2-Aminobenzotiyazol Türevlerinin Metal Komplekslerinin Antimikrobiyal Aktivite Çalışmaları

Öz

2-Aminobenzotiyazol ve türevlerinin genel olarak, ilaç keşfi uygulamaları, diyabet tedavilerin geliştirilmesi, epilepsi, amyotrofik lateral skleroz, analjezi, tüberküloz tedavisi ve virüs enfeksiyon uygulamaları vardır. Bu çalışmada, 2-aminobenzotiyazol (1), 2-amino-6-klorobenzotiyazol (6), 2-amino-6-metilbenzotiyazol (11) ve 2-amino-6-metoksibenzotiyazolün (16) Fe(III) (2, 7, 12, 17), Co(II) (3, 8, 13, 18), Ni(II) (4, 9, 14, 19) ve Cu(II) (5, 10, 15, 20) kompleksleri, literatürde bulunan yöntemle sentezlenmiştir. Sentezlenen kompleks bileşiklerin (1-20) yapıları, Atomik Absorpsiyon Spektroskopisi (AAS) uygulanarak önerilmiştir. Ayrıca, 1-20'nin antimikrobiyal özellikleri Candida albicans'a (antifungal aktivite) ve Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus, Listeria monocytogenes, and Enterococcus faecalis’e (antibakteriyel aktivite) karşı da test edilmiştir. Sonuçlar, kontrol bileşikleri Flukonazol ve Ketokonazol (antifungal aktivite) ve Vankomisin, Levofloksasin, Sefepim ve Kloramfenikol (antibakteriyel aktivite) kullanılarak elde edilen sonuçlarla karşılaştırılmıştır. Aktivite çalışmaları sonucunda, sentezlenen bileşikler bakteri ve mayalara karşı aktivite göstermiştir. En iyi aktivite sonuçları C. albicans mayasında 6 ve 10 nolu bileşiklerde, S. aureus bakterisinde 20 nolu bileşikte, E. faecalis bakterisinde 13 nolu bileşikte, B. subtilis bakterisinde 12, 13, 17 ve 20 nolu bileşiklerde, P. aeruginosa bakterisinde 5 ve 19 nolu bileşiklerde, E. coli bakterisinde 1, 4, 6, 9, 17 ve 20 nolu bileşiklerde ve L. monocytogenes bakterisinde 5, 6, 8, 17 ve 19 nolu bileşiklerde gözlemlenmiştir. Özellikle E. coli için 4 numaralı, C. albicans için 6 numaralı ve 10 numaralı bileşikler kontrol bileşiklerinden daha iyi aktivite göstermiştir.

Anahtar Kelimeler

• 2-Aminobenzotiyazol
• metal kompleksi
• antibakteriyel aktivite
• antifungal aktivite

Proje Numarası

2022–03

Antimicrobial Activity Studies of Metal Complexes of 2-Aminobenzothiazole Derivatives

Öz

2-Aminobenzothiazole and its derivatives generally have applications in drug discovery, development of diabetes treatments, epilepsy, amyotrophic lateral sclerosis, analgesia, tuberculosis treatment, and viral infections. In this study, Fe(III) (2, 7, 12, 17), Co(II) (3, 8, 13, 18), Ni(II) (4, 9, 14, 19), and Cu(II) (5, 10, 15, 20) complexes of 2-aminobenzothiazole (1), 2-amino-6-chlorobenzothiazole (6), 2-amino-6-methylbenzothiazole (11), and 2-amino-6-methoxybenzothiazole (16), respectively, were synthesized by the method found in the literature. The architectures of the synthesized complex compounds (1-20) were postulated through the application of Atomic Absorption Spectroscopy (AAS). Furthermore, the antimicrobial activities of compounds 1–20 were tested against Candida albicans (antifungal activity) and Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus, Listeria monocytogenes, and Enterococcus faecalis (antibacterial activity). The results were compared with those obtained using the control compounds Fluconazole and Ketoconazole (antifungal activity) and Vancomycin, Levofloxacin, Cefepime, and Chloramphenicol (antibacterial activity). As a result of activity studies, synthesized compounds show activity against bacteria and yeasts. The best activity results were observed compounds 6 and 10 in C. albicans yeast, compound 20 in S. aureus bacteria, compound 13 in E. faecalis bacteria, compounds 12, 13, 17, and 20 in B. subtilis bacteria, compounds 5 and 19 in P. aeruginosa bacteria, compounds 1, 4, 6, 9, 17, and 20 in E. coli bacteria, and compounds 5, 6, 8, 17, and 19 in in L. monocytogenes bacteria. In particular, compound 4 for E. Coli, 6, and 10 for C. albicans showed better activity than the control compounds.

