Synthesis, Characterization and Antibacterial Activity Evaluation of 4-amino Antipyrine Derivatives and Their Transition Metal Complexes

Salah Hamza Sherif; Dagne Addisu Kure; Endalkachew Asefa Moges; Bekele Argaw

doi:doi:10.11648/j.bio.20210901.12

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Synthesis, Characterization and Antibacterial Activity Evaluation of 4-amino Antipyrine Derivatives and Their Transition Metal Complexes

Salah Hamza Sherif, Dagne Addisu Kure, Endalkachew Asefa Moges, Bekele Argaw

Published in American Journal of Bioscience and Bioengineering (Volume 9, Issue 1)

Received: 26 December 2020 Accepted: 11 January 2021 Published: 23 February 2021

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Abstract

Due to their importance as catalysts in many reactions and their biological activities, an interest in the synthesis and characterization of transition metal complexes containing Schiff bases is increasing. Schiff base ligands have achieved considerable attention by the scientist over the decades as potential drug agent, Azomethine linkage (-CH=N-) of Schiff base play a significant role in medical chemistry. Derivatives of Schiff bases of 4-aminoantipyrine viz, 4-(2-hydroxy-3-methoxy benzylid ene amino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (4) and 4-((5-methylfuran-2-yl) methylene amino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (5) and their Co (II), Ni (II), Cu (II) complexes were successfully synthesized, the Schiff bases ligand (4) and (5) were synthesized by condensation reaction. The structures of all the synthesized ligands were confirmed by using IR, UV-Visible, ¹H NMR, and ¹³C NMR. The Cu (II), Ni (II) and Co (II) complexes were confirmed by using IR and VU-Visible. The complexes are electrolytic in nature as indicated by molar conductance measurements. The data have shown that all complexes possess octahedral geometry. In-vitro antibacterial activity of all the synthesized ligands and their metal complexes were carried out by using disc diffusion method against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa bacterial strain. Compound Co (4) has exhibited better antibacterial activity than the standard drug against S. aureus (25 mm zone of inhibition compared to the standard antibiotic Oxacillin (23 mm zone of inhibition).

Published in	American Journal of Bioscience and Bioengineering (Volume 9, Issue 1)
DOI	10.11648/j.bio.20210901.12
Page(s)	8-12
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

Schiff Base, 4-aminoantipyrine, Ortho-vanillin, 5-methyl Furfural, Transition Metal Complexes, Antimicrobial

References

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[3]	M. S. Alam, D.-U. Lee, M. L. Bari, (2014) Antibacterial and Cytotoxic Activities of Schiff Base Analogues of 4-Aminoantipyrine, J Korean Soc Appl Biol Chem., 57, 613−619
[4]	Sarbast Muhammed Ahmed, Kezhal M. Salih, Hiwa Omer Ahmad, Zanko H. Jawhar, Dashti H. Hamad (2019) Synthesis, spectroscopic characterization and antibacterial activity of new series of Schiff base derived from 4-aminoantipyrine and 2-amino benzimidazole. Zanco J. Med. Sci., 23, 206-216.
[5]	Kees KL, Fitzgerald JJ, Steiner KE, Mattes JF, Mihan B, Tosi T, Mondoro D, and McCalebr ML (1996) New potent antihyperglycemic agents in db/db mice: synthesis and structure-activity relationship studies of (4-substituted benzyl) (trifluoromethyl)pyrazoles and pyrazolones., J Med Chem. 39, 3920–8.
[6]	M. S. Alam, M. S. Alam (2012) Synthesis, Molecular Structure and Antioxidant Activity of (E)-4-[Benzylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one, a Schiff Base Ligand of 4-Aminoantipyrine. J Chem Crystallogr. 42, 93–102
[7]	Burdulene, D., Palaima, A., Stumbryavichyute Z., Talaikite Z. (1996) Synthesis and anti-inflammatory activity of 4-aminoantipyrine derivatives of succinamides. Pharm. Chem. J. 33,191-193.
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[11]	I. Mohanram and J. Meshram (2014) Synthesis and Biological Activities of 4-Aminoanti pyrine Derivatives Derived from Betti-Type Reaction, Hindawi Publishing Corporation ISRN Organic Chemistry 1-7.
[12]	M. M. Ghorab, M. G. El-Gazzar and M. S. Alsaid (2014) Synthesis, Characterization and Anti-Breast Cancer Activity of New 4-Aminoantipyrine-Based Heterocycles, Int. J. Mol. Sci. 15, 7539-7553.
[13]	G. H. Elgemeie, M. A. Abu-Zaied, S. A. Loutfy (2017) 4-Aminoantipyrine in carbohydrate research: Design, synthesis and anticancer activity of thioglycosides of a novel class of 4- aminoanti pyrines and their corresponding pyrazolopyrimidine and pyrazolopyridine thioglycosides, Tetrahedron 73, 5853-5861.
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APA Style

