4-Nitro-N-(6-sülfamoilbenzotiazol-2-il)benzamidin Metal Komplekslerinin Sentezi ve Karakterizasyonu

Yıl 2025, Cilt: 5 Sayı: 2, 38 - 44, 28.11.2025

Halil İlkimen , Cengiz Yenikaya , Aysel Gülbandılar

https://doi.org/10.62425/atakim.1678727

Öz

Bu çalışmada, 4-nitro-N-(6-sülfamoilbenzotiazol-2-il)benzamidin (abt) yeni Fe(II) {[Fe(abt)2(SO4)].H2O (1)}, Ni(II) {[Ni(abt)2(Ac)2].4H2O (2)} ve Cu(II) {[Cu(abt)2(Ac)2].4H2O (3)} kompleksleri sentezlendi. 1-3’ün yapıları, element analizi, AAS, molar iletkenlik ve manyetik duyarlılık yöntemleri ile önerildi. Spektroskopik değerlendirmenin bir sonucu olarak, 1-3 bileşiklerinin iyonik olmayan ve tetrahedral bir konformasyon sergilediği belirlendi. Tüm maddelerin C. albicans (maya), E. faecalis, E. coli, L. monocytogenes, S. aureus, P. aeruginosa ve B. subtilis (bakteri) duyarlılığına ilişkin kapsamlı bir inceleme yürütüldü ve kapsamlı bir şekilde araştırıldı. Antimikrobiyal aktiviteler Ketokonazol, Flukonazol, Levofloksasin, Kloramfenikol, Vankomisin ve Sefepim ile karşılaştırıldı. Bileşikler abt ve 2, S. aureus ve B. subtilis bakterilerinde daha iyi aktivite gösterirken, bileşikler 1-3, E. coli ve E. faecalis bakterilerinde ve C. albicans mayasında aynı aktiviteyi gösterdi. Kompleks 3, L. monocytogenes bakterilerinde daha iyi aktivite gösterdi.

Anahtar Kelimeler

4-Nitro-N-(6-sülfamoilbenzotiazol-2-il)benzamid , metal kompleksi , tetrahedral kompleks , antimikrobiyal aktivite.

Synthesis and Characterization of Metal Complexes of 4-Nitro-N-(6-sulfamoylbenzothiazol-2-yl)benzamide

Öz

In this study, the new Fe(II) {[Fe(abt)2(SO4)].H2O (1)}, Ni(II) {[Ni(abt)2(Ac)2].4H2O (2)} and Cu(II) {[Cu(abt)2(Ac)2].4H2O (3)} complexes of 4-nitro-N-(6-sulfamoylbenzothiazol-2-yl)benzamide (abt) were synthesized. The structures (1-3) were suggested by elemental analysis, AAS, molar conductivity, and magnetic susceptibility methods. As a consequence of spectroscopic evaluation, it was determined that compounds 1-3 exhibited a non-ionic and tetrahedral conformation. A comprehensive examination was conducted on the susceptibility of all substances to C. albicans (yeast), E. faecalis, E. coli, L. monocytogenes, S. aureus, P. aeruginosa, and B. subtilis (bacteria) were thoroughly investigated. The antimicrobial activities were contrasted with those of Ketoconazole, Fluconazole, Levofloxacin, Chloramphenicol, Vancomycin, and Cefepime. Compounds abt and 2 showed better activity in S. aureus and B. subtilis bacteria, while compounds 1-3 showed the same activity in E. coli and E. faecalis bacteria and C. albicans yeast. Complex 3 showed better activity in L. monocytogenes bacteria.

Anahtar Kelimeler

4-Nitro-N-(6-sulfamoylbenzothiazol-2-yl)benzamide , metal complex , tetrahedral complex , antimicrobial activity.

Teşekkür

The authors acknowledge the support provided by Kütahya Dumlupınar University Research Fund (grant No. 2024/16).

