Synthesis, spectroscopic characterization and antibacterial activity of new series of Schiff base derived from 4-aminoantipyrine and 2-amino benzimidazole
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.
Azab ME, Rizk SA, Amr AE-GE. Synthesis of some novel heterocyclic and schiff base derivatives as antimicrobial agents. Molecules 2015; 20(10):18201–18.
Brzezinska-Rodak M, Peczynska-Czoch W. Biodegradation of N-heterocyclic compound. Biotechnologia 2000; 1:102–16.
Kumar J, Rai A, Raj V. A comprehensive review on the pharmacological activity of schiff base containing derivatives. Org Med Chem J 2017; 1:555–64.
Brodowska K, Lodyga-Chruscinska E. Schiff bases—interesting range of applications in various fields of science. Chem Inform 2015; 46(11).
Ashraf MA, Mahmood K, Wajid A, Maah MJ, Yusoff I. Synthesis, characterization and biological activity of Schiff bases. IPCBEE 2011; 10:1–7.
Qin W, Long S, Panunzio M, Biondi S. Schiff bases: A short survey on an evergreen chemistry tool. Molecules 2013; 18(10):12264–89.
MOHAMED GG, Omar MM, Hindy AM. Metal complexes of Schiff bases: preparation, characterization, and biological activity. Turkish Journal of Chemistry 2006; 30(3):361–82.
Deshmukh P, Kumar P, Kankoriya A, Halve AK, Dixit R. 4-Aminoantipyrine: a significant tool for the synthesis of biologically active Schiff bases and metal complexes. Int J Pharm Sci Rev Res 2015; 34(1):162–70.
Prakash A, Adhikari D. Application of Schiff bases and their metal complexes-A Review. Int J Chem Tech Res 2011; 3(4):1891–6.
Ibrahim MN, Sharif SE. Synthesis, characterization and use of Schiff bases as fluorimetric analytical reagents. Journal of Chemistry 2007; 4(4):531–5.
Ali P, Meshram J, Sheikh J, Tiwari V, Dongre R, Hadda TB. Predictions and correlations of structure activity relationship of some aminoantipyrine derivatives on the basis of theoretical and experimental ground. Medicinal Chemistry Research 2012; 21(2):157–64.
Alam MS, Lee D-U, Bari ML. Antibacterial and cytotoxic activities of Schiff base analogues of 4-aminoantipyrine. Journal of the Korean Society for Applied Biological Chemistry 2014; 57(5):613–9.
Li JJ. Williamson ether synthesis. Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications Fifth Edition. Cham: Springer International Publishing; 2014. p. 628.
Ahmad M, Siddiqui HL, Ahmad S, Irfan Ashiq M, Tizzard GJ. Methyl 4-acetoxy-2-methyl-2H-1, 2-benzothiazine-3-carboxylate 1, 1-dioxide. Acta Crystallographica Section E: Structure Reports Online 2008; 64(3):o594.
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