Synthesis, spectroscopic characterization and antibacterial activity of new series of Schiff base derived from 4-aminoantipyrine and 2-amino benzimidazole

Sarbast Muhammed Ahmed; Kezhal M. Salih; Hiwa Omer Ahmad; Zanko H. Jawhar; Dashti H. Hamad

doi:10.15218/zjms.2019.026

Authors

Sarbast Muhammed Ahmed Department of Pharmaceutical Chemistry, College of Pharmacy, Hawler Medical University, Erbil, Iraq.
Kezhal M. Salih Department of Pharmaceutical Chemistry, College of Pharmacy, Hawler Medical University, Erbil, Iraq.
Hiwa Omer Ahmad Department of Pharmacy, Aynda Private Technical Institute, Erbil, Iraq.
Zanko H. Jawhar Department of Clinical Biochemistry, College of Health Sciences, Hawler Medical University, Erbil, Iraq.
Dashti H. Hamad Department of Clinical Biochemistry, College of Health Sciences, Hawler Medical University, Erbil, Iraq.

DOI:

https://doi.org/10.15218/zjms.2019.026

Keywords:

Schiff base, Williamson ether synthesis, Biological activity, Azomethine

Abstract

Background and objective: Compounds having imine or azomethine (–C=N–) functional group are known as Schiff bases. Schiff bases compounds are found to be an active pharmacophore for the design and development of various bioactive lead compounds. In this study, several new Schiff base compounds have been synthesized and characterized.

Methods: Williamson ether synthesis process has been used to synthesize -alkyloxy and substituted benzyloxy of benzaldehyde. Differently substituted ether benzaldehydes used to react with 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one in one hand and 1H-benzo[d]imidazol-2-amine on the other hand to produce Schiff base compounds.

Results: Synthesized ether derivative compounds (3a-e) were converted to new series of Schiff bases (4a-e and 5a-e) by condensation of equal molar amounts of compounds (3a-e) with different heterocyclic amines dissolved in absolute ethanol. All synthesized compounds were confirmed by (IR, ¹H-NMR, and ¹³CNMR) spectroscopy. All synthesized compounds were evaluated for antibacterial activities in vitro against Gram-positive and Gram-negative bacteria.

Conclusion: All compounds were purely synthesized, and all compounds were indicated growth inhibition against Escherichia coli, and Staphylococcus aureus, respectively with different inhibition zones staring from 13 to 33 mm.

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