Derivatives of benzo(c)fluorene: II. Synthesis and biological effect of basic ethers of 7-oxo-7H-benzo(c)fluorene

Abstract

Alkylation of phenols IIa-IIc with ω-(N,N-dialkylamino)alkyl chlorides IIIa-IIId in an aqueous and/or a two-phase (toluene and aqueous potassium hydroxide) medium, and reactions of phenols IId-IIf with isopropylamine, gave rise to ethers IV-XIX. Compounds IV and V were used to prepare derivatives XX-XXVI. Reduction of the 7-oxo group in the compound V by the action of sodium borohydride produced the 7-hydroxy derivatives XXIV-XXVI, whereas reduction under conditions of the Wolf-Kishner reaction led to derivatives XXVII and XXVIII, respectively, which were also obtained by alkylation of XXIX with IIIa in an anhydrous medium. The compound XXIX was prepared by reduction of compound IIa. Most the of compounds prepared had marked antineoplastic effects, particularly compounds IV and V. Compounds V, VII, IX and XVIII exhibited antibacterial effects, and compounds XVI, XVIII and XXIII were as efficacious in subcutaneous application against encephalomyocarditis virus as Tiloron, used as standard.