Isoquinolines. 6. Potential central nervous system antitumor agents. Nitrogen mustards of 3-amino-4-(p-aminophenyl)isoquinoline
A series of 3-amino-4-(p-aminophenyl)isoquinolines bearing the bis(2-chloroethyl)amino group was synthesized as potential CNS antitumor agents. Diol precursors 1e and 1f were prepared by the treatment of 1b and 1c with ethylene oxide. Diol precursors 5a-c and 9 were prepared by the treatment of 4a-c...
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| Veröffentlicht in: | Journal of medicinal chemistry 1977-11, Vol.20 (11), p.1504-1508 |
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| container_end_page | 1508 |
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| container_issue | 11 |
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| container_title | Journal of medicinal chemistry |
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| creator | Filer, Crist N Granchelli, Felix E Soloway, Albert H Neumeyer, John L |
| description | A series of 3-amino-4-(p-aminophenyl)isoquinolines bearing the bis(2-chloroethyl)amino group was synthesized as potential CNS antitumor agents. Diol precursors 1e and 1f were prepared by the treatment of 1b and 1c with ethylene oxide. Diol precursors 5a-c and 9 were prepared by the treatment of 4a-c and 8 with diethanolamine. The reaction of these diols with SOCl2 yielded target mustards 10-15 which were evaluated in the intraperitoneal murine L1210 tumor. No intermediates or target mustards were active in this tumor system. |
| doi_str_mv | 10.1021/jm00221a030 |
| format | Article |
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Potential central nervous system antitumor agents. Nitrogen mustards of 3-amino-4-(p-aminophenyl)isoquinoline</title><source>MEDLINE</source><source>ACS Publications</source><creator>Filer, Crist N ; Granchelli, Felix E ; Soloway, Albert H ; Neumeyer, John L</creator><creatorcontrib>Filer, Crist N ; Granchelli, Felix E ; Soloway, Albert H ; Neumeyer, John L</creatorcontrib><description>A series of 3-amino-4-(p-aminophenyl)isoquinolines bearing the bis(2-chloroethyl)amino group was synthesized as potential CNS antitumor agents. Diol precursors 1e and 1f were prepared by the treatment of 1b and 1c with ethylene oxide. Diol precursors 5a-c and 9 were prepared by the treatment of 4a-c and 8 with diethanolamine. The reaction of these diols with SOCl2 yielded target mustards 10-15 which were evaluated in the intraperitoneal murine L1210 tumor. No intermediates or target mustards were active in this tumor system.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00221a030</identifier><identifier>PMID: 915914</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkylating Agents - chemical synthesis ; Alkylating Agents - therapeutic use ; Animals ; Blood-Brain Barrier ; Isoquinolines - chemical synthesis ; Isoquinolines - therapeutic use ; Leukemia L1210 - drug therapy ; Mice ; Nitrogen Mustard Compounds - chemical synthesis ; Nitrogen Mustard Compounds - therapeutic use</subject><ispartof>Journal of medicinal chemistry, 1977-11, Vol.20 (11), p.1504-1508</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a268t-4f90c21456e3db86686b3dfbda1b7fba8b53130c4f51bb12ffb12dd88816d72d3</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/jm00221a030$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00221a030$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/915914$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Filer, Crist N</creatorcontrib><creatorcontrib>Granchelli, Felix E</creatorcontrib><creatorcontrib>Soloway, Albert H</creatorcontrib><creatorcontrib>Neumeyer, John L</creatorcontrib><title>Isoquinolines. 6. Potential central nervous system antitumor agents. Nitrogen mustards of 3-amino-4-(p-aminophenyl)isoquinoline</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of 3-amino-4-(p-aminophenyl)isoquinolines bearing the bis(2-chloroethyl)amino group was synthesized as potential CNS antitumor agents. Diol precursors 1e and 1f were prepared by the treatment of 1b and 1c with ethylene oxide. Diol precursors 5a-c and 9 were prepared by the treatment of 4a-c and 8 with diethanolamine. The reaction of these diols with SOCl2 yielded target mustards 10-15 which were evaluated in the intraperitoneal murine L1210 tumor. No intermediates or target mustards were active in this tumor system.