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Indian Journal of Pharmaceutical Education and ResearchNOW IN
Article

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

D. Saipriya1, Arun Prakash1, Suvarna G Kini1★, Varadaraj Bhatt G1, K Sreedhara Ranganath Pai2, Subhankar Biswas2, Mohammed Shameer K1★ Corresponding author

  1. 1Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, MAHE, Manipal, 576104, Karnataka, INDIA.
  2. 2Department of Pharmacology, Manipal College of Pharmaceutical Sciences, MAHE, Manipal, 576104, Karnataka, INDIA.

CORRESPONDENCE

Suvarna G Kini

Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, MAHE, Manipal, 576104, Karnataka, INDIA.

suvarna.gk@manipal.edu

Received: 06-12-2017; Revised: 17-05-2018; Accepted: 14-08-2018.

Volume 52, Issue 4S · pp. s333–s342 · PUBLISHED 2018 · DOI: 10.5530/ijper.52.4s.114

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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.

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    Saipriya, D., Prakash, A., Kini, S. G., G, V. B., Pai, K. S. R., Biswas, S., & K, M. S. (2018). Design, Synthesis, Antioxidant and Anticancer Activity of Novel Schiff’s Bases of 2-Amino Benzothiazole. Indian Journal of Pharmaceutical Education and Research, 52(4S), s333–s342. https://doi.org/10.5530/ijper.52.4s.114