Kaynakça

• 1. Kovács E, Rózsa B, Csomos A, Csizmadia IG, Mucsi Z. Amide activation in ground and excited states. Molecules 2018;23(11):2859(1-31).
• 2. McIntosh JA, Donia MS, Schmidt EW. Ribosomal peptide natural products: bridging the ribosomal and nonribosomal worlds. Nat Prod Rep. 2009;26:537-559.
• 3. Tamura K. Ribosome evolution: emergence of peptide synthesis machinery. J Biosci. 2011;36(5):921-928.
• 4. Petchey MR, Grogan G.Enzyme-catalysed synthesis of secondary and tertiary amides. Adv Synth Catal. 2019;361(17):3895-3914.
• 5. Ovung A, Bhattacharyya J. Sulfonamide drugs: structure, antibacterial property, toxicity, and biophysical interactions. Biophy Rev. 2021;13:259-272.
• 6. Ali R, Siddiqui N. Biological Aspects of Emerging Benzothiazoles: A Short Review. Academic Editor: Gabriel Navarrete-Vazquez, Kaustubha Mohanty, Indian Institute of Technology Guwahati, India;2013. 7. Yadav PS, Senthilkumar GP. Benzothiazole: different methods of synthesis and diverse biological activities. Int J Pharm Sci Drug Res. 2011;3(1):1-7.
• 8. Achaiah G, Goud NS, Kumar KP, Mayuri P. Review on 2-substituted benzothiazoles: diversity of synthetic methods and biological activities. Int J Pharm Sci Drug Res. 2016;7(4):1375-1382.
• 9. Yadav R, Meena D, Singh K, Tyagi R, Yadav Y, Sagar R. Recent advances in the synthesis of new benzothiazole based anti-tubercular compounds. RSC Adv. 2023;13:21890-21925.
• 10. Achaiah G, Goud NS, Kumar KP, Mayuri P. Review on 2-substituted benzothiazoles: diversity of synthetic methods and biological activities. Int J Pharm Sci Res. 2016;7(4):1375-1382.
• 11. Yadav PS, Senthilkumar GP. Benzothiazole: different methods of synthesis and diverse biological activities. Int J Pharm Sci Drug Res. 2011;3(1):01–07.
• 12. Gill RK, Rawal RK, Bariwal J. Recent advances in the chemistry and biology of benzothiazoles. Arch Pharm Chem Life Sci. 2015;348(3):155–178.
• 13. Singh M, Verma H, Bhandu P, et al. Network analysis guided designing of multi-targeted anti-fungal agents: synthesis and biological evaluation. J Mol Struct. 2023;1272:134128.
• 14. Wang X, Zhao M, Chang Y, et al. Identification of novel benzothiazole derivatives as inhibitors of NEDDylation pathway to inhibit the progression of gastric cancer. Bioorg Med Chem Let. 2024;100:129647. 15. Galieva NA, Saveliev DA, Eltsov OS, et al. Antimicrobial activity of new benzazolyl N-sulfonyl amidines. Mendeleev Commun. 2021;31(4):495-497.
• 16. Sharma N, Srivastava N, Kaushal A, et al. Synthesis, in silico study and biological evaluation of N-(benzothiazol/thiazol-2-yl)benzamide derivatives as quorum sensing inhibitors against pseudomonas aeruginosa. Chem Biodiv. 2023;20(9):e202300647.
• 17. Shadap L, Agarwal N, Chetry V, Poluri KM, Kaminsky W, Kollipara MR. Arene ruthenium, rhodium and iridium complexes containing benzamide derivative ligands: Study of interesting bonding modes, antibacterial, antioxidant and DNA binding studies. J Organomet Chem. 2021:937:121731.
• 18. Al-Farraj ES, Fetoh A. Synthesis of new Fe(III), Co(II), and Cr(III) complexes of N-(benzo[d]thiazol-2-ylcarbamothioyl)benzamide (H2L2): Structural characterization and biological activities. App Organomet Chem. 2023;37(11):e7248.