Anahtar Kelimeler

• 2-Aminobenzothiazole
• metal complex
• antibacterial activity
• antifungal activity

Destekleyen Kurum

This study was prepared by the Kütahya Dumlupınar University Scientific Research Projects Committee using materials from project number 2022/03.

Proje Numarası

2022–03

Etik Beyan

This study does not require ethics committee approval or any special permissions.

Teşekkür

We would like to thank the Kütahya Dumlupınar University Scientific Reserch Projects Committee for their contributions.

Kaynakça

1. Bhoi, M. N., Borad, M. A., & Patel, H. D. (2014). Synthetic strategies for fused benzothiazoles: past, present, and future. Synthetic Communications, 44(17), 2427-2457. https://doi.org/10.1080/00397911.2014.907426
2. Maurya, R. C., & Mishra, D. D. (1990). Synthesis and physicochemical studies of some mixed-ligand cyanonitrosyl {CrNO}5 hetero complexes of chromium(I) involving benzothiazole and related ligands. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 20(7), 865-874. https://doi.org/10.1080/00945719008048180
3. Abdel-Hady, A. E. M. (2014). Inner-sphere oxidation of 2-aminobenzothiazole chromium(III) complex by periodate. Evidence for the inhibiting effect of copper(II) and iron(II) ions. Industrial & Engineering Chemistry Research, 53(15), 6268-6273. https://doi.org/10.1021/ie5001168
4. Giusti, A., Giliberti, E., & Peyronel, G. (1984). Chromium(III) complexes of 2-aminobenzothiazole. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 40A(3), 275-277.
5. Campbell, M. J. M., Grzeskowiak, R., & Juneja, G. S. (1978). Some iron(III) complexes of 2-aminobenzothiazole. Journal of Inorganic and Nuclear Chemistry, 40(6), 1247-1249. https://doi.org/10.1016/0022-1902(78)80547-8
6. Trzesowska-Kruszynska, A. (2011). Iron(III) complexes with 2-aminobenzothiazole: compounds governed by non-covalent interactions. Journal of Coordination Chemistry, 64(4), 663-678. https://doi.org/10.1080/00958972.2011.553223
7. Campbell, M. J. M., Card, D. W., & Grzeskowiak, R., (1969) Cobalt(II) and nickel(II) halide complexes of 2-aminobenzothiazole. Inorganic and Nuclear Chemistry Letters, 5(1), 39-43. https://doi.org/10.1016/0020-1650(69)80234-5
8. Duff, E. J., Hughes, M. N., & Rutt, K. J. (1969). Complexes of thiazoles. II. Complexes of 2-amino-, 2-chloro-, and 2-methylbenzothiazole with cobalt(II), nickel(II), copper(II), and zinc(II) salts. Journal of the Chemical Society A: Inorganic, Physical, Theoretical, 14, 2101-2105. https://doi.org/10.1039/J19690002101

