TY - JOUR
T1 - Synthesis and bioactivity evaluation of 3-amino-6, 11-dioxo-6, 11-dihydro-5H-benzo[b]carbazole-1-carboxylic acid derivatives
AU - Kumar, Palanichamy Santhosh
AU - Obadiah, Asir
AU - Durairaj, Arulappan
AU - Ramanathan, Subramanian
AU - Vasanthkumar, Samuel
N1 - Publisher Copyright:
© 2021, Iranian Chemical Society.
PY - 2022/4
Y1 - 2022/4
N2 - 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.]
AB - 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.]
KW - 1,4-Naphthoquinone
KW - Antioxidant activity
KW - Cytotoxicity
KW - HeLa cell lines
KW - Palladium catalyst
KW - Suzuki coupling
UR - http://www.scopus.com/inward/record.url?scp=85112821128&partnerID=8YFLogxK
U2 - 10.1007/s13738-021-02361-2
DO - 10.1007/s13738-021-02361-2
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AN - SCOPUS:85112821128
SN - 1735-207X
VL - 19
SP - 1039
EP - 1048
JO - Journal of the Iranian Chemical Society
JF - Journal of the Iranian Chemical Society
IS - 4
ER -