Synthesis And In Vitro Biological Evaluation Of Metal Complexes Of 2-Aminobenzothiazole
Keywords:
2-aminobenzothiazole, Schiff base, metal complexes, spectral analysis, biological evaluation and antioxidant activity
Abstract
Antibiotic resistance is a growing problem in today’s healthcare which increase the demand of heterocyclic compounds. Heterocyclic compound bears different biological activity, like anti-cancer, anti-inflammatory, anti-oxidant, antibacterial, etc. therefor its demand increase in development of new compounds to overcome microbial resistance. The coordination chemistry of 2-aminobenzothiazole, which possesses potential coordinating sites including one exocyclic (NH2) and two endocyclic (N and S), has received significant attention in recent decades. The interest has led to the discovery of various transition metal complexes exhibiting diverse structures. 2-amino benzothiazole and substituted aldehyde (2,4 dichlorbenzaldehyde ,4-benzyloxybenzaldehyde) used as a reactant in synthetic organic chemistry and also used for making Schiff base ligand for increase the potency of the final product. The reaction of the Schiff bases (SB1 and SB2) with the core metals like Cobalt chloride, manganese chloride, nickel chloride, and copper (II) has produced metal complexes (MC1-8) of Schiff bases. In our study, we employed the DPPH assay and the agar diffusion method to assess the anti-oxidant and antimicrobial characteristics of the synthesized ligands and their metal complexes
References
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23. Sunjuk, M., Al-Najjar, L., Shtaiwi, M., El‐Eswed, B., Al-Noaimi, M., Al‐Essa, L. Y., and Sweidan, K. (2022b). Transition Metal Complexes of Schiff Base Ligands Prepared from Reaction of Aminobenzothiazole with Benzaldehydes. Inorganics, 10(4), 43. https://doi.org/10.3390/inorganics10040043
24. Sunjuk, M., Al-Najjar, L., Shtaiwi, M., El‐Eswed, B., Al-Noaimi, M., Al‐Essa, L. Y., and Sweidan, K. (2022). Transition Metal Complexes of Schiff Base Ligands Prepared from Reaction of Aminobenzothiazole with Benzaldehydes. Inorganics (Basel), 10(4), 43. https://doi.org/10.3390/inorganics10040043
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2. Al‐Resayes, S. I., Jarad, A. J., Al-Zinkee, J. M. M., Al‐Noor, T. H., El‐ajaily, M. M., Abdalla, M., Kim, M., Azam, M., and Mohapatra, R. K. (2023). Synthesis, characterization, antimicrobial studies, and molecular docking studies of transition metal complexes formed from a benzothiazole-based azo ligand. Bulletin of the Chemical Society of Ethiopia, 37(4), 931–944. https://doi.org/10.4314/bcse.v37i4.10
3. Amin, S., & Parle, A. (2018). Synthesis, characterization and anti-oxidant activity of 2-aryl benzothiazole derivatives International Journal of Current Pharmaceutical Research, 10(5), 3. https://doi.org/10.22159/ijcpr.2018v10i5.29685
4. Bahsis, L., Hrimla, M., Ayouchia, H. B. E., Anane, H., Julve, M., and Stiriba, S. (2020). 2-Aminobenzothiazole-Containing Copper(II) complex as catalyst in Click chemistry: an Experimental and Theoretical study. Catalysts, 10(7), 776. https://doi.org/10.3390/catal10070776
5. Ceramella, J., Iacopetta, D., Catalano, A., Cirillo, F., Lappano, R., and Sinicropi, M. S. (2022). A review on the antimicrobial activity of Schiff bases: data collection and recent studies. Antibiotics, 11(2), 191. https://doi.org/10.3390/antibiotics11020191
