Synthesis and bioactivity evaluation of 3-amino-6, 11-dioxo-6, 11-dihydro-5H-benzo[b]carbazole-1-carboxylic acid derivatives

A series of 3-amino-5-(1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)benzoic acid derivatives were synthesized by the Michael addition of 1,4-naphthoquinone and 3,5-diaminobenzoic acid followed by the Suzuki coupling reaction. The derivatives of compound 2 were integrated, exposing it to benzolyation by an assortment of acid chlorides. Among the synthesized compounds, compounds 3b, 3c and 3d displayed better IC₅₀ value of cytotoxicity (against HeLa) when compared with other derivatives. All the IC₅₀ esteems were compared with the standard drug doxorubicin. DPPH and ABTS evaluation procedures are employed to assess the antioxidant activity. The compound 3d exhibited the highest inhibition of 75% and 77% in the DPPH and ABTS antioxidant activity evaluation, respectively. Graphic abstract: [Figure not available: see fulltext.]