Synthesis, Structural Characterization and Anticancer Evaluation of 2-Aminobenzothiazole Derivative via Benzoyl Isothiocyanate

Siddhima Sharma; Lalima Sharma; Renu Rathore; D. Vijay; Mangal Shree Dulawat

doi:10.14233/ajchem.2025.33500

Issue

Vol. 37 No. 6 (2025): Vol 37 Issue 6, 2025

Issue Published : 27 May 2025

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Structural Characterization and Anticancer Evaluation of 2-Aminobenzothiazole Derivative via Benzoyl Isothiocyanate

https://doi.org/10.14233/ajchem.2025.33500

Siddhima Sharma

Department of Chemistry, J.R.N. Rajasthan Vidyapeeth (Deemed to be University), Udaipur-313001, India

https://orcid.org/0009-0008-8368-8459

Lalima Sharma

Department of Chemistry, J.R.N. Rajasthan Vidyapeeth (Deemed to be University), Udaipur-313001, India

Renu Rathore

Department of Chemistry, Faculty of Science, Bhupal Nobles’ University, Udaipur-313001, India

D. Vijay

Department of Physics, D.N.R College (A), Bhimavaram-534202, India

https://orcid.org/0000-0002-9457-0092

Mangal Shree Dulawat

Department of Chemistry, J.R.N. Rajasthan Vidyapeeth (Deemed to be University), Udaipur-313001, India

Corresponding Author(s) : Siddhima Sharma

siddhimasharma18@gmail.com

Asian Journal of Chemistry, Vol. 37 No. 6 (2025): Vol 37 Issue 6, 2025
Article Published : 27 May 2025

Abstract

2-Aminobenzothiazole derivatives are well-established scaffolds in medicinal chemistry, valued for their diverse pharmacological profiles. In this study, a novel synthetic route led to the development of N-(1,3-benzothiazol-2-yl)benzamide (SIBO), whose structure was thoroughly characterized via FTIR, NMR, HRMS and SC-XRD techniques. The experimentally determined crystal geometry was further supported by DFT calculations at the B3LYP/6-31G(d,p) level, showing excellent agreement in bond parameters and a moderate HOMO–LUMO energy gap indicative of potential bioactivity. Hirshfeld surface analysis highlighted key intermolecular interactions contributing to the stability of the crystal lattice. Preliminary in vitro cytostatic screening against MDA-MB-231 and MCF-7 breast cancer cell lines revealed dose-dependent growth inhibition, with SIBO reducing MDA-MB-231 cell viability by up to 52% at 10 µg/mL. Although its efficacy was lower to that of standard adriamycin, the selective activity and structural simplicity of SIBO indicate its potential as a lead compound for the development of safer and tailored anticancer drugs.

Keywords

2-Aminobenzothiazole DFT calculations Hirshfeld surface analysis Breast cancer cell lines Anticancer activity

(1)

Sharma, S.; Sharma, L.; Rathore, R.; Vijay, D.; Dulawat, M. S. Synthesis, Structural Characterization and Anticancer Evaluation of 2-Aminobenzothiazole Derivative via Benzoyl Isothiocyanate. ajc 2025, 37, 1509-1517.

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T.L. Dadmal, S.D. Katre, M.C. Mandewale and R.M. Kumbhare, New J. Chem., 42, 776 (2018); https://doi.org/10.1039/C7NJ03776G

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L.V. Zhilitskaya, B.A. Shainyan and N.O. Yarosh, Molecules, 26, 2190 (2021); https://doi.org/10.3390/molecules26082190

M. Neetha, S.B. Umabharathi and G. Anilkumar, Catal. Lett., 155, 15 (2025); https://doi.org/10.1007/s10562-024-04835-3

R. Javahershenas, J. Han, M. Kazemi and P.J. Jervis, ChemistryOpen, 13, e202400185 (2024); https://doi.org/10.1002/open.202400185

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C.C. Hoch, M. Shoykhet, T. Weiser, L. Griesbaum, J. Petry, K. Hachani, G. Multhoff, A. Bashiri Dezfouli and B. Wollenberg, Pharmacol. Res., 201, 107107 (2024); https://doi.org/10.1016/j.phrs.2024.107107

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M.A. Spackman and D. Jayatilaka, CrystEngComm, 11, 19 (2009); https://doi.org/10.1039/B818330A

J. Angulo-Cornejo, M. Lino-Pacheco, R. Richter, L. Hennig, K.-H. Hallmeier and L. Beyer, Inorg. Chim. Acta, 305, 38 (2000); https://doi.org/10.1016/S0020-1693(00)00109-2

V. Vichai and K. Kirtikara, Nat. Protoc., 1, 1112 (2006); https://doi.org/10.1038/nprot.2006.179

F. Corbo, A. Carocci, D. Armenise, N. De Laurentis, A. Laghezza, F. Loiodice, P. Ancona, M. Muraglia, V. Pagliarulo, C. Franchini and A. Catalano, J. Chem., 2016, 1 (2016); https://doi.org/10.1155/2016/4267564

A. Irfan, F. Batool, S.A.Z. Naqvi, A. Islam, S.M. Osman, A. Nocentini, S.A. Alissa and C.T. Supuran, J. Enzyme Inhib. Med. Chem., 35, 265 (2020); https://doi.org/10.1080/14756366.2019.1698036

Author biographies is not available.