Salah Hamza Sherif, Dagne Addisu Kure, Endalkachew Asefa Moges, Bekele Argaw. (2021). Synthesis, Characterization and Antibacterial Activity Evaluation of 4-amino Antipyrine Derivatives and Their Transition Metal Complexes. American Journal of Bioscience and Bioengineering, 9(1), 8-12. https://doi.org/10.11648/j.bio.20210901.12

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ACS Style

Salah Hamza Sherif; Dagne Addisu Kure; Endalkachew Asefa Moges; Bekele Argaw. Synthesis, Characterization and Antibacterial Activity Evaluation of 4-amino Antipyrine Derivatives and Their Transition Metal Complexes. Am. J. BioSci. Bioeng. 2021, 9(1), 8-12. doi: 10.11648/j.bio.20210901.12

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AMA Style

Salah Hamza Sherif, Dagne Addisu Kure, Endalkachew Asefa Moges, Bekele Argaw. Synthesis, Characterization and Antibacterial Activity Evaluation of 4-amino Antipyrine Derivatives and Their Transition Metal Complexes. Am J BioSci Bioeng. 2021;9(1):8-12. doi: 10.11648/j.bio.20210901.12

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@article{10.11648/j.bio.20210901.12,
  author = {Salah Hamza Sherif and Dagne Addisu Kure and Endalkachew Asefa Moges and Bekele Argaw},
  title = {Synthesis, Characterization and Antibacterial Activity Evaluation of 4-amino Antipyrine Derivatives and Their Transition Metal Complexes},
  journal = {American Journal of Bioscience and Bioengineering},
  volume = {9},
  number = {1},
  pages = {8-12},
  doi = {10.11648/j.bio.20210901.12},
  url = {https://doi.org/10.11648/j.bio.20210901.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.bio.20210901.12},
  abstract = {Due to their importance as catalysts in many reactions and their biological activities, an interest in the synthesis and characterization of transition metal complexes containing Schiff bases is increasing. Schiff base ligands have achieved considerable attention by the scientist over the decades as potential drug agent, Azomethine linkage (-CH=N-) of Schiff base play a significant role in medical chemistry. Derivatives of Schiff bases of 4-aminoantipyrine viz, 4-(2-hydroxy-3-methoxy benzylid ene amino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (4) and 4-((5-methylfuran-2-yl) methylene amino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (5) and their Co (II), Ni (II), Cu (II) complexes were successfully synthesized, the Schiff bases ligand (4) and (5) were synthesized by condensation reaction. The structures of all the synthesized ligands were confirmed by using IR, UV-Visible, 1H NMR, and 13C NMR. The Cu (II), Ni (II) and Co (II) complexes were confirmed by using IR and VU-Visible. The complexes are electrolytic in nature as indicated by molar conductance measurements. The data have shown that all complexes possess octahedral geometry. In-vitro antibacterial activity of all the synthesized ligands and their metal complexes were carried out by using disc diffusion method against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa bacterial strain. Compound Co (4) has exhibited better antibacterial activity than the standard drug against S. aureus (25 mm zone of inhibition compared to the standard antibiotic Oxacillin (23 mm zone of inhibition).},
 year = {2021}
}

