New synthetic routes to tilorone dihydrochloride and some of its analogs
New synthetic routes to the orally active, interferon-inducing antiviral agent tilorone dihydrochloride, 2,7-bis-[(diethylamino)ethoxy]fluoren-9-one dihydrochloride (1a), were developed. The routes involved the preparation and solvolysis of tetrazonium fluoroborate salts of 2,7-diaminofluoren-9-one....
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| Veröffentlicht in: | Journal of medicinal chemistry 1978-10, Vol.21 (10), p.1084-1086 |
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| container_end_page | 1086 |
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| container_issue | 10 |
| container_start_page | 1084 |
| container_title | Journal of medicinal chemistry |
| container_volume | 21 |
| creator | Burke, Helen M Joullie, Madeleine M |
| description | New synthetic routes to the orally active, interferon-inducing antiviral agent tilorone dihydrochloride, 2,7-bis-[(diethylamino)ethoxy]fluoren-9-one dihydrochloride (1a), were developed. The routes involved the preparation and solvolysis of tetrazonium fluoroborate salts of 2,7-diaminofluoren-9-one. Nonplanar (1b), 9-sulfone (1c), and fluorene (1d) analogues of tilorone dihydrochloride were also prepared. Compounds 1b and 1c were evaluated for interferon induction. |
| doi_str_mv | 10.1021/jm00208a016 |
| format | Article |
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Med. Chem</addtitle><description>New synthetic routes to the orally active, interferon-inducing antiviral agent tilorone dihydrochloride, 2,7-bis-[(diethylamino)ethoxy]fluoren-9-one dihydrochloride (1a), were developed. The routes involved the preparation and solvolysis of tetrazonium fluoroborate salts of 2,7-diaminofluoren-9-one. Nonplanar (1b), 9-sulfone (1c), and fluorene (1d) analogues of tilorone dihydrochloride were also prepared. Compounds 1b and 1c were evaluated for interferon induction.</description><subject>Animals</subject><subject>Female</subject><subject>Fluorenes - chemical synthesis</subject><subject>Interferon Inducers - chemical synthesis</subject><subject>Mice</subject><subject>Molecular Conformation</subject><subject>Tilorone - analogs & derivatives</subject><subject>Tilorone - chemical synthesis</subject><subject>Tilorone - pharmacology</subject><subject>Tilorone - toxicity</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1978</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkL1PwzAQxS3EVylMrAzeGFDgbCd2GKFAC1QFRJktO3ZpSlNXtivof49RUMXAdHrv_XSnewgdEzgnQMnFrAGgUCogfAt1SEEhy0vIt1En-TSjnLJ9dBDCDAAYoWwP7QpKBeEdNBjZTxzWizi1sa6wd6toA44Ox3ruvFtYbOrp2nhXTZOujcVqYXBwjcVugusYklZz9x4O0c5EzYM9-p1d9HZ3O-4NsuFT_753NcwUK1jMDBSMEWKMKZLBgQmlcsU50doaU5XU5poVmlzmoBTVlJdQKC1Ac1KBgIp10Vm7t_IuBG8ncunrRvm1JCB_2pB_2kj0SUsvV7qxZsO276c4a-M6RPu1SZX_kFwwUcjx86t8ebx5ENflSPYTf9ryqgpy5lY-_R7-PfwNdKJ1ug</recordid><startdate>197810</startdate><enddate>197810</enddate><creator>Burke, Helen M</creator><creator>Joullie, Madeleine M</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>197810</creationdate><title>New synthetic routes to tilorone dihydrochloride and some of its analogs</title><author>Burke, Helen M ; Joullie, Madeleine M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a353t-d053311ddd5a356037aa4a661bbeddc82e4b35b1940aa2b26805ab70b61c070c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1978</creationdate><topic>Animals</topic><topic>Female</topic><topic>Fluorenes - chemical synthesis</topic><topic>Interferon Inducers - chemical synthesis</topic><topic>Mice</topic><topic>Molecular Conformation</topic><topic>Tilorone - analogs & derivatives</topic><topic>Tilorone - chemical synthesis</topic><topic>Tilorone - pharmacology</topic><topic>Tilorone - toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Burke, Helen M</creatorcontrib><creatorcontrib>Joullie, Madeleine M</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>Burke, Helen M</au><au>Joullie, Madeleine M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New synthetic routes to tilorone dihydrochloride and some of its analogs</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1978-10</date><risdate>1978</risdate><volume>21</volume><issue>10</issue><spage>1084</spage><epage>1086</epage><pages>1084-1086</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>New synthetic routes to the orally active, interferon-inducing antiviral agent tilorone dihydrochloride, 2,7-bis-[(diethylamino)ethoxy]fluoren-9-one dihydrochloride (1a), were developed. The routes involved the preparation and solvolysis of tetrazonium fluoroborate salts of 2,7-diaminofluoren-9-one. Nonplanar (1b), 9-sulfone (1c), and fluorene (1d) analogues of tilorone dihydrochloride were also prepared. Compounds 1b and 1c were evaluated for interferon induction.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>722716</pmid><doi>10.1021/jm00208a016</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1978-10, Vol.21 (10), p.1084-1086 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_jm00208a016 |
| source | MEDLINE; ACS Publications - Downers Grove, IL campus only. |
| subjects | Animals Female Fluorenes - chemical synthesis Interferon Inducers - chemical synthesis Mice Molecular Conformation Tilorone - analogs & derivatives Tilorone - chemical synthesis Tilorone - pharmacology Tilorone - toxicity |
| title | New synthetic routes to tilorone dihydrochloride and some of its analogs |
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