Synthesis, Spectroscopic study and Biological activity of some New Heterocyclic compounds derived from Sulfadiazine

  • Sangar A. Hassan Department of Chemistry, College of Science, University of Raparin, Sulaimanyah, Kurdistan Region, Iraq
  • Media Noori Abdullah Department of Chemistry, College of Science, Salahaddin University-Erbil, Kurdistan Region, Iraq
Keywords: Sulfadiazine, β-lactam, Pyrrolone, Antioxidant, Antibacterial


This study illustrates the synthesis and spectroscopic study of new β-lactam and novel Pyrrolone derivatives with the study of their antioxidant and antibacterial activities. This study included two major steps, the first step involved the synthesis of imine derivatives (3a-j) from sulfadiazine. The second step contained the synthesis of 2-Azetidinone (4a-j) and Pyrrolone (5a-j) heterocyclic compounds that have been generated through the reaction between synthesized imine derivatives with chloroacetyl chloride and fumaryl chloride in the presence of triethylamine, respectively. The structures of the synthesized compounds were confirmed on the basis of their spectral data such as FT-IR, 1H-NMR and 13C-NMR spectra, which provided the expected frequencies and signals. Lastly, all products were screened for the antioxidant activity and against two kinds of bacteria Staphylococcus aureus G (+ve) and Escherichia coli G (-ve) microorganisms. The products showed lower to high antioxidant activity as compared to standard ascorbic acid. Some of the products evaluated inactive and others slight to high activity against both kinds of bacteria.

Author Biography

Media Noori Abdullah, Department of Chemistry, College of Science, Salahaddin University-Erbil, Kurdistan Region, Iraq

Science \ Chemistry


ABDULSADA, A. H., NASSER, N. H. & HUSSEIN, A. K. 2018. Synthesis and Preliminary Antibacterial Evaluation of Schiff Base Metal Complexes of Ampicillin and Cephalexin. Acta Chimica and Pharmaceutica Indica, 8, 123
ADAM, R. W. 2018. Synthesis and Characterization of some New synthesis of N-(pyrimidin-2-yl) benzenesulfonamide derivatives combined with oxaimidizolidine. Journal of Pharmaceutical Sciences and Research, 10, 3103.
AL-MULLA, A. 2017. A review: biological importance of heterocyclic compounds. Der Pharma Chemica, 9, 141-1472.
ALI, Y., ALAMA, M. S., HAMIDA, H. & HUSSAIN, A. 2014. 2 (3h) pyrrolone–a biologically active scaffold (a review). Oriental Journal of Chemistry, 30, 01-16.
ARYA, N., JAGDALE, A. Y., PATIL, T. A., YERAMWAR, S. S., HOLIKATTI, S. S., DWIVEDI, J., SHISHOO, C. J. & JAIN, K. S. 2014. The chemistry and biological potential of azetidin-2-ones. European journal of medicinal chemistry, 74, 619-656.
BÖHM, M., MORANO, I., PIESKE, B., RÜEGG, J., WANKERL, M., ZIMMERMANN, R. & ERDMANN, E. 1991. Contribution of cAMP-phosphodiesterase inhibition and sensitization of the contractile proteins for calcium to the inotropic effect of pimobendan in the failing human myocardium. Circulation research, 68, 689-701.
DA SILVA, C. M., DA SILVA, D. L., MODOLO, L. V., ALVES, R. B., DE RESENDE, M. A., MARTINS, C. V. & DE FÁTIMA, Â. 2011. Schiff bases: A short review of their antimicrobial activities. Journal of Advanced research, 2, 1-8.
EL-SHEHRY, M. F., ABU-ZIED, K. M., EWIES, E. F., AWAD, S. M. & MOHRAM, M. E. 2013. Synthesis of some novel azaheterocycles utilizing 3-(4-nitrobenzylidene)-5-phenylfuran-2 (3H)-one with expected antimicrobial activity. Der pharma chem, 5, 318-326.
GUPTA, A. & HALVE, A. 2015. [Beta]-LACTAMS: A MINI REVIEW OF THEIR BIOLOGICAL ACTIVITY. International Journal of Pharmaceutical Sciences and Research, 6, 978.
KUMAR, D., SINGH, A. & WALIA, Y. K. 2014. Synthesis and Characterization of 2H-Pyrrole-2-Ones of (5-Benzoyl-benzoimidazol-1-yl)-acetic acid hydrazide derivatives. Asian J. of Adv. Basic Sci, 2, 40-46.
MOHAMMED ABD AL-KHALIQ, Z. 2015. Synthesis, characterization and antibacterial activity of new series of sulfamethoxazole derivatives. Ministry of Higher Education.
NUNNA, R., RAMACHANDRAN, D., MODI, V. B. & GOSWAMI, K. J. 2014. Synthesis, Characterization and Anti Microbial Activity of Some Novel Heterocyclic Compounds Having Sulphamido Moiety. Chemical Science, 2, 00-00.
SALUNKHE, D. & PISTE, P. 2014. A brief review on recent synthesis of 2-azetidinone derivatives. Int J Pharm Life Sci, 5, 666-689.
SHAHID, M., SALIM, M., KHALID, M., TAHIR, M. N., KHAN, M. U. & BRAGA, A. A. C. 2018. Synthetic, XRD, non-covalent interactions and solvent dependent nonlinear optical studies of Sulfadiazine-Ortho-Vanillin Schiff base:(E)-4-((2-hydroxy-3-methoxy-benzylidene) amino)-N-(pyrimidin-2-yl) benzene-sulfonamide. Journal of Molecular Structure, 1161, 66-75.
SINHA, D., TIWARI, A. K., SINGH, S., SHUKLA, G., MISHRA, P., CHANDRA, H. & MISHRA, A. K. 2008. Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde. European journal of medicinal chemistry, 43, 160-165.
TAYLOR, A. P., ROBINSON, R. P., FOBIAN, Y. M., BLAKEMORE, D. C., JONES, L. H. & FADEYI, O. 2016. Modern advances in heterocyclic chemistry in drug discovery. Organic & biomolecular chemistry, 14, 6611-6637.
ZHENG, Y., MA, K., LI, H., LI, J., HE, J., SUN, X., LI, R. & MA, J. 2009. One pot synthesis of imines from aromatic nitro compounds with a novel Ni/SiO 2 magnetic catalyst. Catalysis letters, 128, 465-474.
How to Cite
A. Hassan, S., and M. Abdullah. “Synthesis, Spectroscopic Study and Biological Activity of Some New Heterocyclic Compounds Derived from Sulfadiazine”. ZANCO Journal of Pure and Applied Sciences, Vol. 31, no. 6, Dec. 2019, pp. 92-09, doi:10.21271/zjpas.31.6.10.
Biology and Medical Researches