Ergot alkaloids. Synthesis of nitrosourea derivatives of ergolines as potential anticancer agents
Nitrosourea derivatives of ergolines have been synthesized for the purpose of obtaining agents with both prolactin-and tumor-inhibitory activity. Two derivatives of 8-amino-6-methylergoline (3), 8-[3-(2-chloroethyl)-3-nitrosoureido]-1-nitroso-6-methylergoline (5c) and 8-[3-2-chloroethyl)-3-nitrosour...
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| Veröffentlicht in: | Journal of medicinal chemistry 1979-01, Vol.22 (1), p.32-35 |
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| container_title | Journal of medicinal chemistry |
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| creator | Crider, A. Michael Lu, Catherine K. L Floss, Heinz G Cassady, John M Clemens, James A |
| description | Nitrosourea derivatives of ergolines have been synthesized for the purpose of obtaining agents with both prolactin-and tumor-inhibitory activity. Two derivatives of 8-amino-6-methylergoline (3), 8-[3-(2-chloroethyl)-3-nitrosoureido]-1-nitroso-6-methylergoline (5c) and 8-[3-2-chloroethyl)-3-nitrosoureido]-6-methylergoline (5a), have been prepared. In addition, nitroso (7) and chloroethylcarbamyl (8) derivatives of elymoclavine (6) are reported. Compounds 5a and 5c have activity against L1210 leukemia in mice but only moderate prolactin-inhibiting activity. The chloroethylcarbamyl derivative 8 of elymoclavine is a potent prolacting inhibitor. |
| doi_str_mv | 10.1021/jm00187a008 |
| format | Article |
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Synthesis of nitrosourea derivatives of ergolines as potential anticancer agents</title><source>ACS Publications</source><source>MEDLINE</source><creator>Crider, A. Michael ; Lu, Catherine K. L ; Floss, Heinz G ; Cassady, John M ; Clemens, James A</creator><creatorcontrib>Crider, A. Michael ; Lu, Catherine K. L ; Floss, Heinz G ; Cassady, John M ; Clemens, James A</creatorcontrib><description>Nitrosourea derivatives of ergolines have been synthesized for the purpose of obtaining agents with both prolactin-and tumor-inhibitory activity. Two derivatives of 8-amino-6-methylergoline (3), 8-[3-(2-chloroethyl)-3-nitrosoureido]-1-nitroso-6-methylergoline (5c) and 8-[3-2-chloroethyl)-3-nitrosoureido]-6-methylergoline (5a), have been prepared. In addition, nitroso (7) and chloroethylcarbamyl (8) derivatives of elymoclavine (6) are reported. Compounds 5a and 5c have activity against L1210 leukemia in mice but only moderate prolactin-inhibiting activity. The chloroethylcarbamyl derivative 8 of elymoclavine is a potent prolacting inhibitor.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00187a008</identifier><identifier>PMID: 423180</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Antineoplastic Agents - chemical synthesis ; Ergolines - chemical synthesis ; Ergolines - pharmacology ; Leukemia L1210 - drug therapy ; Mice ; Nitrosourea Compounds - chemical synthesis ; Nitrosourea Compounds - pharmacology ; Prolactin - metabolism ; Rats</subject><ispartof>Journal of medicinal chemistry, 1979-01, Vol.22 (1), p.32-35</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a268t-7b8665bf8a8e55aecc43f0a50c00e114a5aebd8ab09bd959c29756e0b9c058f3</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/jm00187a008$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00187a008$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/423180$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Crider, A. Michael</creatorcontrib><creatorcontrib>Lu, Catherine K. L</creatorcontrib><creatorcontrib>Floss, Heinz G</creatorcontrib><creatorcontrib>Cassady, John M</creatorcontrib><creatorcontrib>Clemens, James A</creatorcontrib><title>Ergot alkaloids. Synthesis of nitrosourea derivatives of ergolines as potential anticancer agents</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Nitrosourea derivatives of ergolines have been synthesized for the purpose of obtaining agents with both prolactin-and tumor-inhibitory activity. Two derivatives of 8-amino-6-methylergoline (3), 8-[3-(2-chloroethyl)-3-nitrosoureido]-1-nitroso-6-methylergoline (5c) and 8-[3-2-chloroethyl)-3-nitrosoureido]-6-methylergoline (5a), have been prepared. In addition, nitroso (7) and chloroethylcarbamyl (8) derivatives of elymoclavine (6) are reported. Compounds 5a and 5c have activity against L1210 leukemia in mice but only moderate prolactin-inhibiting activity. The chloroethylcarbamyl derivative 8 of elymoclavine is a potent prolacting inhibitor.