Volume 19, Issue 43, January - June, 2025

Synthesis, characterization, anticancer, and antioxidant studies of new azo-Schiff compounds derived from 2-naphthol

Mariam Alwan Abdulridua^1♦, Hussein Ali Hussein ALSa’idy¹, Ali Esmail Al-Snafi²

¹Department of Pharmaceutical Chemistry, College of Pharmacy, University of Thi-Qar, Thi-Qar, 64001, Iraq
²Department of Pharmacology, College of medicine, University of Thi-Qar, Thi- Qar, 64001, Iraq

^♦Corresponding author
Department of pharmaceutical chemistry, college of pharmacy, University of Thi- Qar, Thi-Qar, 64001, Iraq

ABSTRACT

Two new 2-naphthol-thiazole-azo compound Schiff bases of potential antitumor and/or antioxidant influences were chemically synthesized. The synthesized Schiff bases structures were identified using elemental analysis (CHN), mass spectroscopy, Fourier transform infrared FTIR & 1HNMR spectral techniques. The geometrical optimization as well as electronic structure predications of our compounds were obtained using quantum chemical calculations through DFT/B3LYP/6-31+G (d). The computational analysis had demonstrated a close interaction between both theoretical and experimental data. Finally, compound (1) had been evaluated for its anticancer activity against MCF-7 and WRL68 cell lines, which had shown a good anticancer effect. However, the antioxidant activity of both compounds (1&2) is evaluated using DPPH scavenger and had demonstrated a good antioxidant activity. In conclusion, the inclusion of C3-𝛼-naphthyl-azo-thiazinyl nucleus was essential for exploiting both in vitro anticancer as well as antioxidant influences. Docking study had revealed that compound 2 had more binding affinity to Vegfr2 than compound 1 due to the additional binding interactions of compound 2 as compared to compound 1, however, both had shared hydrogen bonding interactions with the same amino acid, Glu 883 and Asp 1044 of sorafenib. Meanwhile, compound 2 had some of priority in binding affinity than compound 1 to the active site superoxide dismutase enzyme although interactions was weaker than that of ascorbic acid. In conclusion, the inclusion of C3-𝛼-naphthyl-azo-thiazinyl nucleus in the azo-Schiff base scaffold structure was essential for exploiting both in vitro anticancer as well as antioxidant influences.

Keywords: Schiff base, 2-naphthol, Azo, 2-amino-1,3-thiazole, antioxidant, anticancer.

Drug Discovery, 2025, 19(43), e3dd2037

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DOI: https://doi.org/10.54905/disssi.v19i43.e3dd2037

Published: 09 February 2025