Mechanochemical Synthesis and Potentiation of the Antimicrobial Activity of 4-[3-(4-methoxyphenyl)-allylideneamino]-1,5-dimethyl-2-phenylpyrazol-3-one by Metal Chelation

  • Onyinye Chinelo Aguzue Sheda Science and Technology Complex, Abuja, Nigeria
  • Adebiyi Adedayo Sheda Science and Technology Complex, Abuja, Nigeria
  • Oviawe Amowie Phillip Department of Chemistry, University of Benin, Nigeria
Keywords: mechanochemical; methoxycinnamaldehyde, 4-[3-(4-methoxyphenyl)-allylideneamino]-1,5-dimethyl-2-phenylpyrazol-3-one, 4-aminioantipyrine

Abstract

A Schiff base ligand, 4-[3-(4-methoxyphenyl)-allylideneamino]-1,5-dimethyl-2-phenylpyrazol-3-one has been synthesized by the condensation of Methoxycinnamaldehyde and 4-aminoantipyrine. Its divalent metal complexes of Co, Ni, and Cu were also synthesized using the mechanochemical solvent-free method. The ligand and the complexes were characterized by FTIR, UV/visible, 1H NMR, 13C NMR, and GC-MS. The ligand behaved as a bidentate donor by using its carbonyl and azomethine N as binding sites for the metals. The ligand showed low activity against some microbes but the complexes were remarkably active against the fungi species.

References

Abdul, R. (2005). Synthesis and biological studies of some Schiff base compounds and their transition metal complexes. (Ph.D Thesis). Babauddin Zakariya University, Pakistan.

Agarwal, R.K., Singh, L., Sharma, D.K. (2006). Synthesis, spectral, and biological properties of copper(II) complexes of thiosemicarbazones of Schiff bases derived from 4-aminoantipyrine and aromatic aldehydes. Bioinorganic Chemistry and Applications, 1, 1-10.

Aguzue, O.C. (2019). Spectroscopic characterization and biological properties of schiff base ligands derived from cinnamaldehyde and their metal complexes of Co, Ni and Cu. Ph.D Thesis University of Benin.

Bahl, B.S., Bahl, A. (1993). Elementary Organic Chemistry, Schand and Company Ltd, New Delhi.

El-Hassy, N.A. (2004). Synthesis and investigation of tridentate Schiff base chelates. Master Thesis Benghazi Garyounis University.

Kuo, C.H., Jung, S.C., Lien, C.C., Chun, C.L. (2009). 4-methoxycinnamaldehyde inhibited human respiratory syncytial virus in a human larynx carcinoma cell line. Phytomedicine, 16, 882-886.

Obasi, L. N., Kaior, G. U., Rhyman, L., Alswaidan, I. A., Fun, H. K., (2016). Synthesis, characterization, antimicrobial screening and computational studies of 4-[3-(4-methoxy-phenyl)-allylideneamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one. Journal of Molecular Structure, 1120, 180-186.

Ooi, L.S., Li, Y., Kam, S.L., Wang, E.Y., Ooi, V.E. (2006). Antimicrobial activities of cinnamon oil and cinnamaldehyde from the Chinese medical herb Cinnamonium cassia Blume. The American Journal of Chinese Medicine, 34, 511-522.

Quiroga, A.G., Perez, J.M., Lopez-Solera, I. (1988). Novel tetranuclear orthometalated complexes of Pd(II) and Pt(II) derived from pisopropylbenzaldehyde thiosemicarbazone with cytotoxic activity in cis-DDP resistant tumor cell lines Interaction of these complexes with DNA. Journal of Medicinal Chemistry, 41(9), 1399-1408.

Scovill, J.P., Klayman D.L., Franchino, C.F. (2009). 2-acetylpyridine thiosemicarbazones complexes with transition metals as antimalarial and antileukemic agents. Journal of Medicinal Chemistry, 25(10), 1261-1264.

Shipman, J. (1986). Thiosemicarbazones of 2-acetylpyridine, 2-acetylquinoline, 1-acetylisoquinoline, and related compounds as inhibitors of herpes simplex virus in vitro and in a cutaneous herpes guinea pig model. Antiviral Research, 6(4), 197-222.

Sulekh, C., Amit, K.S. (2009). Antitingal and spectra studies of Cr(III) and Mn(II) compexes derived from 3, 31-thiodropropionic acid derivative. International Journal of Inorganic Chemistry, 89, 1-4.

Suresh, P., Jdhav, S.D., Shinde, S.K. (2012). CES as an efficient natural catalyst for synthesis of Schiff bases under solvent-free conditions: an innovative green approach. Organic Chemistry International, 10, 1-5.

Tanaka, K., Toda, F. (2000). Solvent free organic synthesis. Chemistry Reviews, 100, 1024-1074.
Published
2020-03-10
How to Cite
Aguzue, O. C., Adedayo, A., & Phillip, O. A. (2020). Mechanochemical Synthesis and Potentiation of the Antimicrobial Activity of 4-[3-(4-methoxyphenyl)-allylideneamino]-1,5-dimethyl-2-phenylpyrazol-3-one by Metal Chelation. Journal of Science and Mathematics Letters, 8(2), 15-21. https://doi.org/10.37134/jsml.vol8.2.3.2020