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Synthesis of Derivatives of the 2-Arylquinoline Alkaloid Dubamine and their Cytotoxicity

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5′-Nitro- ( 2 ) and 5′-aminodubamine ( 3 ) were sequentially synthesized from the alkaloid dubamine. Condensation of 3 with 15 aldehydes gave imines, reduction of which produced secondary amines.… Click to show full abstract

5′-Nitro- ( 2 ) and 5′-aminodubamine ( 3 ) were sequentially synthesized from the alkaloid dubamine. Condensation of 3 with 15 aldehydes gave imines, reduction of which produced secondary amines. Studies of the cytotoxicities for HeLa and HEp-2 cells of the compounds at a concentration of 100 μM revealed several trends. The activity decreased significantly or disappeared at lower concentrations although compound 5o at concentrations of 1–10 μM was active for HEp-2 cells at the level of cisplatin.

Keywords: alkaloid dubamine; dubamine cytotoxicity; arylquinoline alkaloid; dubamine; synthesis derivatives; derivatives arylquinoline

Journal Title: Chemistry of Natural Compounds
Year Published: 2020

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