• 19. Bonnett S, Jee J, Chettiar S, et al. Identification of 2-amino benzothiazoles with bactericidal activity against Mycobacterium tuberculosis. Microbio Spect. 2023;11(1):1-17.
• 20. Early J, Ollinger J, Darby C, et al. Identification of Compounds with pH-Dependent Bactericidal Activity against Mycobacterium tuberculosis. ACS Infec Dis. 2019;5(2):272-280.
• 21. Alazmaa HM, Avupati VR, Santiago C. Synthesis, characterization, in vitro biological evaluation of a series of benzothiazole amides as antibacterial agents. Asian J Chem. 2024;36(4):963-968.
• 22. Gurram SR, Azam MA. Design, synthesis and biological evaluation of some novel N'-(1,3-benzothiazol-2-yl)-arylamide derivatives as antibacterial agents. Chem Pap. 2021;75(10):5435-5452.
• 23. Taj MB, Tirmizi SA, Raheel A, et al. Facile synthesis of N-phenyl benzamidine derivatives, their skin protecting, and anti-aging activity. Russian J Gen Chem. 2018;88(11):2425-2431.
• 24. Sovic I, Cindric M, Perin N, et al. Biological potential of novel methoxy and hydroxy substituted heteroaromatic amides designed as promising antioxidative agents: synthesis, 3D-QSAR analysis, and biological activity. Chem Res Toxic. 2019;32(9):1880-1892.
• 25. Wei Y, Zhang M, Lyu Z, et al. Benzothiazole amides as TRPC3/6 Inhibitors for gastric cancer treatment. ACS Omega. 2021;6(13):9196-9203.
• 26. Ricci F, Angeli A, Mancuso F, De Luca L, Supuran CT, Gitto R. Screening campaign and docking ınvestigations in ıdentifying new hit compounds as ınhibitors of human carbonic anhydrases expressed in tumour cells. Chem Med Chem. 2023;18(20):e202300330.
• 27. Chiou JT, Wu YY, Lee YC, Chang LS. BCL2L1 inhibitor A-1331852 inhibits MCL1 transcription and triggers apoptosis in acute myeloid leukemia cells. Biochem Pharm. 2023;215:115738.
• 28. Dias RFC, Ribeiro BMRM, Cassani NM, et al. Discovery and structural optimization of a new series of N-acyl-2-aminobenzothiazole as inhibitors of Zika virus. Bioorg Med Chem. 2023;95(15):117488.
• 29. Substituted benzo-1,3-hetero-azoles useful in treatment of tuberculosis and their preparation. Assignee: Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, China, CN103772376 A 2014-05-07.
• 30. Dittmar M, Whig K, Miller J, et al. Nucleoside analogs NM107 and AT-527 are antiviral against rubella virus. PNAS Nexus, 2023;2(9):1-8.
• 31. Maus H, Barthels F, Hammerschmidt SJ, et al. SAR of novel benzothiazoles targeting an allosteric pocket of DENV and ZIKV NS2B/NS3 proteases. Bioorg Med Chem. 2021;47:116392.
• 32. Leal ES, Aucar MG, Gebhard LG, et al. Discovery of novel dengue virus entry inhibitors via a structure-based approach. Bioorg Med Chem. 2017;27(16):3851-3855.
• 33. Jyothi M, Ranganatha VL, Khamees HA, Khadri MJN, Khanum SA. Design, synthesis, characterization and analysis of anti-inflammatory properties of novel N-(benzo[d]thiazol-2-yl)-2-[phenyl(2-(piperidin-1-yl)ethylamino]benzamides and N-(benzo[d]thiazol-2-yl)-2-[phenyl(2-morpholino)ethylamino]benzamides derivatives through in vitro and in silico approach. J Iranian Chem Soc. 2023;20(4):861-873.