9. Bati, H., Saracoglu, H., Caliskan, N., & Soylu, S. (2005). Diacetatobis(2-aminobenzothiazole-κN)cobalt(II). Acta Crystallographica Section C, Structural Chemistry, C61(7), m342-m343. https://doi.org/10.1107/S0108270105016811
10. Bati, H., Saracoglu, H., Caliskan, N., & Buyukgungor, O. (2006). Bis(2-aminobenzothiazole-κN)dichlorocobalt(II). Acta Crystallographica Section E, Crystallographic Communications, E62(9), m2313-m2315. https://doi.org/10.1107/S1600536806033496
11. Kadirova, S. A., Tursunova, M. R., Ishankhodzhaeva, M. M., Parpiev, N. A., Karimov, Z., Tozhiboev, A., & Tashkhodzhaev, B. (2007). Synthesis and structure of complexes of Co(II) acetate and Zn(II) chloride with 2-aminobenzothiazole. Russian Journal of General Chemistry, 77(10), 1807-1810. https://doi.org/10.1134/S1070363207100234
12. Aly, A. A. M., El-Meligy, M. S., Zidan, A. S., & El-Shabasy, M. (1990). Thiazoles as complexing agents towards transition metal haloacetates: spectral, magnetic and thermal properties. Anales de Quimica, 86(1), 19-23.
13. Campbell, M. J. M., Card, D. W., Grzeskowiak, R., & Goldstein, M. (1970). Complexes of 2-aminobenzothiazole with cobalt(II) and nickel(II). Journal of the Chemical Society A: Inorganic, Physical, Theoretical, 4, 672-675.
14. Matsichek, I., Davarska, G., & Davarski, K. (1987). The structure of bis(2-aminobenzothiazole)dichlorocobalt(II). Zeitschrift für Kristallographie - New Crystal Structures, 180(1-4), 157-164.
15. Dojer, B., Pevec, A., Breznik, K., Jaglicic, Z., Gyergyek, S., & Kristl, M. (2019). Structural and thermal properties of new copper and nickel single-source precursors. Journal of Molecular Structure, 1194, 171-177. https://doi.org/10.1016/j.molstruc.2019.05.047
16. Maurya, R. C., Sharma, P., & Sutradhar, D. (2003). Metal thiocyanato complexes: Synthesis, magnetic, and spectral studies of some mixed-ligand thiocyanato complexes of nickel(II) involving benzothiazole and benzimidazole derivatives. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 33(3), 387-401. https://doi.org/10.1081/SIM-120019992
17. Singh, P. P., Pathak, L. P., & Srivastava, S. K. (1980). Application of quantitative values of softness on the elucidation of structure of bimetallic complexes. II. Journal of Inorganic and Nuclear Chemistry, 42(4), 533-539. https://doi.org/10.1016/0022-1902(80)80081-9
18. Giusti, A., Peyronel, G., & Giliberti, E. (1982). Copper(I) and silver(I) complexes of 2-aminobenzothiazole. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 38A(11), 1185-1187.
19. Garnovskii, D. A., Antsyshkina, A. S., Sadimenko, A. P., Porai-Koshits, M. A., Osipov, O. A., & Garnovskii, A. D. (1987). On the reasons of decrease of primary NH2-group stretching frequencies in the adducts of Lewis acid with 2-aminoheterocycles. Doklady Akademii Nauk SSSR, 296(5), 1119-11121.
20. Desseyn, H. O., Slootmaekers, B., Perlepes, S. P., & Fabretti, A. C. (1989). The vibrational spectra and force constants of the planar tetrachlorocuprate(2-) ion in bis(2-aminobenzothiazolium) tetrachlorocuprate(II). Inorganica Chimica Acta, 156(1), 113-117. https://doi.org/10.1016/S0020-1693(00)90376-1
21. Antolini, L., Benedetti, A., Fabretti, A. C., & Giusti, A. (1988). Crystal structure and electronic and EPR spectra of a compound containing a symmetric square-planar tetrachlorocuprate(2-) ion. Inorganic Chemistry, 27(12), 2192-2194. https://doi.org/10.1021/ic00285a036
22. Satyanarayana, D., & Mohapatra, B. K. (1975). Complexes of copper(II) acetate with nitrogen donors. Indian Journal of Chemistry, 13(2), 185-186.
23. Maniukiewicz, W. (2004). trans-Bis(2-amino-1,3-benzothiazole-κN3)dichlorocopper(II). Acta Crystallographica Section E, Crystallographic Communications, E60(3), m340-m341. https://doi.org/10.1107/S1600536804003885