6. Gopichand, K., Mahipal, V., Rao, N. N., Ganai, A., and Rao, P. V. (2023b). Co(II), Ni(II), Cu(II), and Zn(II) complexes with Benzothiazole Schiff base ligand: Preparation, Spectral Characterization, DNA Binding, and In Vitro Cytotoxic Activities. Results in Chemistry, 5, 100868. https://doi.org/10.1016/j.rechem.2023.10086
7. Gul, Z., Din, N. U., Khan, E., Ullah, F., and Tahir, M. N. (2020). Synthesis, molecular structure, anti-microbial, anti-oxidant and enzyme inhibition activities of 2-amino-6-methylbenzothiazole and its Cu(II) and Ag(I) complexes. Journal of Molecular Structure, 1199, 126956. https://doi.org/10.1016/j.molstruc.2019.126956
8. Hasi, Q. M., Fan, Y., Yao, X. Q., Hu, D. C., and Liu, J. C. (2016). Synthesis, characterization, antioxidant and antimicrobial activities of a bidentate Schiff base ligand and its metal complexes. Polyhedron, 109, 75-80. https://doi.org/10.1016/j.poly.2016.01.052
9. Ismail, M. M. F., Abdulwahab, H. G., Nossier, E. S., Menofy, N. G. E., and Abdelkhalek, B. A. (2020). Synthesis of novel 2-aminobenzothiazole derivatives as potential antimicrobial agents with dual DNA gyrase/topoisomerase IV inhibition. Bioorganic Chemistry (Print), 94, 103437. https://doi.org/10.1016/j.bioorg.2019.103437
10. Jiang, J., Lei, Y., Ou, Y., Xu, L., Pi, Y., Yang, L., Li, Q., and Li, C. (2021). Synthesis, crystal structure, density functional theory calculations, and antimicrobial activity of silver(I) complex derived from 2‐aminobenzothiazole ligand. Applied Organometallic Chemistry, 35(6). https://doi.org/10.1002/aoc.6226
11. Kanagavalli, C., Sankarganesh, M., Dhaveethu, R., and Kalanithi, M. (2019). Spectral, NLO and antimicrobial studies of Co (II), Ni (II) and Cu (II) complexes of Schiff base ligands of 2-amino-6-nitrobenzothiazole. Journal of the Serbian Chemical Society, 84(3), 267–275. https://doi.org/10.2298/jsc180521101k
12. Khalil, M. I., and Khalal, Q. Z. (2021). Synthesis and characterization of new compounds derived from 2-hydrazinobenzothiazole and evaluated their antibacterial activity. Journal of Physics. Conference Series, 1853(1), 012007. https://doi.org/10.1088/1742-6596/1853/1/012007
13. Khan, M.A., Rahman, A.A. and Islam, S. (2013). A comparative study on the antioxidant activity of methanolic extracts from different parts of Morus alba L. (Moraceae). BMC Res Notes 6, 24 (2013). https://doi.org/10.1186/1756-0500-6-24
14. Kyhoiesh, H. a. K., and Al-Adilee, K. J. (2021). Synthesis, spectral characterization, antimicrobial evaluation studies and cytotoxic activity of some transition metal complexes with tridentate (N, N, O) donor azo dye ligand. Results in Chemistry, 3, 100245. https://doi.org/10.1016/j.rechem.2021.100245
15. Kyhoiesh, H. a. K., and Al-Adilee, K. J. (2023). Pt(IV) and Au(III) complexes with tridentate-benzothiazole based ligand: synthesis, characterization, biological applications (antibacterial, antifungal, antioxidant, anticancer and molecular docking) and DFT calculation. Inorganic Chemica Acta/Inorganic Chemica Acta, 555, 121598. https://doi.org/10.1016/j.ica.2023.121598
16. Lemilemu, F., Bitew, M., Demissie, T. B., Eswaramoorthy, R., and Endale, M. (2021). Synthesis, antibacterial and antioxidant activities of Thiazole-based Schiff base derivatives: a combined experimental and computational study. BMC Chemistry, 15(1). https://doi.org/10.1186/s13065-021-00791-w
