Interferon inducing activities of derivatives of 1,3-dimethyl-4-(3-dimethylaminopropylamino)-1H-pyrazolo(3,4-b)quinoline and related compounds.
Syntheses and interferon inducing acitivites are reported for 137 relatives of 1,3-dimethyl-4-(3-dimethylamino-propylamino)-1H-pyrazolo[3,4-b]quinoline (1). Three different generalized synthetic schemes for the preparation of pyrazolo[3,4-b]quinolines are presented and limitations contrasted. Other heterocyclic nuclei containing the 3-dimethylaminopropylamino side chain include pyridine, quinoline, acridine, pyrazolo[3,4-b]pyridine, pyrazolo[3,4-B][1,8]naphthyridine, pyrazolo[4',3':5,6]pyrido[2,3-d]pyrimidine, dipyrazolo[3,4-b:4',3'-e]pyridine, pyrrolo-[2,3-b]quinoline, isothiazolo[5,4-b]quinoline, and pyrido[2,3-h]pyrazolo[3,4-b]quinoline. Structural requirements for interferon induction in this series are discussed and two of the more active compounds (172 and 196) are compared directly with tilorone.
D000284:Administration, Oral; D000818:Animals; D005260:Female; D007274:Injections, Intraperitoneal; D007369:Interferon Inducers / Q000138:chemical synthesis*; D007372:Interferons / Q000097:blood; D051379:Mice; D011720:Pyrazoles / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology; D011804:Quinolines / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013994:Tilorone / Q000494:pharmacology; D010948:Viral Plaque Assay
D007369:Interferon Inducers; D011720:Pyrazoles; D011804:Quinolines; D007372:Interferons; D013994:Tilorone