Synthesis of Some novel Azomethine Oxide Derived from Aromatic Oximes and their Anti-microbial Studies

Mohammed, Jihad H. and Qaddo, Akram N. M. and Muhammad Salih, Nabaz A. and Omar, Faeza B. (2024) Synthesis of Some novel Azomethine Oxide Derived from Aromatic Oximes and their Anti-microbial Studies. ARO-THE SCIENTIFIC JOURNAL OF KOYA UNIVERSITY, 12 (1). pp. 13-18. ISSN 2410-9355

Text (Research Article) ARO.11471.VOL12.NO1.2024.ISSUE22-PP13-18.pdf - Published Version Available under License Creative Commons Attribution Non-commercial Share Alike. Download (546kB)

Abstract

The organic compound category known as azomethine oxides has garnered significant attention due to its potential for bioactive and pharmacological effects, as well as its role in organic syntheses. Existing literature offers various methods for producing derivatives of these compounds. This study, in particular, concentrates on the creation of several aromatic oximes through the reduction of corresponding aldehydes. Furthermore, these oximes are employed in the generation of new azomethine oxides through a condensation reaction with selected aldehydes. The molecular structure of the synthesized azomethine oxides is determined using techniques such as Fourier-transform infrared spectroscopy, 1H-NMR, and 13C-NMR. Finally, the antimicrobial effectiveness of these compounds was assessed against Escherichia coli (gram-negative bacteria), Staphylococcus aureus (gram-positive bacteria), and Candida albicans (fungus). The synthesized compounds were obtained with high purity and yielded excellent results. Furthermore, the data demonstrates that these azomethine oxides exhibit significant antimicrobial activity when compared to standard drugs.

