Antioxidant and Antimicrobial Activity of New Amide Compounds Containing Azo Group Using Dicyclohexylcarbodiimide (DCC) as Coupling Agent

Dania Mohammed Saleh; Bushra Kamel Al-Salami

doi:10.22146/ijc.92305

Antioxidant and Antimicrobial Activity of New Amide Compounds Containing Azo Group Using Dicyclohexylcarbodiimide (DCC) as Coupling Agent

https://doi.org/10.22146/ijc.92305

Dania Mohammed Saleh⁽¹⁾, Bushra Kamel Al-Salami^(2*)

(1) Department of Chemistry, College of Science, University of Basrah, P.O. Box 781, Basrah, Iraq
(2) Department of Chemistry, College of Science, University of Basrah, P.O. Box 781, Basrah, Iraq
(*) Corresponding Author

Abstract

A series of amide compounds (A2D1-A2D6) were synthesized based on sulfathiazole by converting it to diazonium salt using NaNO₂ and concentrated HCl via diazotization reaction. This reaction was followed by coupling reaction with vanillic acid in alkaline medium to generated azo compound 4-hydroxy-3-methoxy-5-((4-(N-(thiazol-2-yl)sulfamoyl)phenyl)diazenyl)-benzoic acid (A2). Compound A2 was reacted with substituted aromatic amines such as 2-amino-4,6-dimethylpyridine, sulfamerazine, sulfadiazine, sulfanilamide, sulfathiazole, and sulfanilic acid to form corresponding amides using DCC as coupling reagent to be promoted condensation reaction. The structures of synthesized compounds have been diagnosed with elemental analysis, FTIR, ¹H-NMR, ¹³C-NMR, and mass spectrometry. The antibacterial activities for all new synthetic compounds was estimated accurately depending on selected bacteria such as Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative) using different concentrations to calculate minimum inhibition concentration. The effectiveness of inhibiting fungi was also studied against Candida albicans by agar diffusion method. Finally, the antioxidant capacities of the prepared compounds were determined by using DPPH radical scavenging method. The results of potential radical scavenging activity were given as IC₅₀. The compounds showed strong biological activity and good antioxidant activity compared with the standard substance Vitamin C.

Keywords

antimicrobial; azo; DCC; sulfathiazole; vanillic acid

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References

[1] Agudo-Álvarez, S., Díaz-Mínguez, S.S., and Benito-Arenas, R., 2024, The amide group and its preparation methods by acid-amine coupling reactions: An overview, Pure Appl. Chem., 96 (5), 691–707.

[2] Abd El-Wahab, H., Abd El-Fattah, M., El-Alfy, H.M.Z., Owda, M.E., Lin, L., and Hamdy, I., 2020, Synthesis and characterisation of sulphonamide (Schiff base) ligand and its copper metal complex and their efficiency in polyurethane varnish as flame retardant and antimicrobial surface coating additives, Prog. Org. Coat., 142, 105577.

[3] Munawar, S., Zahoor, A.F., Hussain, S.M., Ahmad, S., Mansha, A., Parveen, B., Ali, K.G., and Irfan, A., 2024, Steglich esterification: A versatile synthetic approach toward the synthesis of natural products, their analogues/derivatives, Heliyon, 10 (1), e23416.

[4] Pavlovic, B., Heubel, C., Kurz, M., Oehl, E., Waldvogel, S.R., Méndez, M., and Ruf, S., 2024, Single step synthesis of β- and γ- aryl-substituted ß- and γ-amino acid derivatives by electrochemistry, Bioorg. Med. Chem. Lett., 100, 129614.

[5] Serrano-Arias, B., Araya-Zúñiga, A., Waterhouse-Garbanzo, J., Rojas-Barrantes, Z., Arguedas-Chacón, S., and Zavaleta-Monestel, E., 2023, A comprehensive review of sulfonamide hypersensitivity: implications for clinical practice, Clin. Rev. Allergy Immunol., 65 (3), 433–442.

[6] Al-Adilee, K.J., Jawad, S.H., Kyhoiesh, H.A.K., and Hassan, H.M., 2024, Synthesis, characterization, biological applications, and molecular docking studies of some transition metal complexes with azo dye ligand derived from 5-methyl imidazole, J. Mol. Struct., 1295, 136695.

[7] Aziz, D.M., Hassan, S.A., Mamand, D.M., and Qurbani, K., 2023, New azo-azomethine derivatives: Synthesis, characterization, computational, solvatochromic UV‒Vis absorption and antibacterial studies, J. Mol. Struct., 1284, 135451.‏

[8] Al-Fregi, A.A., Al-Salami, B.K., Al-Khazragie, Z.K., and Al-Rubaie, A.Z., 2019, Synthesis, characterization and antibacterial studies of some new tellurated azo compounds, Phosphorus, Sulfur Silicon Relat. Elem., 194 (1-2), 33–38.

