Metal Complexes of Heterocyclic Sulphonamide: Synthesis, Characterization and Biological Activity

Kingsley John Orie; Remy Ukachukwu Duru; Raphael I-oro Ngochindo

doi:doi:10.11648/j.sjac.20210904.14

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Metal Complexes of Heterocyclic Sulphonamide: Synthesis, Characterization and Biological Activity

Kingsley John Orie, Remy Ukachukwu Duru, Raphael I-oro Ngochindo

Published in Science Journal of Analytical Chemistry (Volume 9, Issue 4)

Received: 16 November 2021 Accepted: 2 December 2021 Published: 9 December 2021

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Abstract

The metal complex of heterocyclic sulphonamide with aminopyridine is a substantial class of pharmaceutical drugs used to treat infection, diabetes, anti-inflammatory issues and neurological disorders in the field of medicinal chemistry. The research reports the synthesis, characterization and biological activity of metal complexes of heterocyclic sulphonamide of aminopyridine. Sulphonamide of heterocyclic pyridine was synthesized by reacting 2-aminopyridine and tosyl chloride in an aqueous alkaline solution at ambient temperature. The iron (II) and copper (II) complexes of the ligand were also synthesized and recrystallized with suitable solvents, and the purity levels were ascertained with melting point and thin layer chromatographic pattern. Structural elucidation of the compounds was done via Nuclear Magnetic Resonance (NMR), Ultraviolet-Visible Spectroscopy (UV-VIS) Infrared (IR), Electrospray Ionization Mass Spectrometry (ESI-MS) Micro elemental analysis. Some absorption bands in the IR spectrum of heterocyclic sulphonamide derivatives were found to shift either to higher or lower wavenumbers in the complexes, indicating the involvement of azomethine nitrogen in coordination with the metal ion. The synthesized ligand and its metal complexes were screened for antimicrobial activity against Gram (-) Escherichia coli, Gram (-) Salmonella typhi, Gram (+) Staphylococcus aureus, Aspergillus flavus, Aspergillus niger and Saccharomyces cerevisiae. The ligand did not show activity against the selected bacterial and fungal strains whereas; some of the coordinated ligands gave a substantial improvement on their bactericidal and fungicidal activity. The complex of copper (II) was not bioactive to all the bacteria strains but sensitive to all the fungi strains. The complex of iron (II) was susceptible to the bacteria and fungi strains, except Aspergillus flavus that was inactive. When compared to Ciprofloxacin and Ketoconazole, with a broad-spectrum antibiotic, the standard antimicrobial agents were better in sensitivity than the synthesized compound.

Published in	Science Journal of Analytical Chemistry (Volume 9, Issue 4)
DOI	10.11648/j.sjac.20210904.14
Page(s)	104-109
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2021. Published by Science Publishing Group

