Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives
A series of new S-adenosyl-L-homocysteine (AdoHcy) analogues with modifications to amino acid and nucleoside moieties was prepared via condensation of appropriate nucleoside precursors and suitably protected L-homocystine derivatives. The AdoHcy derivatives as well as the nucleoside precursors were...
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| Veröffentlicht in: | Journal of medicinal chemistry 1992-11, Vol.35 (24), p.4576-4583 |
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| container_end_page | 4583 |
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| container_issue | 24 |
| container_start_page | 4576 |
| container_title | Journal of medicinal chemistry |
| container_volume | 35 |
| creator | Serafinowski, Pawel Dorland, Erwin Harrap, Kenneth R Balzarini, Jan De Clercq, Erik |
| description | A series of new S-adenosyl-L-homocysteine (AdoHcy) analogues with modifications to amino acid and nucleoside moieties was prepared via condensation of appropriate nucleoside precursors and suitably protected L-homocystine derivatives. The AdoHcy derivatives as well as the nucleoside precursors were evaluated for their antiviral activity. Some of the compounds, in particular S-tubercidinyl-L-homocysteine propyl ester (36), N-(trifluoroacetyl)-S-tubercidinyl-L-homocysteine isopropyl ester (27), S-3'-deoxytubercidinyl-L-homocysteine (58), N-(trifluoracetyl)-S-tubercidinyl-L-homocysteine propyl ester (26), and N-(methoxyacetyl)-S-tubercidinyl-L-homocysteine ethyl ester (31) showed potent and selective activity against HSV, VV, and VSV. It is likely that they exert their antiviral effect via selective inhibition of the methyltransferases which are required for the maturation of viral mRNAs. |
| doi_str_mv | 10.1021/jm00102a010 |
| format | Article |
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It is likely that they exert their antiviral effect via selective inhibition of the methyltransferases which are required for the maturation of viral mRNAs.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00102a010</identifier><identifier>PMID: 1335077</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>AIDS/HIV ; Animals ; Antiviral Agents - chemical synthesis ; Antiviral Agents - pharmacology ; Cell Line ; HIV-1 - drug effects ; Humans ; Methyltransferases - antagonists & inhibitors ; Molecular Structure ; Rabbits ; S-Adenosylhomocysteine - analogs & derivatives ; Simplexvirus - drug effects ; Vaccinia virus - drug effects ; Vesicular stomatitis Indiana virus - drug effects</subject><ispartof>Journal of medicinal chemistry, 1992-11, Vol.35 (24), p.4576-4583</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a385t-55fa75798c78b31b6a20e25877a99e24dc3c0207d7540820912edc3cb073c8dd3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00102a010$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00102a010$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27074,27922,27923,56736,56786</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1335077$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Serafinowski, Pawel</creatorcontrib><creatorcontrib>Dorland, Erwin</creatorcontrib><creatorcontrib>Harrap, Kenneth R</creatorcontrib><creatorcontrib>Balzarini, Jan</creatorcontrib><creatorcontrib>De Clercq, Erik</creatorcontrib><title>Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of new S-adenosyl-L-homocysteine (AdoHcy) analogues with modifications to amino acid and nucleoside moieties was prepared via condensation of appropriate nucleoside precursors and suitably protected L-homocystine derivatives. The AdoHcy derivatives as well as the nucleoside precursors were evaluated for their antiviral activity. Some of the compounds, in particular S-tubercidinyl-L-homocysteine propyl ester (36), N-(trifluoroacetyl)-S-tubercidinyl-L-homocysteine isopropyl ester (27), S-3'-deoxytubercidinyl-L-homocysteine (58), N-(trifluoracetyl)-S-tubercidinyl-L-homocysteine propyl ester (26), and N-(methoxyacetyl)-S-tubercidinyl-L-homocysteine ethyl ester (31) showed potent and selective activity against HSV, VV, and VSV. It is likely that they exert their antiviral effect via selective inhibition of the methyltransferases which are required for the maturation of viral mRNAs.