (HSV-1) activity, indicating that the bulky selenium atom might play a key role in preventing phosphorylation by cellular kinases, resulting in no antiviral activity.</description><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Dideoxynucleosides - chemical synthesis</subject><subject>Dideoxynucleosides - chemistry</subject><subject>Dideoxynucleosides - pharmacology</subject><subject>Herpesvirus 1, Human - chemistry</subject><subject>Herpesvirus 1, Human - drug effects</subject><subject>Molecular Structure</subject><subject>Nucleic Acid Conformation</subject><subject>Organoselenium Compounds - chemical synthesis</subject><subject>Organoselenium Compounds - chemistry</subject><subject>Organoselenium Compounds - pharmacology</subject><subject>Phosphorylation</subject><subject>Simplexvirus - drug effects</subject><subject>Stereoisomerism</subject><subject>Thymidine Kinase - chemistry</subject><subject>Thymidine Kinase - pharmacology</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1OwzAQhS0EoqWw4ALIGyRYBPwTJ_GyqviTikAU1pGTjGmq1C52Uqk7zsSROAlGKV2xmpk33zxpHkKnlFxRwui1bQRhmZTFHhpSwXiUEsH2d31CBujI-wUhNCjyEA2Y4DFJGBuixawFB9ZDA2VbrwHPNqadg689thrH359f0SzsjDVd2QSursDjda1wr0aPdTlX0OAXUOHeGqw8frYtmBaPTTCsnWrw-D3M_hgdaNV4ONnWEXq7vXmd3EfTp7uHyXgaKU5FG8lCUpKVOhEikRrKoqCKxKmsQOqUyoLRSldAGJeZAp1yoYAkWUYSqmJNKsFH6KL3XTn70YFv82XtS2gaZcB2PqfhcZJwGfOAXvZo6az3DnS-cvVSuU1OSf4bbb6LNrBnW9uuWEK1I_-yDMB5D6jS5wvbORO-_MfoBziigeg</recordid><startdate>20141107</startdate><enddate>20141107</enddate><creator>Sahu, Pramod K</creator><creator>Kim, Gyudong</creator><creator>Yu, Jinha</creator><creator>Ahn, Ji Yoon</creator><creator>Song, Jayoung</creator><creator>Choi, Yoojin</creator><creator>Jin, Xing</creator><creator>Kim, Jin-Hee</creator><creator>Lee, Sang Kook</creator><creator>Park, Sunghyouk</creator><creator>Jeong, Lak Shin</creator><general>American Chemical Society</general><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>20141107</creationdate><title>Stereoselective Synthesis of 4′-Selenonucleosides via Seleno-Michael Reaction as Potent Antiviral Agents</title><author>Sahu, Pramod K ; Kim, Gyudong ; Yu, Jinha ; Ahn, Ji Yoon ; Song, Jayoung ; Choi, Yoojin ; Jin, Xing ; Kim, Jin-Hee ; Lee, Sang Kook ; Park, Sunghyouk ; Jeong, Lak Shin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-9b9108cf65569fecbb1a0479de9f719b21dfde02398aef735ae0688061a4f0d53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Dideoxynucleosides - chemical synthesis</topic><topic>Dideoxynucleosides - chemistry</topic><topic>Dideoxynucleosides - pharmacology</topic><topic>Herpesvirus 1, Human - chemistry</topic><topic>Herpesvirus 1, Human - drug effects</topic><topic>Molecular Structure</topic><topic>Nucleic Acid Conformation</topic><topic>Organoselenium Compounds - chemical synthesis</topic><topic>Organoselenium Compounds - chemistry</topic><topic>Organoselenium Compounds - pharmacology</topic><topic>Phosphorylation</topic><topic>Simplexvirus - drug effects</topic><topic>Stereoisomerism</topic><topic>Thymidine Kinase - chemistry</topic><topic>Thymidine Kinase - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sahu, Pramod K</creatorcontrib><creatorcontrib>Kim, Gyudong</creatorcontrib><creatorcontrib>Yu, Jinha</creatorcontrib><creatorcontrib>Ahn, Ji Yoon</creatorcontrib><creatorcontrib>Song, Jayoung</creatorcontrib><creatorcontrib>Choi, Yoojin</creatorcontrib><creatorcontrib>Jin, Xing</creatorcontrib><creatorcontrib>Kim, Jin-Hee</creatorcontrib><creatorcontrib>Lee, Sang Kook</creatorcontrib><creatorcontrib>Park, Sunghyouk</creatorcontrib><creatorcontrib>Jeong, Lak Shin</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sahu, Pramod K</au><au>Kim, Gyudong</au><au>Yu, Jinha</au><au>Ahn, Ji Yoon</au><au>Song, Jayoung</au><au>Choi, Yoojin</au><au>Jin, Xing</au><au>Kim, Jin-Hee</au><au>Lee, Sang Kook</au><au>Park, Sunghyouk</au><au>Jeong, Lak Shin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereoselective Synthesis of 4′-Selenonucleosides via Seleno-Michael Reaction as Potent Antiviral Agents</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2014-11-07</date><risdate>2014</risdate><volume>16</volume><issue>21</issue><spage>5796</spage><epage>5799</epage><pages>5796-5799</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Based on the hypothesis that the bulky selenium atom, with 4p orbitals, can sterically hinder the approach of a cellular kinase to 5′-OH for phosphorylation, 4′-selenonucleosides with one-carbon homologation were designed and synthesized via a novel seleno-Michael reaction, with the stereoselectivity controlled by steric effects. 5′-Homo-4′-selenonucleosides (n = 2) demonstrated potent antiherpes simplex virus (HSV-1) activity, indicating that the bulky selenium atom might play a key role in preventing phosphorylation by cellular kinases, resulting in no antiviral activity.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25340622</pmid><doi>10.1021/ol502899b</doi><tpages>4</tpages></addata></record> |
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| source | ACS Publications; MEDLINE |
| subjects | Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Dideoxynucleosides - chemical synthesis Dideoxynucleosides - chemistry Dideoxynucleosides - pharmacology Herpesvirus 1, Human - chemistry Herpesvirus 1, Human - drug effects Molecular Structure Nucleic Acid Conformation Organoselenium Compounds - chemical synthesis Organoselenium Compounds - chemistry Organoselenium Compounds - pharmacology Phosphorylation Simplexvirus - drug effects Stereoisomerism Thymidine Kinase - chemistry Thymidine Kinase - pharmacology |
| title | Stereoselective Synthesis of 4′-Selenonucleosides via Seleno-Michael Reaction as Potent Antiviral Agents |
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