</description><subject>Alkylating Agents - chemical synthesis</subject><subject>Alkylating Agents - therapeutic use</subject><subject>Animals</subject><subject>Blood-Brain Barrier</subject><subject>Isoquinolines - chemical synthesis</subject><subject>Isoquinolines - therapeutic use</subject><subject>Leukemia L1210 - drug therapy</subject><subject>Mice</subject><subject>Nitrogen Mustard Compounds - chemical synthesis</subject><subject>Nitrogen Mustard Compounds - therapeutic use</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1977</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkElPwzAQhS3EVpYTVw6-AUIuHjtx0yOq2KQKKrFcLTu2IaWJi50geuKvYxSEOHCZN_L7ZkZ-CB0AHQJlcDavKWUMFOV0DQ0gZ5RkBc3W0eD7nTDB-DbaiXFOKeXA-BbaHEM-hmyAPm-if-uqxi-qxsYhFkM8861t2kotcJk0JG1sePddxHEVW1tjldy2q33A6jkRaeq2aoNPPa672KpgIvYOc6LqtJhk5HjZt8sX26wWJ9Wfk3tow6lFtPs_uoseLy8eJtdkend1MzmfEsVE0ZLMjWnJIMuF5UYXQhRCc-O0UaBHTqtC5xw4LTOXg9bAnEvFmKIoQJgRM3wXnfZ7y-BjDNbJZahqFVYSqPwOUf4JMdGHPb3sdG3NL9unlmzS21XK4-PXVeFVihEf5fJhdi9nUxhPnuBeXif-qOdVGeXcd6FJX_338BcO0IqR</recordid><startdate>19771101</startdate><enddate>19771101</enddate><creator>Filer, Crist N</creator><creator>Granchelli, Felix E</creator><creator>Soloway, Albert H</creator><creator>Neumeyer, John L</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></search><sort><creationdate>19771101</creationdate><title>Isoquinolines. 6. Potential central nervous system antitumor agents. Nitrogen mustards of 3-amino-4-(p-aminophenyl)isoquinoline</title><author>Filer, Crist N ; Granchelli, Felix E ; Soloway, Albert H ; Neumeyer, John L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a268t-4f90c21456e3db86686b3dfbda1b7fba8b53130c4f51bb12ffb12dd88816d72d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1977</creationdate><topic>Alkylating Agents - chemical synthesis</topic><topic>Alkylating Agents - therapeutic use</topic><topic>Animals</topic><topic>Blood-Brain Barrier</topic><topic>Isoquinolines - chemical synthesis</topic><topic>Isoquinolines - therapeutic use</topic><topic>Leukemia L1210 - drug therapy</topic><topic>Mice</topic><topic>Nitrogen Mustard Compounds - chemical synthesis</topic><topic>Nitrogen Mustard Compounds - therapeutic use</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Filer, Crist N</creatorcontrib><creatorcontrib>Granchelli, Felix E</creatorcontrib><creatorcontrib>Soloway, Albert H</creatorcontrib><creatorcontrib>Neumeyer, John L</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><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Filer, Crist N</au><au>Granchelli, Felix E</au><au>Soloway, Albert H</au><au>Neumeyer, John L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isoquinolines. 6. Potential central nervous system antitumor agents. Nitrogen mustards of 3-amino-4-(p-aminophenyl)isoquinoline</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1977-11-01</date><risdate>1977</risdate><volume>20</volume><issue>11</issue><spage>1504</spage><epage>1508</epage><pages>1504-1508</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>A series of 3-amino-4-(p-aminophenyl)isoquinolines bearing the bis(2-chloroethyl)amino group was synthesized as potential CNS antitumor agents. Diol precursors 1e and 1f were prepared by the treatment of 1b and 1c with ethylene oxide. Diol precursors 5a-c and 9 were prepared by the treatment of 4a-c and 8 with diethanolamine. The reaction of these diols with SOCl2 yielded target mustards 10-15 which were evaluated in the intraperitoneal murine L1210 tumor. No intermediates or target mustards were active in this tumor system.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>915914</pmid><doi>10.1021/jm00221a030</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1977-11, Vol.20 (11), p.1504-1508 |
| issn | 0022-2623 1520-4804 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Alkylating Agents - chemical synthesis Alkylating Agents - therapeutic use Animals Blood-Brain Barrier Isoquinolines - chemical synthesis Isoquinolines - therapeutic use Leukemia L1210 - drug therapy Mice Nitrogen Mustard Compounds - chemical synthesis Nitrogen Mustard Compounds - therapeutic use |
| title | Isoquinolines. 6. Potential central nervous system antitumor agents. Nitrogen mustards of 3-amino-4-(p-aminophenyl)isoquinoline |
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