Synthesis and biological activities of chloroethylurea, methylurea, and nitrosourea analogs of N-deacetylmethylthiocolchicine
A series of urea and nitrosourea analogues of N-deacetylmethylthiocolchicine (1) has been synthesized, and their antineoplastic and antiviral activities were evaluated. The objective for combination of two active moieties, such as thiocolchicine and nitrosourea, into one molecule was the generation...
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| Veröffentlicht in: | Journal of medicinal chemistry 1980-12, Vol.23 (12), p.1440-1442 |
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| container_issue | 12 |
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| container_title | Journal of medicinal chemistry |
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| creator | Lin, Tai-Shun Shiau, George T Prusoff, William H Harmon, Robert E |
| description | A series of urea and nitrosourea analogues of N-deacetylmethylthiocolchicine (1) has been synthesized, and their antineoplastic and antiviral activities were evaluated. The objective for combination of two active moieties, such as thiocolchicine and nitrosourea, into one molecule was the generation of compounds with potential improved biological and pharmacological properties. The ED50 for 2, 3, 4, and 5 was 1.6, 1.2, 3.3, and 1.8 X 10(-8) M for L1210 cells and 3.0, 2.7, 2.9, and 2.6 X 10(-8) M for S-180 cells, respectively. The synthesis and cytotoxic and antiviral properties of these compounds are discussed. |
| doi_str_mv | 10.1021/jm00186a028 |
| format | Article |
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The objective for combination of two active moieties, such as thiocolchicine and nitrosourea, into one molecule was the generation of compounds with potential improved biological and pharmacological properties. The ED50 for 2, 3, 4, and 5 was 1.6, 1.2, 3.3, and 1.8 X 10(-8) M for L1210 cells and 3.0, 2.7, 2.9, and 2.6 X 10(-8) M for S-180 cells, respectively. The synthesis and cytotoxic and antiviral properties of these compounds are discussed.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00186a028</identifier><identifier>PMID: 6256551</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Antineoplastic Agents - chemical synthesis ; Antiviral Agents - chemical synthesis ; Cells, Cultured ; Colchicine - analogs & derivatives ; Colchicine - chemical synthesis ; Mice ; Nitrosourea Compounds - chemical synthesis ; Simplexvirus - drug effects</subject><ispartof>Journal of medicinal chemistry, 1980-12, Vol.23 (12), p.1440-1442</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a420t-69e754ca2b9278edf8e402f7b6da83c043ee2e75212d3aee573d03226716e89a3</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/jm00186a028$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00186a028$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,782,786,2767,27083,27931,27932,56745,56795</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6256551$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lin, Tai-Shun</creatorcontrib><creatorcontrib>Shiau, George T</creatorcontrib><creatorcontrib>Prusoff, William H</creatorcontrib><creatorcontrib>Harmon, Robert E</creatorcontrib><title>Synthesis and biological activities of chloroethylurea, methylurea, and nitrosourea analogs of N-deacetylmethylthiocolchicine</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of urea and nitrosourea analogues of N-deacetylmethylthiocolchicine (1) has been synthesized, and their antineoplastic and antiviral activities were evaluated. The objective for combination of two active moieties, such as thiocolchicine and nitrosourea, into one molecule was the generation of compounds with potential improved biological and pharmacological properties. The ED50 for 2, 3, 4, and 5 was 1.6, 1.2, 3.3, and 1.8 X 10(-8) M for L1210 cells and 3.0, 2.7, 2.9, and 2.6 X 10(-8) M for S-180 cells, respectively. The synthesis and cytotoxic and antiviral properties of these compounds are discussed.