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

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Abstract

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.

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Acknowledgements

The authors thank the management and the authorities of Karunya Institute of Technology and Science, Coimbatore, for their kind support and constant encouragement. We extend our thanks to SAIF, IIT Madras, India, for NMR and mass spectral analysis.

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Authors and Affiliations

  1. Department of Applied Chemistry, Karunya Institute of Technology and Science, Coimbatore, 641114, India

    Palanichamy Santhosh Kumar, Asir Obadiah, Arulappan Durairaj, Subramanian Ramanathan & Samuel Vasanthkumar

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  1. Palanichamy Santhosh Kumar
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  2. Asir Obadiah
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  3. Arulappan Durairaj
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  4. Subramanian Ramanathan
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  5. Samuel Vasanthkumar
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Correspondence to Samuel Vasanthkumar.

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Kumar, P.S., Obadiah, A., Durairaj, A. et al. Synthesis and bioactivity evaluation of 3-amino-6, 11-dioxo-6, 11-dihydro-5H-benzo[b]carbazole-1-carboxylic acid derivatives. J IRAN CHEM SOC 19, 1039–1048 (2022). https://doi.org/10.1007/s13738-021-02361-2

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