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TY  - JOUR
T1  - Synthesis, Characterization and Antibacterial Activity Evaluation of 4-amino Antipyrine Derivatives and Their Transition Metal Complexes
AU  - Salah Hamza Sherif
AU  - Dagne Addisu Kure
AU  - Endalkachew Asefa Moges
AU  - Bekele Argaw
Y1  - 2021/02/23
PY  - 2021
N1  - https://doi.org/10.11648/j.bio.20210901.12
DO  - 10.11648/j.bio.20210901.12
T2  - American Journal of Bioscience and Bioengineering
JF  - American Journal of Bioscience and Bioengineering
JO  - American Journal of Bioscience and Bioengineering
SP  - 8
EP  - 12
PB  - Science Publishing Group
SN  - 2328-5893
UR  - https://doi.org/10.11648/j.bio.20210901.12
AB  - Due to their importance as catalysts in many reactions and their biological activities, an interest in the synthesis and characterization of transition metal complexes containing Schiff bases is increasing. Schiff base ligands have achieved considerable attention by the scientist over the decades as potential drug agent, Azomethine linkage (-CH=N-) of Schiff base play a significant role in medical chemistry. Derivatives of Schiff bases of 4-aminoantipyrine viz, 4-(2-hydroxy-3-methoxy benzylid ene amino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (4) and 4-((5-methylfuran-2-yl) methylene amino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (5) and their Co (II), Ni (II), Cu (II) complexes were successfully synthesized, the Schiff bases ligand (4) and (5) were synthesized by condensation reaction. The structures of all the synthesized ligands were confirmed by using IR, UV-Visible, 1H NMR, and 13C NMR. The Cu (II), Ni (II) and Co (II) complexes were confirmed by using IR and VU-Visible. The complexes are electrolytic in nature as indicated by molar conductance measurements. The data have shown that all complexes possess octahedral geometry. In-vitro antibacterial activity of all the synthesized ligands and their metal complexes were carried out by using disc diffusion method against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa bacterial strain. Compound Co (4) has exhibited better antibacterial activity than the standard drug against S. aureus (25 mm zone of inhibition compared to the standard antibiotic Oxacillin (23 mm zone of inhibition).
VL  - 9
IS  - 1
ER  -

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Author Information

Salah Hamza Sherif

Department of Chemistry, Hawassa University, Hawassa, Ethiopia
Dagne Addisu Kure

Department of Chemistry, Hawassa University, Hawassa, Ethiopia
Endalkachew Asefa Moges

Department of Chemistry, Hawassa University, Hawassa, Ethiopia
Bekele Argaw

Department of Chemistry, Hawassa University, Hawassa, Ethiopia

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APA Style

Salah Hamza Sherif, Dagne Addisu Kure, Endalkachew Asefa Moges, Bekele Argaw. (2021). Synthesis, Characterization and Antibacterial Activity Evaluation of 4-amino Antipyrine Derivatives and Their Transition Metal Complexes. American Journal of Bioscience and Bioengineering, 9(1), 8-12. https://doi.org/10.11648/j.bio.20210901.12

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ACS Style

Salah Hamza Sherif; Dagne Addisu Kure; Endalkachew Asefa Moges; Bekele Argaw. Synthesis, Characterization and Antibacterial Activity Evaluation of 4-amino Antipyrine Derivatives and Their Transition Metal Complexes. Am. J. BioSci. Bioeng. 2021, 9(1), 8-12. doi: 10.11648/j.bio.20210901.12

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AMA Style

Salah Hamza Sherif, Dagne Addisu Kure, Endalkachew Asefa Moges, Bekele Argaw. Synthesis, Characterization and Antibacterial Activity Evaluation of 4-amino Antipyrine Derivatives and Their Transition Metal Complexes. Am J BioSci Bioeng. 2021;9(1):8-12. doi: 10.11648/j.bio.20210901.12