24. Sun, Y. F., Jing, R. L., & Zheng, Z. B. (2007) Tetra-μ-acetato-κ8O:O'-bis[(2-amino-1,3-benzothiazole-κN) copper(II)] butanol disolvate. Acta Crystallographica Section E, Crystallographic Communications, E63(7), m1881-m1881. https://doi.org/10.1107/S1600536807027948
25. Ma, W., Qian, B., Cheng, Q., Wang, J., Xu, X., Lu, L., Yang, X., Wang, X., & Song, H. (2006). Synthesis, crystal structure and spectral characterization of the complex [Zn(CH3COO)2(C7H6N2S)2]. Reng Jing Xuebao, 35(5), 1061-1065.
26. Suh, S. W., Kim, C. H., & Kim, I. H. (2009). Bis(2-aminobenzothiazole-κN1)bis(thiocyanato-κN)zinc(II). Acta Crystallographica Section E, Crystallographic Communications, E65(9), m1054. https://doi.org/10.1107/S1600536809030931
27. Zehra, S., Tabassum, S., Al-Lohedan, H. A., & Arjmand, F. (2018). A zwitterionic Zn(II) benzothiazole nanohybrid conjugate as hydrolytic DNA cleavage agent. Inorganic Chemistry Communications, 93, 69-72. https://doi.org/10.1016/j.inoche.2018.05.008
28. Kefi, R., Jeanneau, E., Lefebvre, F., & Ben Nasr, C. (2011). Bis(2-amino-1,3-benzothiazol-3-ium) tetrachloridozincate(II). Acta Crystallographica Section E, Crystallographic Communications, E67(6), m654-m655. https://doi.org/10.1107/S1600536811015753
29. Kim, Y. I. (2012). Bis(2-amino-1,3-benzothiazole-κN)dichloridozinc(II) ethanol hemisolvate. Acta Crystallographica Section E, Crystallographic Communications, E68(2), m178-m179. https://doi.org/10.1107/S1600536812001560
30. Vasilev, G., & Davarski, K. (1985). Synthesis, chemical structure and biological activity of some zinc complexes of aminothiazole and aminobenzothiazoles. Doklady Bolgarskoi Akademii Nauk, 38(8), 1057-1060.
31. Yan, X., Fan, Y., Bi, C., Zhang, X., Zuo, J., Zhang, P., & Zhang, Z. (2014). Synthesis, crystal structure, and theoretical calculation of the Cd(II) complex with 2-aminobenzothiazole. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 44(4), 603-610. https://doi.org/10.1080/15533174.2013.783860
32. Giusti, A., & Peyronel, G. (1982). Zinc(II), cadmium(II), and mercury(II) complexes of 2-aminobenzothiazole. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 38A(9), 975-979.
33. Dash, R. N., & Rao, D. V. R. (1974). Complexes of benzothiazole and 2-substituted benzothiazoles with silver(I). Coordination number 2 and 3. Journal of the Indian Chemical Society, 51(9), 787-789.
34. Tewari, S. P., Tripathi, P., & Sinha, A. I. P. (1991). Silver(I) complexes of 2-thiazolamine and 2-benzothiazolamines. Asian Journal of Chemistry, 3(2), 124-127.
35. Jiang, J. H., Lei, Y. H., Ou, Y. H., Li, X., Pi, Y. Y., Ye, L. J., Li, Q. G., & Li, C. H. (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), e6226. https://doi.org/10.1002/aoc.6226
36. Strasser, C. E., de Jongh, L. A., Cronje, S., & Raubenheimer, H. G. (2009). Bis(1,3-benzothiazol-2-amine-κN3)silver(I) nitrate acetone solvate. Acta Crystallographica Section E, Crystallographic Communications, E65(3), m265-m266. https://doi.org/10.1107/S1600536809004176
37. Chen, Z. F., Zhang, M., Shi, S. M., Huang, L., Liang, H., Xu, Q., & Yu, K. B. (2005) Synthesis, crystal structure and antibacterial activity of 2-aminobenzotiazole silver(I) nitrate. Yingyong Huaxue, 22(7), 730-733.
38. Giusti, A., Peyronel, G., & Giliberti, E. (1982). Antimony(III) and bismuth(III) trihalide complexes of 2-aminobenzothiazole. Polyhedron, 1(7-8), 655-658. https://doi.org/10.1016/S0277-5387(00)80863-3
39. Nardelli, M., Pelizzi, C., & Pelizzi, G. (1975). Tin complexes containing the nitrate group. Crystal structure of polymeric (2-aminobenzothiazolato) nitratotin(II). Journal of the Chemical Society, Dalton Transactions, 15, 1595-1597. https://doi.org/10.1039/DT9750001595