17. Mahmood, W. a. R., Aldabbagh, A. K. A., and Mahmoud, M. A. (2022). Synthesis and characterization of new benzothiazole-derived Schiff bases metal complexes. Mağallaẗ Baġdād Li-l-ʿulūm, 19(2), 0378. https://doi.org/10.21123/bsj.2022.19.2.0378
18. Mishra, N., Gound, S. S., Mondal, R., Yadav, R., and Pandey, R. (2019b). Synthesis, characterization and antimicrobial activities of benzothiazole-imino-benzoic acid ligands and their Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) complexes. Results in Chemistry, 1, 100006. https://doi.org/10.1016/j.rechem.2019.100006
19. Omaka, O. N., Ekennia, A. C., Njoku, N. N., and Onwudiwe, D. C. (2018b). Nickel(II) and copper(II) complexes of 2,2’‐bibenzo[d]thiazole: Synthesis, characterisation and biological studies. Applied Organometallic Chemistry, 32(4). https://doi.org/10.1002/aoc.4241
20. Reygaert, W. (2018). An overview of the antimicrobial resistance mechanisms of bacteria. AIMS Microbiology, 4(3), 482–501. https://doi.org/10.3934/microbiol.2018.3.482
21. Shah, S. S., Shah, D., Khan, I., Ahmad, S., Ali, U., and Rahman, A. (2020). Synthesis and antioxidant activities of Schiff bases and their complexes: An updated review. Biointerface Res. Appl. Chem, 10(6), 6936-6963. https://doi.org/10.33263/BRIAC106.69366963
22. Sharma, P. C., Sinhmar, A., Sharma, A., Rajak, H., & Pathak, D. P. (2012). Medicinal significance of benzothiazole scaffold: an insight view. Journal of Enzyme Inhibition and Medicinal Chemistry, 28(2), 240–266. https://doi.org/10.3109/14756366.2012.720572
23. Sunjuk, M., Al-Najjar, L., Shtaiwi, M., El‐Eswed, B., Al-Noaimi, M., Al‐Essa, L. Y., and Sweidan, K. (2022b). Transition Metal Complexes of Schiff Base Ligands Prepared from Reaction of Aminobenzothiazole with Benzaldehydes. Inorganics, 10(4), 43. https://doi.org/10.3390/inorganics10040043
24. Sunjuk, M., Al-Najjar, L., Shtaiwi, M., El‐Eswed, B., Al-Noaimi, M., Al‐Essa, L. Y., and Sweidan, K. (2022). Transition Metal Complexes of Schiff Base Ligands Prepared from Reaction of Aminobenzothiazole with Benzaldehydes. Inorganics (Basel), 10(4), 43. https://doi.org/10.3390/inorganics10040043
25. Wang, L., Shaalan, N., Lafta, A. K., and Akeedi, J. M. A. (2024). Preparation, Characterization, and Biological Activity of La(III), Nd(III), Er(III), Gd(III), and Dy(III) Complexes with Schiff Base Resulted from Reaction of 4-Antipyrinecarboxaldehyde and 2-Aminobenzothiazole. Indonesian Journal of Chemistry, 24(2), 358. https://doi.org/10.22146/ijc.8726
26. Yadav, K. P., Rahman, M., Nishad, S., Maurya, S. K., Anas, M., & Mujahid, M. (2023). Synthesis and biological activities of benzothiazole derivatives: A review. Intelligent Pharmacy, 1(3), 122–132. https://doi.org/10.1016/j.ipha.2023.06.001
27. Zheng, X., Li, C., Cui, M., Song, Z., Bai, X., Liang, C., Wang, H., and Zhang, T. (2020). Synthesis, biological evaluation of benzothiazole derivatives bearing a 1, 3, 4-oxadiazole moiety as potential anti-oxidant and anti-inflammatory agents. Bioorganic &MedicinalChemistryLetters,30(13),127237. https://doi.org/10.1016/ j.bmcl.2020.127237
Published
2024-06-25
How to Cite
Minakshi Kumari, Priya Saini, Mohd Hussain, Mamta Khatak, Bhoj Raj, Sudhir Kaushik, Sudhir Kaushik, & Mahesh Kumar. (2024). Synthesis And In Vitro Biological Evaluation Of Metal Complexes Of 2-Aminobenzothiazole. Revista Electronica De Veterinaria, 25(1S), 5-11. Retrieved from https://veterinaria.org/index.php/REDVET/article/view/565
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