Synthesis of N-(6-chloro-7-R-1,1-dioxo-1,4,2-benzodithiazin-3- yl)aminoacetaldehyde dimethyl acetals and their transformations into 8-chloroimidazo [1,2-b][1,4,2]benzodithiazine 5,5-dioxide derivatives with potential anti-HIV or anticancer activity.
A series of N-(6-chloro-7-R-1,1-dioxo-1,4,2-benzodithiazin-3- yl)aminoacetaldehyde dimethyl acetals [IIa-IIh] was obtained by the reaction of 6-chloro-7-R-3-methylthio-1,4,2-benzodithiazine 1,1-dioxides [Ia-Ih] with aminoacetaldehyde dimethyl acetal. Cyclization of benzodithiazinylaminoacetaldehyde dimethyl acetals [IIa-IIh] with 98% sulfuric acid gave the appropriate 7-substituted 8-chloroimidazo[1,2-b][1,4,2]benzodithiazine 5,5-dioxides [IIIa-IIIh] in good to high yields. The structures of these compounds were established on the basis of elemental analysis and spectral data (IR, 1H and 13C NMR). Preliminary screening data indicated that compound [IIIa] exhibit moderate anti-HIV activity, and compounds [IIId-IIIg] anticancer activity.
Brzozowski
Z
Z
Department of Drug Technology, Faculty of Farmacy, Medical University, Gdańsk, Poland.
D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013843:Thiazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000080:Acetals; D000970:Antineoplastic Agents; D013843:Thiazines