Keywords

Biological Activity, Metal Complexes, Sulphonamide, Synthesis

References

[1]	Choudhury, R., Panda, S. & Singh, D. V. (2012). Emergence and dissemination of antibiotic resistance: a global problem. Indian journal of medical microbiology, 30 (4), 384.
[2]	Morehead, M. S. & Scarbrough, C. (2018). Emergence of global antibiotic resistance. Prim Care, 45 (3), 467-484.
[3]	Abdul Qadir, M. Ahmed, M. Aslam, H. Waseem S.& Shafiq, M. I. (2015). Amidine sulphonamides and benzene sulfonamides: Synthesis and their biological evaluation. Journal of Chemistry. 2015. doi.org/10.1155/2015/524056.
[4]	Orie, K. J., Duru, R. U. & Ngochindo, R. I (2021) Synthesis and Complexation of Monotosylated 4-Aminopyridine with Nickel (II) and Iron (II) Ions, Makara Journal of Science, 25 (3), 172−179. DOI: 10.7454/mss.v25i3.1242.
[5]	Duru, I. A., Ngochindo, R. I., Duru, C. E., Ogukwe, C. E., & Orji, I. (2014). Chlorinated Imidazole Complexes as Potent Antifungal Agents. Journal of Applied Chem, 7 (9), 20-23.
[6]	Deng, X., & Mani, N. S. (2006). A facile, environmentally benign sulfonamide synthesis in water. Green Chemistry, 8 (9), 835-838.
[7]	Jisha, M. J. & Isac Sobana raj, C. (2017) Synthesis and characterization of Schiff base complexes of Cu, Ni (II), Co (II) complexes of Schiff base derived from furan 3- carboxaldehyde and 3-aminopyridine. International Journal of Science and Research Publication 7 (10).
[8]	Don-Lawson, C., Okah, R. & Orie, K. J. (2020). Synthesis and corrosion inhibition study of mild steel in 0.5 M hydrochloric acid by 1-((2- arbamoylguanidino) (furan-2-ylmethyl) urea. Direct Research Journal of Chemistry and Material Science, 7 (1), 1-6. DOI: https://doi.org/ 10.26765/DRJCMS623398016
[9]	Dojer, B. Pevec, A. Belaj, F. & Kristl, M. (2015). Two New Zinc (II) Acetate with 3- and 4- Aminopyridine; Syntheses and Structural Properties. Acta Chimica Slovenica 62 (2): 312-8. Doi. 10. 17344/acsi/2014.1111.
[10]	Salehi, M., Kubicki, M., Galini, M., Jafari, M., & Malekshah, R. E. (2019). Synthesis, characterization and crystal structures of two novel sulfa drug Schiff base ligands derived sulphonamide and molecular docking study. Journal of Molecular Structure, 1180, 595-602. https://doi.org/10.1016/j.molstruc.2018.12.002
[11]	Orie, K. J., Duru, R. U. & Ngochindo, R. I. (2021). Syntheses, complexation and biological activity of aminopyridine: A mini-review. Am. J. Heterocycl. Chem. 7 (2): 11–25, https://doi.org/10.11648/ j.ajhc.20210702.11.
[12]	Rehman, H., Abdul Qadir, M., Shad, H. A. & Khan, Z. I. (2017). One-pot synthesis of some novel sulphonamide derivatives containing-NH₂ group: spectral characterization and biological evaluation. Medicinal Chemistry 7: 252-6. htt. doi: 10.4172/2161- 0444.1000465.
[13]	Istrefi, Q., Türkeş, C., Arslan, M., Demir, Y., Nixha, A. R., Beydemir, Ş., & Küfrevioğlu, Ö. İ. (2020). Sulphonamides incorporating ketene N, S-acetal bioisosteres as potent carbonic anhydrase and acetylcholinesterase inhibitors. Archiv Der Pharmazie, 353 (6), 1900383., https://doi.org/10.1002/ardp.201900383
[14]	Işık, M., Demir, Y., Durgun, M., Türkeş, C., Necip, A., & Beydemir, Ş. (2020). Molecular docking and investigation of 4-(benzylideneamino)-and 4-(benzylamino)-benzenesulphonamide derivatives as potent AChE inhibitors. Chemical Papers, 74 (5), 1395-1405. https://doi.org/10.1007/s11696-019-00988-3