40. Pelizzi, C., Pelizzi, G., & Tarasconi, P. (1980). Synthesis and reactivity of organotin(IV) nitrates with heterocyclic systems. Inorganica Chimica Acta, 40(2), 183-186. https://doi.org/10.1016/S0020-1693(00)92001-2
41. Ouchi, A., Takeuchi, T., & Taminaga, I. (1970). The syntheses and properties of the benzothiazole or benzimidazole derivative adducts of tin(II, IV) and antimony(III) halides. Bulletin of the Chemical Society of Japan, 43(9), 2840-2844. https://doi.org/10.1246/bcsj.43.2840
42. Surpina, L. V., Garnovskii, A. D., Kolodyazhnyi, Y. V., & Osipov, O. A. (1971). Complexes of niobium pentachloride with azoles. Zhurnal Obsh Khimii, 41(10), 2279-2283.
43. Lynch, D. E., & Duckhouse, H. L. (2001). trans-Bis(2-amino-6-nitro-1,3-benzothiazole-N)dichloroplatinum(II) tetrakis(N,N'-dimethylformamide) solvate and tetrakis(2-amino-5-methyl-1,3,4-thiadiazole-N4)platinum(II) hexachloroplatinate(IV) bis(N,N'-dimethylformamide) solvate. Acta Crystallographica Section C, Structural Chemistry, C57(9), 1036-1038. https://doi.org/10.1107/s0108270101009933
44. Berdan, I., & Calu, N. (1981). Complex compounds of thallium(III) with heterocyclic organic ligands. II. UV and visible absorption spectra. Buletinul Institutului Politehnic din Iași Secția Chimie și Inginerie Chimică, 27(1-2), 9-14.
45. Berdan, I. (1980). Complex combinations of thallium(III) with organic heterocyclic ligands. I. Synthesis and some properties. Buletinul Institutului Politehnic din Iași Secția Chimie și Inginerie Chimică, 26(3-4), 21-26.
46. Wang, E. C., Li, J., Li, Y. L., Yang, E. C., & Zhao, X. J. (2011). Three 2-aminobenzothiazole-based mercury complexes tuned by competitive coordination between the coligands: synthesis, structures, and fluorescent properties. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 41(7), 791-797. https://doi.org/10.1080/15533174.2011.591305
47. Rossi, R., Duatti, A., Magon, L., Marchi, A., Medici, A., Fogagnolo, M., Casellato, U., & Graziani, R. (1985). Synthesis, reactivity and x-ray crystal structures of mixed thiazolato- or carboxylatocarbonyl(phosphine)rhenium(I) complexes. Transition Metal Chemistry, 10(11), 413-416. https://doi.org/10.1007/bf01096747
48. Baghlaf, A. O., Banaser, K., Hashem, H. Y., Bishry, A. A., & Ishaq, M. (1994). Synthesis and spectroscopic studies on some ruthenium(II) complexes. Qatar University Science Journal, 14(Spec. Issue), 75-79. http://hdl.handle.net/10576/9874
49. Baghlaf, A. O., Ishaq, M., Rahman, S. A., Al-Tahir, A. B., Zaidan, A., & Kabli, R. A. (1988). Synthesis and characterization of dichlorodicarbonylruthenium(II) complexes of naphthisoxazole and other donor ligands. Polyhedron, 7(3), 219-221. https://doi.org/10.1016/S0277-5387(00)80554-9
50. Maurya, R. C., Verma, R., & Shukla, B. (1999). Coordination chemistry of dioxotungsten(VI), synthesis and characterization of some isothiocyanato complexes of dioxotungsten(VI) with biologically active chelating molecules. Indian Journal of Chemistry. Section A, Inorganic, Bio-İnorganic, Physical, Theoretical & Analytical Chemistry, 38A(7), 730-735.
51. Mikherdov, A. S., Baikov, S. V., Proskurina, I. K., Shetnev, A. A., & Kotov, A. D. (2019). Synthesis and properties of C,N-chelated carbene complexes of palladium(II) with 2-aminobenzo[d]thiazole fragment. Russian Journal of General Chemistry, 89(10), 2062-2068. https://doi.org/10.1134/S1070363219100128
