Synthesis and characterization of histidine derived sulphonamides bearing carboxamide functionality Amarachi Chinasa Achigamonye, Uchechukwu Chris Okoro, Efeturi Abraham Onoabedje University of Nigeria Nsukka, Nigeria Sulphonamides bearing carboxamides functionality have been discovered to possess significant antimalarial and antioxidant activities. Five new drug-like histidine-derived sulphonamide derivatives bearing carboxamide functionality were synthesized and characterized. The reaction of p –toluenesulphonyl chloride (1) with histidine (2) in basic medium afforded tosylhistidine intermediate (3) which had the acid functionality subsequently amidated with various secondary amines (5a-e) to obtain the corresponding carboxamides (4a-e) in excellent yields. The chemical structures of the synthesized compounds were determined by FTIR, 1 H-NMR and 13 C-NMR spectroscopic techniques. In the FTIR spectra data for N -(3-(1 H -imidazol-4-yl)-1-oxo-1-(piperidin-1-yl)propan- 2-yl)-4-methylbenzenesulphonamide (4d), the peak at 3426cm -1 indicates the presence of NH functional group. For 1 H-NMR, the signal at δ: 8.2, indicates the presence of NH-SO 2 functional group whereas for 13 C-NMR, the absorption at δ: 133.27 depicts the presence of CH=N group. References 1. Cheng, J. H., Huang, A. M., Hour, T. C., Yang, S. C., Pu, Y. S., & Lin, C. N. (2011). Antioxidant xanthone derivatives induce cell cycle arrest and apoptosis and enhance cell death induced by cisplatin in NTUB1 cells associated with ROS. European journal of medicinal chemistry , 46 (4), 1222-1231. 2. Stefoska-Needham, A., Beck, E., Johnson, S. & Tapsell L. (2015). Sorghum: An underutilized cereal whole grain with the potential to assist in the prevention of chronic disease. Food Rev. Int. 31: 401-437. 3. Sinha, S., Sarma, P., Sehgal, R & Medhi B (2017). Development in assay methods for in vitro antimalarial drug efficacy testing: A systematic review. Frontiers in Pharmacology , 8, 754. doi: 10.3389/fphar.2017.00754 4. Perlovich, G.L., Strakhova, N.N., Kazachenko, V.P., Volkova, T.V., Tkacher, V.V., Schaper, K.J. & Raevsky, O.A. (2008). Sulphonamides as subject to study molecular interactions in crystals and solution; sublimation, solubility, salvation, distribution and crystal structure. International J. Pharm. 349 (1-2), 300-313. 5. Meşeli, T., Doğan, Ş. D., Gündüz, M. G., Kökbudak, Z., Bogojevic, S. S., Noonan, T., ... & Nikodinovic-Runic, J. (2021). Design, synthesis, antibacterial activity evaluation and molecular modeling studies of new sulfonamides containing a sulfathiazole moiety.New Journal of Chemistry,45(18), 8166-8177. 6. Al-Sanea, M. M., Elkamhawy, A., Paik, S., Bua, S., Lee, S. H., Abdelgawad, M. A., Roh, E.J., Eldehna, W. M. & Supuran, C.T. (2019). Synthesis and biological evaluation of novel 3-(quinolin-4-ylamino)benzenesulphonamidesAQ3 as carbonic anhydrase isoforms I and II inhibitors, Journal of Enzyme Inhibition and Medicinal Chemistry, 34:1, 1457-1464, doi: 10.1080/14756366.2019.1652282. 7. Egbujor M. C., Okoro, U. C., Udeh, C.M., Anieze, E.O., Amadi, U. B., Okenwa-Ani, C.G. & Chidebelu, I. C. (2020). Synthesis and characterization of benzoylated sulfamoyl carboxylic acids. MOJ Biorg Org Chem, 4 (1), 22‒25. 8. Ali, A., Ali, A., Bakht, M. A. & Ahsan, M. J. (2021). Ultrasound promoted synthesis of N -(substituted phenyl)-2-(7–hydroxy- 4-methyl-2 H -chromen-2-ylidene)hydrazine-1-carboxamides as cytotoxic and antioxidant agents. Journal of Molecular Structure 1238, 130452 . https://doi.org/10.1016/j.molstructure 130452, 0022-2860.
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