</description><subject>Animals</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Cells, Cultured</subject><subject>Colchicine - analogs & derivatives</subject><subject>Colchicine - chemical synthesis</subject><subject>Mice</subject><subject>Nitrosourea Compounds - chemical synthesis</subject><subject>Simplexvirus - drug effects</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1980</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1v1DAQxS0EKkvhxBkpJziUwHic2MkRqvJRVVDUIo6W15kQL05cYi9iD_zveMmq6oGTx36_96x5jD3l8IoD8tebEYA30gA299iK1whl1UB1n60AEEuUKB6yRzFuAEBwFEfsSGIt65qv2J-r3ZQGii4WZuqKtQs-fHfW-MLY5H655CgWoS_s4MMcKA07v53JvCzGO_PeObk0hxj2D_lucso_36eyI2Mp7fxiSIMLNng7OOsmeswe9MZHenI4j9nXd2fXpx_Ki8_vP56-uShNhZBK2ZKqK2tw3aJqqOsbqgB7tZadaYSFShBhRpBjJwxRrUQHAlEqLqlpjThmz5fcmzn83FJMenTRkvdmorCNWtWixVaJDJ4soM3LxJl6fTO70cw7zUHvy9Z3ys70s0Psdj1Sd8se2s16ueguJvp9K5v5h5ZKqFpfX17pBt-ef7n8xvV55l8svLFRb3KXucf435__Ah_4mHk</recordid><startdate>19801201</startdate><enddate>19801201</enddate><creator>Lin, Tai-Shun</creator><creator>Shiau, George T</creator><creator>Prusoff, William H</creator><creator>Harmon, Robert E</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>7X8</scope></search><sort><creationdate>19801201</creationdate><title>Synthesis and biological activities of chloroethylurea, methylurea, and nitrosourea analogs of N-deacetylmethylthiocolchicine</title><author>Lin, Tai-Shun ; Shiau, George T ; Prusoff, William H ; Harmon, Robert E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a420t-69e754ca2b9278edf8e402f7b6da83c043ee2e75212d3aee573d03226716e89a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1980</creationdate><topic>Animals</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Cells, Cultured</topic><topic>Colchicine - analogs & derivatives</topic><topic>Colchicine - chemical synthesis</topic><topic>Mice</topic><topic>Nitrosourea Compounds - chemical synthesis</topic><topic>Simplexvirus - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lin, Tai-Shun</creatorcontrib><creatorcontrib>Shiau, George T</creatorcontrib><creatorcontrib>Prusoff, William H</creatorcontrib><creatorcontrib>Harmon, Robert E</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>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lin, Tai-Shun</au><au>Shiau, George T</au><au>Prusoff, William H</au><au>Harmon, Robert E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological activities of chloroethylurea, methylurea, and nitrosourea analogs of N-deacetylmethylthiocolchicine</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1980-12-01</date><risdate>1980</risdate><volume>23</volume><issue>12</issue><spage>1440</spage><epage>1442</epage><pages>1440-1442</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>A series of urea and nitrosourea analogues of N-deacetylmethylthiocolchicine (1) has been synthesized, and their antineoplastic and antiviral activities were evaluated. The objective for combination of two active moieties, such as thiocolchicine and nitrosourea, into one molecule was the generation of compounds with potential improved biological and pharmacological properties. The ED50 for 2, 3, 4, and 5 was 1.6, 1.2, 3.3, and 1.8 X 10(-8) M for L1210 cells and 3.0, 2.7, 2.9, and 2.6 X 10(-8) M for S-180 cells, respectively. The synthesis and cytotoxic and antiviral properties of these compounds are discussed.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>6256551</pmid><doi>10.1021/jm00186a028</doi><tpages>3</tpages></addata></record> |
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| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1980-12, Vol.23 (12), p.1440-1442 |
| issn | 0022-2623 1520-4804 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Animals Antineoplastic Agents - chemical synthesis Antiviral Agents - chemical synthesis Cells, Cultured Colchicine - analogs & derivatives Colchicine - chemical synthesis Mice Nitrosourea Compounds - chemical synthesis Simplexvirus - drug effects |
| title | Synthesis and biological activities of chloroethylurea, methylurea, and nitrosourea analogs of N-deacetylmethylthiocolchicine |
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