52. Al-Jibori, S. A., Habeeb, A. T., Al-Jibori, G. H. H., Dayaaf, N. A., Merzweiler, K., Wagner, C., Schmidt, H., & Hogarth, G. (2014). Palladium(II) saccharinate (sac) and thiosaccharinate (tsac) complexes with supporting amino- and acetylamino-thiazole ligands: Crystal structures of trans-[PdCl2(abzt)2].dmf (abzt = 2-aminobenzothiazole), trans-[PdCl2(bzta)2].dmf (bzta = 2-acetylaminobenzothiazole) and trans-[Pd(sac)2(abzt)2].2dmf. Polyhedron, 67, 338-343. https://doi.org/10.1016/j.poly.2013.09.007
53. Shabana, A. A., Butler, I. S., Gilson, D. F. R., Jean-Claude, B. J., Mouhri, Z. S., Mostafa, M. M., & Mostafa, S. I. (2014). Synthesis, characterization, anticancer activity and DNA interaction studies of new 2-aminobenzothiazole complexes; crystal structure and DFT calculations of [Ag(Habt)2]ClO4. Inorganica Chimica Acta, 423(Part_B), 242-255. https://doi.org/10.1016/j.ica.2014.09.018
54. Misra, R., Mahapatra, B. B., & Guru, S. (1981). Cobalt(II) and copper(II) complexes with substituted aminobenzothiazoles. Part II. Journal of the Indian Chemical Society, 58(8), 808-810.
55. Misra, R., & Guru, S. (1982). Nickel(II) complexes with substituted amino benzothiazoles. Journal of the Indian Chemical Society, 59(8), 987-988.
56. Misra, R., Mohapatra, B. B., & Guru, S. (1979). Mercury(II) complexes with substituted aminobenzothiazoles. Journal of the Indian Chemical Society, 56(8), 832-833.
57. Stojkovic, D. L., Avdovic, E. H., Djukic, M. B., Jevtic, V. V., Petrovic, D. S., Jelic, R. M., Jurisevic, M., Gajovic, N., Markovic, V., Arsenijevic, A., Jovanović, I., Radojević, I. D., & Milić, S. S. J. (2025). Synthesis, comprehensive characterization and investigation of biological properties of newly synthesized Pt(II)-aminothiazole complexes: Combining experimental and computational approach. Journal of Organometallic Chemistry, 1023, 123411. https://doi.org/10.1016/j.jorganchem.2024.123411
58. Jovicic Milic, S. S., Jevtic, V. V., Radisavljevic, S. R., Petrovic, B. V., Radojevic, I. D., Rakovic, I. R., Petrovic, D. S., Stojkovic, D. L., Jurisevic, M., Gajovic, N., Petrović, A., Arsenijević, N., Jovanović, I., Klisurić, O. R., Vuković, N. L., Vukić, M., & Kačániová, M. (2022). Synthesis, characterization, DNA interactions and biological activity of new palladium(II) complexes with some derivatives of 2-aminothiazoles. Journal of Inorganic Biochemistry, 233, 111857. https://doi.org/10.1016/j.jinorgbio.2022.111857
59. Kirubavathy, S. J., Velmurugan, R., Karvembu, R., Bhuvanesh, N. S. P., Enoch, I. V. M. V., Selvakumar, P. M., & Chitra, S. (2016). Co(II) complex of 2-amino-6-methylbenzothiazole: synthesis, structure and biological evaluation. Indian Journal of Chemistry. Section A, Inorganic, Bio-Inorganic, Physical, Theoretical & Analytical Chemistry, 55A(11), 1297-1304.
60. Gul, Z., Ud Din, N., Khan, E., Ullah, F., & Nawaz Tahir, M. (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
61. Chaurasia, M. R., Shukla, P., & Singh, N. K. (1982). Transition metal complexes of 6-methyl-2-aminobenzothiazole-Part III. Defence Science Journal, 32(2), 75-79. https://doi.org/10.5281/zenodo.6345739
62. Chaurasia, M. R., Shukla, P., & Singh, N. K. (1982). Synthesis and structural studies of 6-methyl-2-aminobenzothiazole with transition metal ions. Indian Journal of Natural Sciences, 2(A), 1-5.
63. Chaurasia, M. R., & Shukla, P. (1983). Synthesis and structural studies of metal complexes of 6-methyl-2-aminobenzothiazole and 2-methylbenzimidazole. Journal of the Indian Chemical Society, 60(11), 1011-1013.
64. Kirubavathy, S. J., Velmurugan, R., Karvembu, R., Bhuvanesh, N. S. P., Enoch, I. V. M. V., Selvakumar, P. M., & Chitra, S. (2016). Co(II) complex of 2-amino-6-methylbenzothiazole: Synthesis, structure and biological evaluation. Indian Journal of Chemistry, 55A:1297-1304.