[15]	Pervaiz, M., Riaz, A., Munir, A., Saeed, Z., Hussain, S., Rashid, A. & Adnan, A. (2020). Synthesis and characterization of sulphonamide metal complexes as antimicrobial agents. Journal of Molecular Structure, 1202, 127284. https://doi.org/10.1016/j.molstruc.2019.127284
[16]	Diaconu, D., Mangalagiu, V., Amariucai-Mantu, D., Antoci, V., Giuroiu, C. L., & Mangalagiu, I. I. (2020). Hybrid quinoline-sulfonamide complexes (M2+) derivatives with antimicrobial activity. Molecules, 25 (12), 2946. https://doi.org/10.3390/molecules25122946
[17]	Naaz, F., Srivastava, R., Singh, A., Singh, N., Verma, R., Singh, V. K. & Singh, R. K. (2018). Molecular modeling, synthesis, antibacterial and cytotoxicity evaluation of sulphonamide derivatives of benzimidazole, indazole, benzothiazole and thiazole. Bioorganic & medicinal chemistry, 26 (12), 3414-3428. https://doi.org/10.1016/j.bmc.2018.05.015
[18]	Sayed, A. M., Taher, F. A., Abdel-Samad, M. R., El-Gaby, M. S., El-Adl, K., & Saleh, N. M. (2021). Design, synthesis, molecular docking, in silico ADMET profile and anticancer evaluations of sulphonamide endowed with hydrazone-coupled derivatives as VEGFR-2 inhibitors. Bioorganic Chemistry, 108, 104669. https://doi.org/10.1016/j.bioorg.2021.104669
[19]	Isyaku, Y., Uzairu, A., & Uba, S. (2020). Computational studies of a series of 2-substituted phenyl-2-oxo-, 2-hydroxyl-and 2-acylloxyethylsulphonamides as potent anti-fungal agents. Heliyon, 6 (4), e03724 https://doi.org/10.1016/j.heliyon.2020.e03724.
[20]	Al-Noor, T. H. (2012). Synthesis and Characterization of metal complexes with ligands containing a hetero (N) atom and (hydroxyl or carboxyl) group. International Journal for Sciences and Technology, 7 (2).
[21]	Andrews, J. M. (2001). Determination of minimum inhibitory concentrations. Journal of antimicrobial Chemotherapy, 48 (1), 5-16. https://doi.org/10.1093/jac/48.suppl_1.5
[22]	Vedel, G. (2005). Simple method to determine β-lactam resistance phenotypes in Pseudomonas aeruginosa using the disc agar diffusion test. Journal of antimicrobial chemotherapy, 56 (4), 657-664. https://doi.org/10.1093/jac/dki303
[23]	Sobola A. O. & Watkins, G. M. (2018). Synthesis, characterization and biological study of Cu (II) complexes of aminopyridine and (aminomethyl) pyridine Schiff bases. Journal of the Serbian Chemical Society 83 (7-8): 809-19. doi.org/10.2298/JSC170913002S.
[24]	Igwe, C. N. & Okoro, U. C. (2014). Synthesis, characterization, and evaluation for antibacterial and antifungal activities of n-heteroaryl substituted benzene sulphonamides. Organic Chemistry International 2014. doi.org/10.1155/2014/419518.
[25]	Ijeomah, A., & Tseeka, M. (2021). synthesis, characterisation and antibacterial activity of 2-(phenyl sulfonyl) aminopyridine. Journal of Chemical Society of Nigeria, 46 (1), 110-113. DOI: https://doi.org/10.46602/jcsn.v46i1.573.
[26]	Lakrout, S. K'tir, H. Amira, A. Berredjem, M. & Aouf, N. E. (2014). A simple and eco-sustainable method for the sulphonylation of amines under microwave-assisted solvent-free conditions. RSC Advances 4 (31): 16027-16032. doi.org/10.1039/C4RA01346H.