[9] Al-Salami, B.K., Al-Hazam, H.A., and Marich, Y.A., 2019, Reinforcement of condensation reaction using DCCI to synthesis new compounds derived from phthalyl Dl-leucine and sulfa drugs, J. Eng. Appl. Sci., 14, 10579–10588.‏

[10] Hossain, T.J., 2024, Methods for screening and evaluation of antimicrobial activity: A review of protocols, advantages, and limitations, Eur. J. Microbiol. Immunol., 14 (2), 97–115.‏

[11] Abdel-Aziz, M.S., Sediek, A.A., and Abdel-Aziem, A., 2024, Antimicrobial and molecular docking studies of 1,3,4-thiadiazole tethered sulfa-azo derivatives via hydrazono-methyl bridge, Polycyclic Aromat. Compd., In Press, Corrected Proof.‏‏‏

[12] Baba, S.A., and Malik, S.A., 2015, Determination of total phenolic and flavonoid content, antimicrobial and antioxidant activity of a root extract of Arisaema jacquemontii Blume, J. Taibah Univ. Sci., 9 (4), 449–454.

[13] Al-Khazragie, Z.K., Al-Salami, B.K., and Al-Fartosy, A.J.M., 2022, Synthesis, antimicrobial, antioxidant, toxicity and anticancer activity of a new azetidinone, thiazolidinone and selenazolidinone derivatives based on sulfonamide, Indones. J. Chem., 22 (4), 979–1001.‏‏

[14] Silverstein, R.M., Webster, F.X., Kiemle, D.J., and Bryce, D.L., 2015, Spectrometric Identification of Organic Compounds, 8^th Ed., Wiley, Hoboken, New Jersey, US.

[15] Ali, A.A., and Ali, H.A., 2024, Analytical study of some azo dyes and its medical applications, J. Kufa Chem. Sci., 3 (2), 16–30.‏

[16] Uhlemann, T., Berden, G., and Oomens, J., 2021, Preferred protonation site of a series of sulfa drugs in the gas phase revealed by IR spectroscopy, Eur. Phys. J. D, 75 (1), 23.‏

[17] Zhao, L.H., Yan, H.W., Jiang, J.S., Zhang, X., Yuan, X., Yang, Y.N., and Zhang, P.C., 2024, Effective assignment of positional isomers in dimeric shikonin and its analogs by ¹H NMR spectroscopy, Chin. Chem. Lett., 35 (5), 108863.‏

[18] Santos Oliveira, A.J.M., de Castro, R.D., Pessôa, H.L.F., Wadood, A., and de Sousa, D.P., 2019, Amides derived from vanillic acid: Coupling reactions, antimicrobial evaluation, and molecular docking, BioMed Res. Int., 2019 (1), 9209676.‏

[19] Ebrahimi, H., Hadi, J.S., and Al-Ansari, H.S., 2013, A new series of Schiff bases derived from sulfa drugs and indole-3-carboxaldehyde: Synthesis, characterization, spectral and DFT computational studies, J. Mol. Struct., 1039, 37–45.

[20] Al-Hilfi, D.A., and Jadou, B.K., 2022, Synthesis, and biological studies of new azo–azomethine compounds based on sulfathiazole and sulfadiazine, Egypt. J. Chem., 65 (5), 337–345.‏

[21] Opoku-Temeng, C., Naclerio, G.A., Mohammad, H., Dayal, N., Abutaleb, N.S., Seleem, M.N., and Sintim, H.O., 2018, N-(1,3,4-oxadiazol-2-yl)benzamide analogs, bacteriostatic agents against methicillin-and vancomycin-resistant bacteria, Eur. J. Med. Chem., 155, 797–805.

[22] Malino, A.P., Kepel, B.J., Budiarso, F.D.H., Fatimawali, F., Manampiring, A.E., and Bodhi, W., 2024, In vitro test of antioxidant activity of leilem leaf ethanol extract (Clerodendrum minahassae) using DPPH and FRAP methods, Heca J. Appl. Sci., 2 (1), 27–34.‏‏

[23] Yamauchi, M., Kitamura, Y., Nagano, H., Kawatsu, J., and Gotoh, H., 2024, DPPH measurements and structure—Activity relationship studies on the antioxidant capacity of phenols, Antioxidants, 13 (3) 309.

DOI: https://doi.org/10.22146/ijc.92305