Synthesis of a carbocyclic sialic acid analogue for the inhibition of influenza virus neuraminidase
The influenza virus neuraminidase (NA) is essential for viral infection and offers a potential target for antiviral drug development. We prepared a carbocyclic sialic acid analogue, potentially able to inhibit NA. Its structure is an analogue of the transition-state of the reaction catalysed by NA....
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| Veröffentlicht in: | Carbohydrate research 2001-05, Vol.332 (1), p.23-31 |
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| creator | Bianco, Armandodoriano Brufani, Mario Manna, Fedele Melchioni, Cristiana |
| description | The influenza virus neuraminidase (NA) is essential for viral infection and offers a potential target for antiviral drug development. We prepared a carbocyclic sialic acid analogue, potentially able to inhibit NA. Its structure is an analogue of the transition-state of the reaction catalysed by NA. As starting material, quinic acid was selected owing to its ready availability and its stereochemical feature suitable for the target structure. The quinic acid was first converted in the shikimic acid; then two of the three hydroxyl functions of this product were selectively functionalised to obtain the target molecule (3
R,4
S,5
R)-4-acetamido-3-guanidino-5-hydroxycyclohex-1-ene-1-carboxylic acid.
A carbocyclic sialic acid analogue
17, potentially able to inhibit neuraminidase (NA), was prepared. Its structure in an analogue of the transition state of the reaction catalysed by NA. |
| doi_str_mv | 10.1016/S0008-6215(01)00079-9 |
| format | Article |
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R,4
S,5
R)-4-acetamido-3-guanidino-5-hydroxycyclohex-1-ene-1-carboxylic acid.
A carbocyclic sialic acid analogue
17, potentially able to inhibit neuraminidase (NA), was prepared. Its structure in an analogue of the transition state of the reaction catalysed by NA.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/S0008-6215(01)00079-9</identifier><identifier>PMID: 11403085</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>Acetamides - pharmacology ; Antiviral agents ; Antiviral Agents - chemical synthesis ; Enzyme Inhibitors - chemical synthesis ; Guanidines - pharmacology ; Neuraminidase - antagonists & inhibitors ; Orthomyxoviridae - enzymology ; Shikimic acid ; Sialic acid</subject><ispartof>Carbohydrate research, 2001-05, Vol.332 (1), p.23-31</ispartof><rights>2001 Elsevier Science Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c361t-5c18b2f7247d104b95c80b74ed9355ee9e0d2e2165d4d05508d0773375f01cf23</citedby><cites>FETCH-LOGICAL-c361t-5c18b2f7247d104b95c80b74ed9355ee9e0d2e2165d4d05508d0773375f01cf23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0008621501000799$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11403085$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bianco, Armandodoriano</creatorcontrib><creatorcontrib>Brufani, Mario</creatorcontrib><creatorcontrib>Manna, Fedele</creatorcontrib><creatorcontrib>Melchioni, Cristiana</creatorcontrib><title>Synthesis of a carbocyclic sialic acid analogue for the inhibition of influenza virus neuraminidase</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>The influenza virus neuraminidase (NA) is essential for viral infection and offers a potential target for antiviral drug development. We prepared a carbocyclic sialic acid analogue, potentially able to inhibit NA. Its structure is an analogue of the transition-state of the reaction catalysed by NA. As starting material, quinic acid was selected owing to its ready availability and its stereochemical feature suitable for the target structure. The quinic acid was first converted in the shikimic acid; then two of the three hydroxyl functions of this product were selectively functionalised to obtain the target molecule (3
R,4
S,5
R)-4-acetamido-3-guanidino-5-hydroxycyclohex-1-ene-1-carboxylic acid.
