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

• Published in: Journal of the Iranian Chemical Society Vol. 19; no. 4; pp. 1039 - 1048
• Main Authors: Kumar, Palanichamy Santhosh, Obadiah, Asir, Durairaj, Arulappan, Ramanathan, Subramanian, Vasanthkumar, Samuel
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01.04.2022; Springer Nature B.V
• Subjects: Acids; Analytical Chemistry; Antioxidants; Benzoic acid; Biochemistry; Biocompatibility; Carbazoles; Carboxylic acids; Chemical synthesis; Chemistry; Chemistry and Materials Science; Coupling (molecular); Doxorubicin; Evaluation; Inorganic Chemistry; Organic Chemistry; Original Paper; Physical Chemistry; Toxicity; Suzuki coupling; HeLa cell lines; Cytotoxicity; Palladium catalyst; 1,4-Naphthoquinone; Antioxidant activity
• ISSN: 1735-207X; 1735-2428
• DOI: 10.1007/s13738-021-02361-2

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 IC 50 value of cytotoxicity (against HeLa) when compared with other derivatives. All the IC 50 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