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Vol. 31 No. 12 (2019): Vol 31 Issue 12

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Synthesis, Structural Characterization and Biological Evaluation of 3-Amino-5-(5-oxo-5H-benzo[a]phenoxazin-6-ylamino)benzoic acid Derivatives

https://doi.org/10.14233/ajchem.2019.22253
Palanichamy Santhosh Kumar
Department of Chemistry, Karunya Institute of Technology and Science, Coimbatore-641114, India
Dhanaraj Premnath
Department of Bioinformatics, Karunya Institute of Technology and Science, Coimbatore-641114, India
Asir Obadiah
Department of Chemistry, Karunya Institute of Technology and Science, Coimbatore-641114, India
Arulappan Durairaj
Department of Chemistry, Karunya Institute of Technology and Science, Coimbatore-641114, India
Subramanian Ramanathan
Department of Chemistry, Karunya Institute of Technology and Science, Coimbatore-641114, India
Samuel Vasanthkumar
Department of Chemistry, Karunya Institute of Technology and Science, Coimbatore-641114, India

Corresponding Author(s) : Samuel Vasanthkumar

vasanthakumar@karunya.edu; kumar2359@yahoo.com

Asian Journal of Chemistry, Vol. 31 No. 12 (2019): Vol 31 Issue 12

Abstract

1,4-Naphthoquinones are exceptional building blocks in organic synthesis and have been used to synthesize several well-known pharmaceutically active agents. Compounds containing oxygen, nitrogen or sulfur atoms inside the rings are attracting much attention and interest due to their biological importance. A series of 3-amino-5-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)benzoic acid derivatives were synthesized by the Michael addition of 2,3-dichloronaphthalene-1,4-dione and 3,5-diaminobenzoic acid. All the synthesized compounds are screened for their bioactivity through molecular docking, cytotoxicity (against HeLa) and antioxidant activity. DPPH and ABTS evaluation procedures are employed to assess the antioxidant activity. Among the synthesized 3-amino-5-(3-chloro-1, 4-dioxo-1, 4-dihydronaphthalen-2-ylamino)benzoic acid derivatives (1, 2, 3a-g), compound 3d exhibited the highest inhibition of 75 % and 83 % in the DPPH and ABTS antioxidant activity evaluation, respectively. Compound 3d exhibited better glide energy and E model scores when docked with HDAC8 using GLIDE program. Cytotoxicity of the synthesized compounds was studied against cervical cancer cell line (HeLa) and compound 3d showed the maximum inhibition and displayed a better activity than the standard drug.

Keywords

Michael addition 2,3-Dichloronaphthalene-1,4-dione Molecular docking Cytotoxicity Antioxidant activity
Kumar, P. S., Premnath, D., Obadiah, A., Durairaj, A., Ramanathan, S., & Vasanthkumar, S. (2019). Synthesis, Structural Characterization and Biological Evaluation of 3-Amino-5-(5-oxo-5H-benzo[a]phenoxazin-6-ylamino)benzoic acid Derivatives. Asian Journal of Chemistry, 31(12), 2986–2994. https://doi.org/10.14233/ajchem.2019.22253
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