• 34. Aziz DM, Hassan SA, Amin AAM, Abdullah MN, Qurbani K, Aziz SB. A synergistic investigation of azo-thiazole derivatives incorporating thiazole moieties: a comprehensive exploration of their synthesis, characterization, computational insights, solvatochromism and multimodal biological activity assessment. RSC Adv. 2023;13(49):34534-34555.
• 35. Taj MB, Raheel A, Alelwani W, et al. One-Pot CuO-catalyzed green synthesis of N(N')-arylbenzamidines as potential enzyme inhibitors. Russian J Org Chem. 2019;55(7):1047-1052. 36. Lapierre TJWJD, Farago DN, de Moura Lodi Cruz MGF, et al. Evaluation and discovery of novel benzothiazole derivatives as promising hits against Leishmania İnfantum. Chem Bio Drug Des. 2024;103(4):e14525.
• 37. Amides as apolipoprotein A-I expression stimulators Assignee: Shionogi and Co. Ltd. Japan, JP2001139550 A 2001-05-22.
• 38. Ramos S, Vicente-Blazquez A, Lopez-Rubio M, Gallego-Yerga L, Alvarez R, Pelaez R. Frentizole, a nontoxic immuno suppressive drug, and its analogs display antitumor activity via tubulin inhibition. Inter J Mol Sci. 2023;24(24):17474.
• 39. Chini MG, Giordano A, Potenza M, et al. Targeting mPGES-1 by a combinatorial approach: identification of the aminobenzothiazole scaffold to suppress PGE levels. ACS Med Chem Let. 2020;11(5):783-789.
• 40. Ajou University, Industry-Academic Cooperation Foundation Composition for preventing or treating neurofibrosarcoma. Korea, Republic of, KR1902845 B1 2018-10-02.
• 41. Preparation of aromatic and heterocyclic carboxamides as antineoplastic agents. Assignee: Pfizer Inc European Patent Organization, EP343893 A1 1989-11-29.
• 42. Ismail MMF, Abdulwahab HG, Nossier ES, El Menofy NG, Abdelkhalek BA. Synthesis of novel 2-aminobenzothiazole derivatives as potential antimicrobial agents with dual DNA gyrase/topoisomerase IV inhibition. Bioorg Chem. 2020;94:103437.
• 43. Angulo-Cornejo J, Lino-Pacheco M, Richter R, Hennig L, Hallmeier KH, Beyer L. Metal chelates of N-benzothiazol-2-yl-, N-benzoxazol-2-yl- and N-(1H-benzimidazol-2-yl)-benzamide. Inorg Chim Acta. 2000;305(1):38-45.
• 44. Zheng H, Li YX, Xiong WC, et al. Mechanistic insights into diversified photoluminescence behaviors of BF2 complexes of N-benzoyl 2-aminobenzothiazoles. Phys Chem Chem Phy. 2024;26(15):11611-11617. 45. Caruso U, Panunzi B, Roviello A, Tingoli M, Tuzi A. Two aminobenzothiazole derivatives for Pd(II) and Zn(II) coordination. Inorg Chem Commun. 2011;14(1):46-48.
• 46. Irzoqi AA, Salman FA, Alasadi YK, Alheety MA. Synthesis and structural characterization of palladium(II) mixed-ligand complexes of N-(benzothiazol-2-yl)benzamide and 1,2-bis(diphenylphosphino)ethane. Inorg Chem. 2021;60(24):18854-18858.
• 47. Nakamoto K, Infrared and raman spectra of inorganic and coordination compounds. 5th ed NewYork: Wiley-Interscience, 1997:232.
• 48. Ameen M, Ahmed F. Preparation and characterization of some complexes of nickel(II), copper (II), and zinc (II) with decylxanthate and their adducts with nitrogen base ligands, and their biological activity. J Turkish Chem Soc Sec A: Chem. 2023;10(4):975-84.
• 49. Canpolat E, Aglamis A, Şahal H, Kaya M. Some transition metal complexes of NO type schiff base: preparation and characterization. Fac Sci Cumhuriyet Univ. 2016;37(1):65-73.
• 50. Geary WJ. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coord Chem Rev. 1971;7(1):81-122.