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APA Style

Kingsley John Orie, Remy Ukachukwu Duru, Raphael I-oro Ngochindo. (2021). Metal Complexes of Heterocyclic Sulphonamide: Synthesis, Characterization and Biological Activity. Science Journal of Analytical Chemistry, 9(4), 104-109. https://doi.org/10.11648/j.sjac.20210904.14

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ACS Style

Kingsley John Orie; Remy Ukachukwu Duru; Raphael I-oro Ngochindo. Metal Complexes of Heterocyclic Sulphonamide: Synthesis, Characterization and Biological Activity. Sci. J. Anal. Chem. 2021, 9(4), 104-109. doi: 10.11648/j.sjac.20210904.14

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AMA Style

Kingsley John Orie, Remy Ukachukwu Duru, Raphael I-oro Ngochindo. Metal Complexes of Heterocyclic Sulphonamide: Synthesis, Characterization and Biological Activity. Sci J Anal Chem. 2021;9(4):104-109. doi: 10.11648/j.sjac.20210904.14

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@article{10.11648/j.sjac.20210904.14,
  author = {Kingsley John Orie and Remy Ukachukwu Duru and Raphael I-oro Ngochindo},
  title = {Metal Complexes of Heterocyclic Sulphonamide: Synthesis, Characterization and Biological Activity},
  journal = {Science Journal of Analytical Chemistry},
  volume = {9},
  number = {4},
  pages = {104-109},
  doi = {10.11648/j.sjac.20210904.14},
  url = {https://doi.org/10.11648/j.sjac.20210904.14},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjac.20210904.14},
  abstract = {The metal complex of heterocyclic sulphonamide with aminopyridine is a substantial class of pharmaceutical drugs used to treat infection, diabetes, anti-inflammatory issues and neurological disorders in the field of medicinal chemistry. The research reports the synthesis, characterization and biological activity of metal complexes of heterocyclic sulphonamide of aminopyridine. Sulphonamide of heterocyclic pyridine was synthesized by reacting 2-aminopyridine and tosyl chloride in an aqueous alkaline solution at ambient temperature. The iron (II) and copper (II) complexes of the ligand were also synthesized and recrystallized with suitable solvents, and the purity levels were ascertained with melting point and thin layer chromatographic pattern. Structural elucidation of the compounds was done via Nuclear Magnetic Resonance (NMR), Ultraviolet-Visible Spectroscopy (UV-VIS) Infrared (IR), Electrospray Ionization Mass Spectrometry (ESI-MS) Micro elemental analysis. Some absorption bands in the IR spectrum of heterocyclic sulphonamide derivatives were found to shift either to higher or lower wavenumbers in the complexes, indicating the involvement of azomethine nitrogen in coordination with the metal ion. The synthesized ligand and its metal complexes were screened for antimicrobial activity against Gram (-) Escherichia coli, Gram (-) Salmonella typhi, Gram (+) Staphylococcus aureus, Aspergillus flavus, Aspergillus niger and Saccharomyces cerevisiae. The ligand did not show activity against the selected bacterial and fungal strains whereas; some of the coordinated ligands gave a substantial improvement on their bactericidal and fungicidal activity. The complex of copper (II) was not bioactive to all the bacteria strains but sensitive to all the fungi strains. The complex of iron (II) was susceptible to the bacteria and fungi strains, except Aspergillus flavus that was inactive. When compared to Ciprofloxacin and Ketoconazole, with a broad-spectrum antibiotic, the standard antimicrobial agents were better in sensitivity than the synthesized compound.},
 year = {2021}
}

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TY  - JOUR
T1  - Metal Complexes of Heterocyclic Sulphonamide: Synthesis, Characterization and Biological Activity
AU  - Kingsley John Orie
AU  - Remy Ukachukwu Duru
AU  - Raphael I-oro Ngochindo
Y1  - 2021/12/09
PY  - 2021
N1  - https://doi.org/10.11648/j.sjac.20210904.14
DO  - 10.11648/j.sjac.20210904.14
T2  - Science Journal of Analytical Chemistry
JF  - Science Journal of Analytical Chemistry
JO  - Science Journal of Analytical Chemistry
SP  - 104
EP  - 109
PB  - Science Publishing Group
SN  - 2376-8053
UR  - https://doi.org/10.11648/j.sjac.20210904.14
AB  - The metal complex of heterocyclic sulphonamide with aminopyridine is a substantial class of pharmaceutical drugs used to treat infection, diabetes, anti-inflammatory issues and neurological disorders in the field of medicinal chemistry. The research reports the synthesis, characterization and biological activity of metal complexes of heterocyclic sulphonamide of aminopyridine. Sulphonamide of heterocyclic pyridine was synthesized by reacting 2-aminopyridine and tosyl chloride in an aqueous alkaline solution at ambient temperature. The iron (II) and copper (II) complexes of the ligand were also synthesized and recrystallized with suitable solvents, and the purity levels were ascertained with melting point and thin layer chromatographic pattern. Structural elucidation of the compounds was done via Nuclear Magnetic Resonance (NMR), Ultraviolet-Visible Spectroscopy (UV-VIS) Infrared (IR), Electrospray Ionization Mass Spectrometry (ESI-MS) Micro elemental analysis. Some absorption bands in the IR spectrum of heterocyclic sulphonamide derivatives were found to shift either to higher or lower wavenumbers in the complexes, indicating the involvement of azomethine nitrogen in coordination with the metal ion. The synthesized ligand and its metal complexes were screened for antimicrobial activity against Gram (-) Escherichia coli, Gram (-) Salmonella typhi, Gram (+) Staphylococcus aureus, Aspergillus flavus, Aspergillus niger and Saccharomyces cerevisiae. The ligand did not show activity against the selected bacterial and fungal strains whereas; some of the coordinated ligands gave a substantial improvement on their bactericidal and fungicidal activity. The complex of copper (II) was not bioactive to all the bacteria strains but sensitive to all the fungi strains. The complex of iron (II) was susceptible to the bacteria and fungi strains, except Aspergillus flavus that was inactive. When compared to Ciprofloxacin and Ketoconazole, with a broad-spectrum antibiotic, the standard antimicrobial agents were better in sensitivity than the synthesized compound.
VL  - 9
IS  - 4
ER  -