65. Saraswat, K., & Kant, R. (2013). Synthesis, characterization, and biological activity of some molybdenum(VI) complexes. Der Pharma Chemica, 5(4), 347-356.
66. Lozano, R., Roman, J., Ragel, V., & Ramirez, M. C. (1989). Oxychloride molybdenum(V) complexes with benzothiazoles. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 19(2), 125-135. https://doi.org/10.1080/00945718908048057
67. Sinha, A. I., Agarwal, P., & Tewari, S. (1989). Metal complexes of 6-methoxy-2-benzothiazolamine. Current Science, 58(16), 899-903. https://www.jstor.org/stable/24092836
68. Craciunescu, D. G., Doadrio Lopez, A., Molina, C., Gomez, A., Sanchez de Leon, M. S., Fernandez de Simon, L., Ghirvu, C., & Gaston de Iriarte, E. (1987). Structure-antitumor and antitrypanosomal activities relations for the platinum(L)2(I)2(OH)2 complexes, where L is a thiazole or sulfonamide derivative. Anales de la Real Academia Nacional de Farmacia, 53(1), 5-27.
69. Kaplancıklı, Z. A., Turan-Zitouni, G., Özdemir, A., Revial, G., & Güven, K. (2007) Synthesis and antimicrobial activity of some thiazolyl-pyrazoline derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 182(4), 749-764. https://doi.org/10.1080/10426500601047529
70. Avan, İ., Güven, A., & Güven, K. (2013) Synthesis and antimicrobial investigation of some 5H-pyridazino[4,5-b] indoles. Turkish Journal of Chemistry, 37, 271-291. https://doi.org/10.3906/kim-1210-22
71. İlkimen, H., Yenikaya, C., Gülbandılar, A., & Sarı, M. (2016). Synthesis and characterization of a novel proton salt of 2-amino-6-nitrobenzothiazole with 2,6-pyridinedicarboxylic acid and its metal complexes and their antimicrobial and antifungal activity studies. Journal of Molecular Structure, 1120, 25-33. https://doi.org/10.1016/j.molstruc.2016.04.068
72. Abo-Rehab, R. S., Kasim, E. A., Farhan, N., Tolba, M. S., Shehata, M. R., & Abdalla, E. M. (2024). Synthesis, characterization, anticancer, antibacterial, antioxidant, DFT, and molecular docking of novel La (III), Ce (III), Nd (III), and Dy (III) lanthanide complexes with Schiff base derived from 2-aminobenzothiazole and coumarin. Applied Organometallic Chemistry, 38(9), e7622. https://doi.org/10.1002/aoc.7622
73. Moreira, J. M., Vieira, S. S. F., Correia, G. D., de Almeida, L. N., Finoto, S., Brandl, C. A., Msumange, A. A., Galvao, F., Pires de Oliveira, K. M., Caneppele Paveglio, G., da Silva, M. M., Tirloni, B., de Carvalho, C. T., & Roman, D. (2025). Synthesis and characterization of novel hydrazone complexes: exploring DNA/BSA binding and antimicrobial potential. ACS Omega, 10(7), 7428-7440. https://doi.org/10.1021/acsomega.5c00069
74. Chaitanya, M. S., Nagendrappa, G., & Vaidya, V. P. (2010). Synthesis, biological and pharmacological activities of 2-methyl-4Hpyrimido[2,1-b][1,3]benzothiazoles. Journal of Chemical and Pharmaceutical Research, 2(3), 206-213.
75. Song, S., Song, M., Zhang, H., & Yang, L. (2010). Crystal structure and antibacterial activity of 2-aminobenzothiazole complexes. Huaxue Yanjiu, 21(6), 21-25.
76. Tweedy, B. G. (1964). Plant extracts with metal ions as potential antimicrobial agents. Phytopatology, 55, 910-914.
77. Chohan, Z. H., Arif, M., Akhtar, M. A., & Supuran, C. (2006). Metal-based antibacterial and antifungal agents: synthesis, characterization, and in vitro biological evaluation of Co(II), Cu(II), Ni(II), and Zn(II) complexes with amino acid-derived compounds. Bioinorganic Chemistry and Applications, 2006, 83131. https://doi.org/10.1155/BCA/2006/83131
78. Raman, N., Raja, S. J., & Sakthivel, A. (2009). Transition metal complexes with Schiff-base ligands: 4-aminoantipyrine based derivatives- A review. Journal of Coordination Chemistry, 62(5), 691-709. https://doi.org/10.1080/00958970802326179