</description><subject>Animals</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Ergolines - chemical synthesis</subject><subject>Ergolines - pharmacology</subject><subject>Leukemia L1210 - drug therapy</subject><subject>Mice</subject><subject>Nitrosourea Compounds - chemical synthesis</subject><subject>Nitrosourea Compounds - pharmacology</subject><subject>Prolactin - metabolism</subject><subject>Rats</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1979</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEFP3DAQRq0KCgvtqVcOOZVDFRg7duIcqxWloJVoYU-9WBNnAl6yyWJ7Ufn3uA1CHDiNZr43Y_kx9oXDCQfBT1drAK4rBNAf2IwrAbnUIHfYDECIXJSi2GcHIawAoOCi2GMfpSi4hhnDM387xgz7e-xH14aT7OZpiHcUXMjGLhtc9GMYt54wa8m7R4zukf5HlBZ7N6QGQ7YZIw3RYZ9hKhYHSz7D2zQLn9huh32gzy_1kC1_nC3nP_PF1fnF_PsiR1HqmFeNLkvVdBo1KYVkrSw6QAUWgDiXmGZNq7GBumlrVVtRV6okaGoLSnfFIfs6nd348WFLIZq1C5b6Hgcat8FUUvJSa5nAbxNo08-Cp85svFujfzIczD-d5o3ORB-9nN02a2pf2clfivMpdiHS39cU_b0pq6JSZvnrxvBL9XtxfS7Nn8QfTzzaYFbJ65CUvPvwM4YYjVs</recordid><startdate>197901</startdate><enddate>197901</enddate><creator>Crider, A. Michael</creator><creator>Lu, Catherine K. L</creator><creator>Floss, Heinz G</creator><creator>Cassady, John M</creator><creator>Clemens, James A</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>197901</creationdate><title>Ergot alkaloids. Synthesis of nitrosourea derivatives of ergolines as potential anticancer agents</title><author>Crider, A. Michael ; Lu, Catherine K. L ; Floss, Heinz G ; Cassady, John M ; Clemens, James A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a268t-7b8665bf8a8e55aecc43f0a50c00e114a5aebd8ab09bd959c29756e0b9c058f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1979</creationdate><topic>Animals</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Ergolines - chemical synthesis</topic><topic>Ergolines - pharmacology</topic><topic>Leukemia L1210 - drug therapy</topic><topic>Mice</topic><topic>Nitrosourea Compounds - chemical synthesis</topic><topic>Nitrosourea Compounds - pharmacology</topic><topic>Prolactin - metabolism</topic><topic>Rats</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Crider, A. Michael</creatorcontrib><creatorcontrib>Lu, Catherine K. L</creatorcontrib><creatorcontrib>Floss, Heinz G</creatorcontrib><creatorcontrib>Cassady, John M</creatorcontrib><creatorcontrib>Clemens, James A</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>Crider, A. Michael</au><au>Lu, Catherine K. L</au><au>Floss, Heinz G</au><au>Cassady, John M</au><au>Clemens, James A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ergot alkaloids. Synthesis of nitrosourea derivatives of ergolines as potential anticancer agents</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1979-01</date><risdate>1979</risdate><volume>22</volume><issue>1</issue><spage>32</spage><epage>35</epage><pages>32-35</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>Nitrosourea derivatives of ergolines have been synthesized for the purpose of obtaining agents with both prolactin-and tumor-inhibitory activity. Two derivatives of 8-amino-6-methylergoline (3), 8-[3-(2-chloroethyl)-3-nitrosoureido]-1-nitroso-6-methylergoline (5c) and 8-[3-2-chloroethyl)-3-nitrosoureido]-6-methylergoline (5a), have been prepared. In addition, nitroso (7) and chloroethylcarbamyl (8) derivatives of elymoclavine (6) are reported. Compounds 5a and 5c have activity against L1210 leukemia in mice but only moderate prolactin-inhibiting activity. The chloroethylcarbamyl derivative 8 of elymoclavine is a potent prolacting inhibitor.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>423180</pmid><doi>10.1021/jm00187a008</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1979-01, Vol.22 (1), p.32-35 |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Animals Antineoplastic Agents - chemical synthesis Ergolines - chemical synthesis Ergolines - pharmacology Leukemia L1210 - drug therapy Mice Nitrosourea Compounds - chemical synthesis Nitrosourea Compounds - pharmacology Prolactin - metabolism Rats |
| title | Ergot alkaloids. Synthesis of nitrosourea derivatives of ergolines as potential anticancer agents |
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