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Author Information

Kingsley John Orie

Department of Pure and Industrial Chemistry, University of Port Harcourt, Port Harcourt, Nigeria
Remy Ukachukwu Duru

Department of Pure and Industrial Chemistry, University of Port Harcourt, Port Harcourt, Nigeria
Raphael I-oro Ngochindo

Department of Pure and Industrial Chemistry, University of Port Harcourt, Port Harcourt, Nigeria

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Kingsley John Orie, Remy Ukachukwu Duru, Raphael I-oro Ngochindo. (2021). Metal Complexes of Heterocyclic Sulphonamide: Synthesis, Characterization and Biological Activity. Science Journal of Analytical Chemistry, 9(4), 104-109. https://doi.org/10.11648/j.sjac.20210904.14

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ACS Style

Kingsley John Orie; Remy Ukachukwu Duru; Raphael I-oro Ngochindo. Metal Complexes of Heterocyclic Sulphonamide: Synthesis, Characterization and Biological Activity. Sci. J. Anal. Chem. 2021, 9(4), 104-109. doi: 10.11648/j.sjac.20210904.14

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AMA Style

Kingsley John Orie, Remy Ukachukwu Duru, Raphael I-oro Ngochindo. Metal Complexes of Heterocyclic Sulphonamide: Synthesis, Characterization and Biological Activity. Sci J Anal Chem. 2021;9(4):104-109. doi: 10.11648/j.sjac.20210904.14

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@article{10.11648/j.sjac.20210904.14,
  author = {Kingsley John Orie and Remy Ukachukwu Duru and Raphael I-oro Ngochindo},
  title = {Metal Complexes of Heterocyclic Sulphonamide: Synthesis, Characterization and Biological Activity},
  journal = {Science Journal of Analytical Chemistry},
  volume = {9},
  number = {4},
  pages = {104-109},
  doi = {10.11648/j.sjac.20210904.14},
  url = {https://doi.org/10.11648/j.sjac.20210904.14},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjac.20210904.14},
  abstract = {The metal complex of heterocyclic sulphonamide with aminopyridine is a substantial class of pharmaceutical drugs used to treat infection, diabetes, anti-inflammatory issues and neurological disorders in the field of medicinal chemistry. The research reports the synthesis, characterization and biological activity of metal complexes of heterocyclic sulphonamide of aminopyridine. Sulphonamide of heterocyclic pyridine was synthesized by reacting 2-aminopyridine and tosyl chloride in an aqueous alkaline solution at ambient temperature. The iron (II) and copper (II) complexes of the ligand were also synthesized and recrystallized with suitable solvents, and the purity levels were ascertained with melting point and thin layer chromatographic pattern. Structural elucidation of the compounds was done via Nuclear Magnetic Resonance (NMR), Ultraviolet-Visible Spectroscopy (UV-VIS) Infrared (IR), Electrospray Ionization Mass Spectrometry (ESI-MS) Micro elemental analysis. Some absorption bands in the IR spectrum of heterocyclic sulphonamide derivatives were found to shift either to higher or lower wavenumbers in the complexes, indicating the involvement of azomethine nitrogen in coordination with the metal ion. The synthesized ligand and its metal complexes were screened for antimicrobial activity against Gram (-) Escherichia coli, Gram (-) Salmonella typhi, Gram (+) Staphylococcus aureus, Aspergillus flavus, Aspergillus niger and Saccharomyces cerevisiae. The ligand did not show activity against the selected bacterial and fungal strains whereas; some of the coordinated ligands gave a substantial improvement on their bactericidal and fungicidal activity. The complex of copper (II) was not bioactive to all the bacteria strains but sensitive to all the fungi strains. The complex of iron (II) was susceptible to the bacteria and fungi strains, except Aspergillus flavus that was inactive. When compared to Ciprofloxacin and Ketoconazole, with a broad-spectrum antibiotic, the standard antimicrobial agents were better in sensitivity than the synthesized compound.},
 year = {2021}
}

