New synthetic routes to tilorone dihydrochloride and some of its analogues.
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.
D000818:Animals; D005260:Female; D005449:Fluorenes / Q000138:chemical synthesis*; D007369:Interferon Inducers / Q000138:chemical synthesis; D051379:Mice; D008968:Molecular Conformation; D013994:Tilorone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity
D005449:Fluorenes; D007369:Interferon Inducers; D013994:Tilorone