Item Type:	Article
Additional Information:	Alshreimi, A.S., Zhang, G., Reidl, T.W., Peña, R.L., Koto, N.G., Islam, S.M., Wink, D.J., and Anderson, L.L., 2020. Synthesis of spirocyclic 1-pyrrolines from nitrones and arynes through a dearomative [3,3′]-sigmatropic rearrangement. Angewandte Chemie - International Edition, 59(35), pp.15244-15248. DOI: https://doi.org/10.1002/anie.202004652 Anderson, L.L., Kroc, M.A., Reidl, T.W., and Son, J., 2016. Cascade reactions of nitrones and allenes for the synthesis of indole derivatives. Journal of Organic Chemistry, 81(20), pp.9521-9529. DOI: https://doi.org/10.1021/acs.joc.6b01758 El Bouakher, A., Martel, A., and Comesse, S., 2019. α-halogenoacetamides: Versatile and efficient tools for the synthesis of complex aza-heterocycles. Organic and Biomolecular Chemistry, 17(37), pp.8467-8485. DOI: https://doi.org/10.1039/C9OB01683J Floyd, R.A., Hensley, K., Forster, M.J., Kelleher-Anderson, J.A., and Wood, P.L., 2002. Nitrones as neuroprotectants and antiaging drugs. Annals of the New York Academy of Sciences, 959, pp.321-329. DOI: https://doi.org/10.1111/j.1749-6632.2002.tb02103.x Floyd, R.A., Kopke, R.D., Choi, C.H., Foster, S.B., Doblas, S., and Towner, R.A.,2008. Nitrones as therapeutics. Free Radical Biology and Medicine, 45(10), pp.1361-1374. DOI: https://doi.org/10.1016/j.freeradbiomed.2008.08.017 Hiraoka, S., Matsumoto, T., Matsuzaka, K., Sato, T., and Chida, N., 2019. Approach to fully substituted cyclic nitrones from N-hydroxylactam derivatives: Development and application to the total synthesis of cylindricine C. Angewandte Chemie - International Edition, 58(13), pp.4381-4385. DOI: https://doi.org/10.1002/anie.201901049 Inouye, Y., Hara, J., and Kakisawa, H., 1980. Novel E-Z equilibrium of N-alkyl-alpha-alkoxycarbonylnitrone in solution. Chemistry Letters, 9, pp.1407-1410. DOI: https://doi.org/10.1246/cl.1980.1407 Kliegel, W., Metge, J., and Rettig, S.J., 1997. Synthesis of C-aryl-N-(2-hydroxyphenylmethyl)-nitrones and their reaction with diphenylborinic or carboxylic acid derivatives. Crystal and molecular structures of a free nitrone ligand and its diphenyl-boron chelate. Canadian Journal of Chemistry, 75, pp.1830-1843. DOI: https://doi.org/10.1139/v97-616 Li, T.Z., Liu, S.J., Sun, Y.W., Deng, S., Tan, W., Jiao, Y., Zhang, Y.C., and Shi, F., 2021. Regio- and enantioselective (3+3) cycloaddition of nitrones with 2-indolylmethanols enabled by cooperative organocatalysis. Angewandte Chemie - International Edition, 60(5), pp.2355-2363. DOI: https://doi.org/10.1002/anie.202011267 McKay, C.S., Blake, J.A., Cheng, J., Danielson, D.C., and Pezacki, J.P., 2011. Strain-promoted cycloadditions of cyclic nitrones with cyclooctynes for labeling human cancer cells. Chemical Communications, 47(36), pp.10040-10042. DOI: https://doi.org/10.1039/c1cc13808a Mohammed, J.H., and Salih, N.A.M., 2022. Synthesis and characterization of some new nitrones derivatives and screening their biological activities. Science Journal of University of Zakho, 10(4), pp.268-273. DOI: https://doi.org/10.25271/sjuoz.2022.10.4.1096 Mohammed, J.H., Qaddo, A.N.M., Salih, N.A.M., and Omar, F.B., 2023. The synthesis of some imine derivatives via condensation reactions between some aromatic phenylhydroxylamine derivatives with glyoxylic acid and the study of their biological activity. Tikrit Journal of Pure Science, 28(6), pp.34-41. DOI: https://doi.org/10.25130/tjps.v28i6.1411 Murahashi, S.I., and Imada, Y., 2019. Synthesis and transformations of nitrones for organic synthesis. Chemical Reviews, 119(7), 4684-4716. DOI: https://doi.org/10.1021/acs.chemrev.8b00476 Qaddo, A.N.M., and Abed, A.A., 2022. Heterocyclic synthesis of some new isoxazolidine derivatives via 1,3-dipolar cycloaddition of nitrones to styrene. Iraqi Journal of Science, 63(10), pp.4175-4184. DOI: https://doi.org/10.24996/ijs.2022.63.10.4 Sandmeier, T., and Carreira, E.M., 2021. Enantioselective synthesis of cyclic nitrones by chemoselective intramolecular allylic alkylation of oximes. Angewandte Chemie - International Edition, 60(18), pp.9913-9918. DOI: https://doi.org/10.1002/anie.202100150 Yang, X., Cheng, F., Kou, Y.D., Pang, S., Shen, Y.C., Huang, Y.Y., and Shibata, N., 2017. Catalytic asymmetric 1,3-dipolar cycloaddition of β-fluoroalkylated α,β-unsaturated 2-pyridylsulfones with nitrones for chiral fluoroalkylated isoxazolidines and γ-amino alcohols. Angewandte Chemie, 129(6), pp.1532-1536. DOI: https://doi.org/10.1002/ange.201610605
Uncontrolled Keywords:	Aromatic oximes, Azomethine-N-oxide, Biological activity, Condensation reaction
Subjects:	Q Science > QD Chemistry
Divisions:	ARO-The Scientific Journal of Koya University > VOL 12, NO 1 (2024)
Depositing User:	Dr Salah Ismaeel Yahya
Date Deposited:	02 Sep 2024 06:57
Last Modified:	02 Sep 2024 06:57
URI:	http://eprints.koyauniversity.org/id/eprint/465

Actions (login required)

View Item