Design, Synthesis, Antioxidant and Anticancer Activity of Novel Schiff’s Bases of 2-Amino Benzothiazole

Abstract:

Introduction: Around 5,00,000 women are affected by cervical cancer and nearly half of them end up losing the battle of life with this deadly disease. So, there is an urgent need for the synthesis and development of new, small, synthetic molecules to tackle this challenge. Schiff’s bases are derivatives of azomethine group (-CH=N-) and are highly reactive. Here a series of novel Schiff’s bases were synthesized by single step process of condensing substituted 2-amino benzothiazole with different benzaldehydes. Objectives: To design, synthesize novel Schiff’s bases of 2-amino benzothiazole and evaluate its anti-oxidant as well as anti-cancer activity. Methods: A total of 18 compounds were synthesized by single step process of condensing substituted 2-amino benzothiazole with different substituted benzaldehydes. These were characterized by FTIR, 1H NMR, and Mass spectroscopy. The synthesized compounds were tested in-vitro for both antioxidant and antiproliferative activity. In-silico docking studies were performed on the crystal structure of the complex of caspase-3 with a nicotinic acid aldehyde inhibitor with PDB IDs 1RE1, 1RHM and 3DEH to study the interaction of the compounds with the receptor. Results: Majority of the derivatives displayed moderate to significant antiproliferative activity on HeLa cell line. Interestingly, the compound SP16 showed excellent activity with an IC₅₀ value of 2.517μg/ml in comparison to the reference compound Cisplatin (17.2μg/ml). Compound SP7 and SP 15 showed favourable in silico interactions.Conclusion: A series of 18 novel Schiff’s bases of 2-amino benzothiazoles compounds were designed, synthesized and evaluated for their biological activities. The compound SP16 showed excellent activity with an IC50 value of 2.517μg/ml in comparison to the reference compound Cisplatin and Compound SP7 and SP 15 showed favourable in silico interactions.

Key words: Schiff’s base, Anti-cancer activity, HeLa, 1RE1, 1RHM, 3DEH, Antioxidant activity.