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@article{10.11648/j.bio.20210901.12,
  author = {Salah Hamza Sherif and Dagne Addisu Kure and Endalkachew Asefa Moges and Bekele Argaw},
  title = {Synthesis, Characterization and Antibacterial Activity Evaluation of 4-amino Antipyrine Derivatives and Their Transition Metal Complexes},
  journal = {American Journal of Bioscience and Bioengineering},
  volume = {9},
  number = {1},
  pages = {8-12},
  doi = {10.11648/j.bio.20210901.12},
  url = {https://doi.org/10.11648/j.bio.20210901.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.bio.20210901.12},
  abstract = {Due to their importance as catalysts in many reactions and their biological activities, an interest in the synthesis and characterization of transition metal complexes containing Schiff bases is increasing. Schiff base ligands have achieved considerable attention by the scientist over the decades as potential drug agent, Azomethine linkage (-CH=N-) of Schiff base play a significant role in medical chemistry. Derivatives of Schiff bases of 4-aminoantipyrine viz, 4-(2-hydroxy-3-methoxy benzylid ene amino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (4) and 4-((5-methylfuran-2-yl) methylene amino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (5) and their Co (II), Ni (II), Cu (II) complexes were successfully synthesized, the Schiff bases ligand (4) and (5) were synthesized by condensation reaction. The structures of all the synthesized ligands were confirmed by using IR, UV-Visible, 1H NMR, and 13C NMR. The Cu (II), Ni (II) and Co (II) complexes were confirmed by using IR and VU-Visible. The complexes are electrolytic in nature as indicated by molar conductance measurements. The data have shown that all complexes possess octahedral geometry. In-vitro antibacterial activity of all the synthesized ligands and their metal complexes were carried out by using disc diffusion method against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa bacterial strain. Compound Co (4) has exhibited better antibacterial activity than the standard drug against S. aureus (25 mm zone of inhibition compared to the standard antibiotic Oxacillin (23 mm zone of inhibition).},
 year = {2021}
}

Copy | Download

TY  - JOUR
T1  - Synthesis, Characterization and Antibacterial Activity Evaluation of 4-amino Antipyrine Derivatives and Their Transition Metal Complexes
AU  - Salah Hamza Sherif
AU  - Dagne Addisu Kure
AU  - Endalkachew Asefa Moges
AU  - Bekele Argaw
Y1  - 2021/02/23
PY  - 2021
N1  - https://doi.org/10.11648/j.bio.20210901.12
DO  - 10.11648/j.bio.20210901.12
T2  - American Journal of Bioscience and Bioengineering
JF  - American Journal of Bioscience and Bioengineering
JO  - American Journal of Bioscience and Bioengineering
SP  - 8
EP  - 12
PB  - Science Publishing Group
SN  - 2328-5893
UR  - https://doi.org/10.11648/j.bio.20210901.12
AB  - Due to their importance as catalysts in many reactions and their biological activities, an interest in the synthesis and characterization of transition metal complexes containing Schiff bases is increasing. Schiff base ligands have achieved considerable attention by the scientist over the decades as potential drug agent, Azomethine linkage (-CH=N-) of Schiff base play a significant role in medical chemistry. Derivatives of Schiff bases of 4-aminoantipyrine viz, 4-(2-hydroxy-3-methoxy benzylid ene amino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (4) and 4-((5-methylfuran-2-yl) methylene amino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (5) and their Co (II), Ni (II), Cu (II) complexes were successfully synthesized, the Schiff bases ligand (4) and (5) were synthesized by condensation reaction. The structures of all the synthesized ligands were confirmed by using IR, UV-Visible, 1H NMR, and 13C NMR. The Cu (II), Ni (II) and Co (II) complexes were confirmed by using IR and VU-Visible. The complexes are electrolytic in nature as indicated by molar conductance measurements. The data have shown that all complexes possess octahedral geometry. In-vitro antibacterial activity of all the synthesized ligands and their metal complexes were carried out by using disc diffusion method against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa bacterial strain. Compound Co (4) has exhibited better antibacterial activity than the standard drug against S. aureus (25 mm zone of inhibition compared to the standard antibiotic Oxacillin (23 mm zone of inhibition).
VL  - 9
IS  - 1
ER  -

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