</description><subject>AIDS/HIV</subject><subject>Animals</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - pharmacology</subject><subject>Cell Line</subject><subject>HIV-1 - drug effects</subject><subject>Humans</subject><subject>Methyltransferases - antagonists & inhibitors</subject><subject>Molecular Structure</subject><subject>Rabbits</subject><subject>S-Adenosylhomocysteine - analogs & derivatives</subject><subject>Simplexvirus - drug effects</subject><subject>Vaccinia virus - drug effects</subject><subject>Vesicular stomatitis Indiana virus - drug effects</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1992</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1LxDAQhoMouq6ePAs96UGik6RpukcRP1lQXEXwErLpLHZtG026av-9WSrqQfCQZMj7zAw8hOwwOGTA2dG8BoiFidcKGTDJgaY5pKtkAMA55RkXG2QzhDkACMbFOllnQkhQakBuJ13TPmEoQ2KaIp62fCu9qRJjl1XbJW6WBFdj0uB7MqGmwMaFrqJj-uRqZ7vQYtlgUqAv30xswbBF1mamCrj99Q7J_dnp3ckFHV-fX54cj6kRuWyplDOjpBrlVuVTwaaZ4YBc5kqZ0Qh5WlhhgYMqlEwh5zBiHJd_U1DC5kUhhmSvn_vi3esCQ6vrMlisKtOgWwStRApSgfgXZJlS6VLMkBz0oPUuBI8z_eLL2vhOM9BL1fqX6kjvfo1dTGssftjebcxpn5fR0cd3bPyzzpRQUt_dTPTVo8gebuAqdg3Jfs8bG_TcLXwT7f25-RPqJ5P0</recordid><startdate>19921101</startdate><enddate>19921101</enddate><creator>Serafinowski, Pawel</creator><creator>Dorland, Erwin</creator><creator>Harrap, Kenneth R</creator><creator>Balzarini, Jan</creator><creator>De Clercq, Erik</creator><general>American Chemical Society</general><scope>BSCLL</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>7TM</scope><scope>7X8</scope></search><sort><creationdate>19921101</creationdate><title>Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives</title><author>Serafinowski, Pawel ; Dorland, Erwin ; Harrap, Kenneth R ; Balzarini, Jan ; De Clercq, Erik</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a385t-55fa75798c78b31b6a20e25877a99e24dc3c0207d7540820912edc3cb073c8dd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1992</creationdate><topic>AIDS/HIV</topic><topic>Animals</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - pharmacology</topic><topic>Cell Line</topic><topic>HIV-1 - drug effects</topic><topic>Humans</topic><topic>Methyltransferases - antagonists & inhibitors</topic><topic>Molecular Structure</topic><topic>Rabbits</topic><topic>S-Adenosylhomocysteine - analogs & derivatives</topic><topic>Simplexvirus - drug effects</topic><topic>Vaccinia virus - drug effects</topic><topic>Vesicular stomatitis Indiana virus - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Serafinowski, Pawel</creatorcontrib><creatorcontrib>Dorland, Erwin</creatorcontrib><creatorcontrib>Harrap, Kenneth R</creatorcontrib><creatorcontrib>Balzarini, Jan</creatorcontrib><creatorcontrib>De Clercq, Erik</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Serafinowski, Pawel</au><au>Dorland, Erwin</au><au>Harrap, Kenneth R</au><au>Balzarini, Jan</au><au>De Clercq, Erik</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1992-11-01</date><risdate>1992</risdate><volume>35</volume><issue>24</issue><spage>4576</spage><epage>4583</epage><pages>4576-4583</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>A series of new S-adenosyl-L-homocysteine (AdoHcy) analogues with modifications to amino acid and nucleoside moieties was prepared via condensation of appropriate nucleoside precursors and suitably protected L-homocystine derivatives. The AdoHcy derivatives as well as the nucleoside precursors were evaluated for their antiviral activity. Some of the compounds, in particular S-tubercidinyl-L-homocysteine propyl ester (36), N-(trifluoroacetyl)-S-tubercidinyl-L-homocysteine isopropyl ester (27), S-3'-deoxytubercidinyl-L-homocysteine (58), N-(trifluoracetyl)-S-tubercidinyl-L-homocysteine propyl ester (26), and N-(methoxyacetyl)-S-tubercidinyl-L-homocysteine ethyl ester (31) showed potent and selective activity against HSV, VV, and VSV. It is likely that they exert their antiviral effect via selective inhibition of the methyltransferases which are required for the maturation of viral mRNAs.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>1335077</pmid><doi>10.1021/jm00102a010</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1992-11, Vol.35 (24), p.4576-4583 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_73405703 |
| source | MEDLINE; ACS Publications |
| subjects | AIDS/HIV Animals Antiviral Agents - chemical synthesis Antiviral Agents - pharmacology Cell Line HIV-1 - drug effects Humans Methyltransferases - antagonists & inhibitors Molecular Structure Rabbits S-Adenosylhomocysteine - analogs & derivatives Simplexvirus - drug effects Vaccinia virus - drug effects Vesicular stomatitis Indiana virus - drug effects |
| title | Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives |
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