N-acetylation of 2-aminobenzothiazoles with Acetic Acid for Evaluation of Antifungal Activity and In Silico Analysis
DOI:
https://doi.org/10.33084/jmd.v1i2.3142Keywords:
acetylating agent, benzothiazole, docking, fungal strainAbstract
Acetamides (S30A1 and S30) were synthesized from benzo[d]thiazol-2-amine and 6-nitrobenzo[d]thiazol-2-amine by direct use of acetic acid instead of acetylating agents. The usual acetylating agents, acetic anhydride and acetyl chloride are very unstable especially because of their high sensitivity to environmental moisture. Thus, acetylation by direct use of acetic acid was searched as an alternative approach for synthesizing acetanilides. In this study, acetamides were synthesized with a yield of 88% and 82% respectively. The synthesized compounds were then screened for antifungal activity. At a concentration of 300 µg/disc, S30A1 showed 18 mm, 28 mm, 20 mm, and 16 mm zone of inhibitions against Penicillium notatum, Candida albicans, Aspergillus flavus, and Aspergillus niger, respectively. The standard miconazole was used at 50 µg/disc concentration. An in silico analysis was done for the possible binding modes in the C. albicans N-myristoyltransferase enzyme.
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References
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6. Cano NH, Ballari MS, López AG, Santiago AN. New Synthesis and Biological Evaluation of Benzothiazole Derivates as Antifungal Agents. J Agric Food Chem. 2015;63(14):3681–6. doi:10.1021/acs.jafc.5b00150
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18. Rothweiler U, Stensen W, Brandsdal BO, Isaksson J, Leeson FA, Engh RA, et al. Probing the ATP-Binding Pocket of Protein Kinase DYRK1A with Benzothiazole Fragment Molecules. J Med Chem. 2016;59(21):9814–24. doi:10.1021/acs.jmedchem.6b01086
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21. Paul D, Sanap G, Shenoy S, Kalyane D, Kalia K, Tekade RK. Artificial intelligence in drug discovery and development. Drug Discov Today. 2021;26(1):80-93. doi:10.1016/j.drudis.2020.10.010
22. Lee H, Lim HK, Kim H. Hydration Thermodynamics of Non-Polar Aromatic Hydrocarbons: Comparison of Implicit and Explicit Solvation Models. Molecules. 2018;23(11):2927. doi:10.3390/molecules23112927
23. Rasulev B. Recent Developments in 3D QSAR and Molecular Docking Studies of Organic and Nanostructures. In: Leszczynski J, Kaczmarek-Kedziera A, Puzyn T, Papadopoulos MG, Reis H, Shukla MK, editors. Handbook of Computational Chemistry. Cham: Springer; 2017. p. 2133-61. doi:10.1007/978-3-319-27282-5_54
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Published
2021-12-30
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1.
Bepary S, Biswas BK, Ghosh P, Haque MA, De TQ. N-acetylation of 2-aminobenzothiazoles with Acetic Acid for Evaluation of Antifungal Activity and In Silico Analysis. J Mol Docking [Internet]. 2021Dec.30 [cited 2024Dec.22];1(2):78-83. Available from: https://journal.umpr.ac.id/index.php/jmd/article/view/3142
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