Copy | Download

TY  - JOUR
T1  - Metal Complexes of Heterocyclic Sulphonamide: Synthesis, Characterization and Biological Activity
AU  - Kingsley John Orie
AU  - Remy Ukachukwu Duru
AU  - Raphael I-oro Ngochindo
Y1  - 2021/12/09
PY  - 2021
N1  - https://doi.org/10.11648/j.sjac.20210904.14
DO  - 10.11648/j.sjac.20210904.14
T2  - Science Journal of Analytical Chemistry
JF  - Science Journal of Analytical Chemistry
JO  - Science Journal of Analytical Chemistry
SP  - 104
EP  - 109
PB  - Science Publishing Group
SN  - 2376-8053
UR  - https://doi.org/10.11648/j.sjac.20210904.14
AB  - The metal complex of heterocyclic sulphonamide with aminopyridine is a substantial class of pharmaceutical drugs used to treat infection, diabetes, anti-inflammatory issues and neurological disorders in the field of medicinal chemistry. The research reports the synthesis, characterization and biological activity of metal complexes of heterocyclic sulphonamide of aminopyridine. Sulphonamide of heterocyclic pyridine was synthesized by reacting 2-aminopyridine and tosyl chloride in an aqueous alkaline solution at ambient temperature. The iron (II) and copper (II) complexes of the ligand were also synthesized and recrystallized with suitable solvents, and the purity levels were ascertained with melting point and thin layer chromatographic pattern. Structural elucidation of the compounds was done via Nuclear Magnetic Resonance (NMR), Ultraviolet-Visible Spectroscopy (UV-VIS) Infrared (IR), Electrospray Ionization Mass Spectrometry (ESI-MS) Micro elemental analysis. Some absorption bands in the IR spectrum of heterocyclic sulphonamide derivatives were found to shift either to higher or lower wavenumbers in the complexes, indicating the involvement of azomethine nitrogen in coordination with the metal ion. The synthesized ligand and its metal complexes were screened for antimicrobial activity against Gram (-) Escherichia coli, Gram (-) Salmonella typhi, Gram (+) Staphylococcus aureus, Aspergillus flavus, Aspergillus niger and Saccharomyces cerevisiae. The ligand did not show activity against the selected bacterial and fungal strains whereas; some of the coordinated ligands gave a substantial improvement on their bactericidal and fungicidal activity. The complex of copper (II) was not bioactive to all the bacteria strains but sensitive to all the fungi strains. The complex of iron (II) was susceptible to the bacteria and fungi strains, except Aspergillus flavus that was inactive. When compared to Ciprofloxacin and Ketoconazole, with a broad-spectrum antibiotic, the standard antimicrobial agents were better in sensitivity than the synthesized compound.
VL  - 9
IS  - 4
ER  -

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