A carbocyclic sialic acid analogue
17, potentially able to inhibit neuraminidase (NA), was prepared. Its structure in an analogue of the transition state of the reaction catalysed by NA.</description><subject>Acetamides - pharmacology</subject><subject>Antiviral agents</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Guanidines - pharmacology</subject><subject>Neuraminidase - antagonists & inhibitors</subject><subject>Orthomyxoviridae - enzymology</subject><subject>Shikimic acid</subject><subject>Sialic acid</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1r3DAQhkVpaDZJf0KLTqU5OBlZlmWfSgjNByzksC3kJmRp3EzxSqlkBza_Pt7skh5zGl543hnmYeyLgDMBoj5fAUBT1KVQ30GczkG3RfuBLUSjZVGV9f1HtnhDDtlRzn_nCLWuP7FDISqQ0KgFc6tNGB8wU-ax55Y7m7roNm4gxzPZ7bCOPLfBDvHPhLyPic8FTuGBOhophm2RQj9MGJ4tf6I0ZR5wSnZNgbzNeMIOejtk_Lyfx-z31c9flzfF8u769vJiWThZi7FQTjRd2euy0l5A1bXKNdDpCn0rlUJsEXyJpaiVrzwoBY0HraXUqgfh-lIes2-7vY8p_pswj2ZN2eEw2IBxykZDK4VUzQyqHehSzDlhbx4TrW3aGAFma9e82jVbdQaEebVr2rn3dX9g6tbo_7f2Omfgxw7A-c0nwmSyIwwOPSV0o_GR3jnxAkSwigQ</recordid><startdate>20010508</startdate><enddate>20010508</enddate><creator>Bianco, Armandodoriano</creator><creator>Brufani, Mario</creator><creator>Manna, Fedele</creator><creator>Melchioni, Cristiana</creator><general>Elsevier Ltd</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>20010508</creationdate><title>Synthesis of a carbocyclic sialic acid analogue for the inhibition of influenza virus neuraminidase</title><author>Bianco, Armandodoriano ; Brufani, Mario ; Manna, Fedele ; Melchioni, Cristiana</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c361t-5c18b2f7247d104b95c80b74ed9355ee9e0d2e2165d4d05508d0773375f01cf23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Acetamides - pharmacology</topic><topic>Antiviral agents</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Guanidines - pharmacology</topic><topic>Neuraminidase - antagonists & inhibitors</topic><topic>Orthomyxoviridae - enzymology</topic><topic>Shikimic acid</topic><topic>Sialic acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bianco, Armandodoriano</creatorcontrib><creatorcontrib>Brufani, Mario</creatorcontrib><creatorcontrib>Manna, Fedele</creatorcontrib><creatorcontrib>Melchioni, Cristiana</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>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bianco, Armandodoriano</au><au>Brufani, Mario</au><au>Manna, Fedele</au><au>Melchioni, Cristiana</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of a carbocyclic sialic acid analogue for the inhibition of influenza virus neuraminidase</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2001-05-08</date><risdate>2001</risdate><volume>332</volume><issue>1</issue><spage>23</spage><epage>31</epage><pages>23-31</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>The influenza virus neuraminidase (NA) is essential for viral infection and offers a potential target for antiviral drug development. We prepared a carbocyclic sialic acid analogue, potentially able to inhibit NA. Its structure is an analogue of the transition-state of the reaction catalysed by NA. As starting material, quinic acid was selected owing to its ready availability and its stereochemical feature suitable for the target structure. The quinic acid was first converted in the shikimic acid; then two of the three hydroxyl functions of this product were selectively functionalised to obtain the target molecule (3
R,4
S,5
R)-4-acetamido-3-guanidino-5-hydroxycyclohex-1-ene-1-carboxylic acid.
A carbocyclic sialic acid analogue
17, potentially able to inhibit neuraminidase (NA), was prepared. Its structure in an analogue of the transition state of the reaction catalysed by NA.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>11403085</pmid><doi>10.1016/S0008-6215(01)00079-9</doi><tpages>9</tpages></addata></record> |
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| ispartof | Carbohydrate research, 2001-05, Vol.332 (1), p.23-31 |
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| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Acetamides - pharmacology Antiviral agents Antiviral Agents - chemical synthesis Enzyme Inhibitors - chemical synthesis Guanidines - pharmacology Neuraminidase - antagonists & inhibitors Orthomyxoviridae - enzymology Shikimic acid Sialic acid |
| title | Synthesis of a carbocyclic sialic acid analogue for the inhibition of influenza virus neuraminidase |
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