Heterocyclic Azo Compounds, Synthesis, Characterization, Evaluation as Antimicrobial, and Theoretical Study
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Keywords:
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Azo Compounds, Antimicrobial, DFT, Molecular Docking
Abstract
Five azo compounds, including N-(3-hydroxyphenyl) maleimide, were synthesized and characterized using FT-IR, 1H-NMR, 13C-NMR, and mass spectroscopy. The compounds were evaluated for antibacterial activity against Staphylococcus aureus and Pseudomonas aeruginosa using the disk diffusion method. The screening results showed that the azo compounds tested were effective against the bacteria tested, particularly Staphylococcus aureus. The geometry optimization of the molecular structures and the energy calculations for compounds 1-5 were performed using the density functional approach. Molecular docking was conducted to examine the interaction of the synthesized compound 1 with two bacterial receptors and one viral receptor (neuraminidase). It was found that they would target the PDB:4CJN protein, for which the compound yielded the lowest binding energy.
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Piotto, S., S. Concilio, L. Sessa, R. Diana, G. Torrens, C. Juan, U. Caruso, and P. Iannelli (2017). Synthesis and Antimicrobial Studies of New Antibacterial Azo-Compounds Active against Staphylococcus aureus and Listeria monocytogenes. Molecules, 22(8); 1372
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Rabel, M. and R. Prabhath (2015). A Study of the Structure-Property Relationship of Azole-Azine Based Homoleptic Platinum(II) Complexes and Tunability of the Photo-Physical Properties. University of Surrey (United Kingdom)
Scarim, C. B. and C. M. Chin (2021). The Use of Heterocyclic-Based Azo Compounds Bearing Pyrrolidine, Imidazole, Triazole, and Thiazole Moieties for the Treatment of Neglected Tropical Disease Caused by Schistosoma mansoni. European Journal of Medicinal Chemistry Reports, 1; 100001
Shafeeq, A. A., Z. Mohammed, A. Hamandi, M. H. Mohammed, and G. Al-Shamma (2023). Synthesis, Characterization, and Antimicrobial Evaluation for New Azo-Linked Derivative of Heterocyclic Compounds. Journal of Contemporary Medical Sciences, 8(1); 51–58
Temma, A. S., O. N. Ali, R. H. Al-Asadi, and M. K. Mohammed (2025). Evaluation of Schiff Bases Against Two Cancer Cell Lines: A Combined Experimental and Theoretical Approach. Tropical Journal of Natural Product Research, 9(3); 967–972
Upadhayay, A., J. Ling, D. Pal, Y. Xie, F.-F. Ping, and A. Kumar (2023). Resistance-Proof Antimicrobial Drug Discovery to Combat Global Antimicrobial Resistance Threat. Drug Resistance Updates, 66; 100890
Widjajanti, H., C. V. Handayani, and E. Nurnawati (2021). Antibacterial Activity of Endophytic Fungi from Sembukan (Paederia foetida L.) Leaves. Science and Technology Indonesia, 6(3); 189–195
Wiegand, I., K. Hilpert, and R. E. W. Hancock (2008). Agar and Broth Dilution Methods to Determine the Minimal Inhibitory Concentration (MIC) of Antimicrobial Substances. Nature Protocols, 3(2); 163–175
Al-Ameertaha, A. R. and R. H. Al-Asadi (2025). Design, Synthesis, Characterization, DFT, Molecular Docking Studies and Evaluation of Biological Activity of Benzamidethiourea Derivatives against HepG2 Hepatocellular Carcinoma Cell Lines. Advanced Journal of Chemistry, Section A, 8(2); 220–244
Al-Asadi, R. H. (2019). Synthesis, DFT Calculation and Biological Activity of Some Organotellurium Compounds Containing Azomethine Group. Orbital, 11(7); 402–410
Al-Asadi, R. H., M. K. Mohammed, and H. K. Dhaef (2020). Mercuration and Telluration of 2-Fluoro-5-nitroaniline: Synthesis, Antibacterial, and Computational Study. Russian Journal of General Chemistry, 90(4); 703–709
Al-Resayes, S. I., A. J. Jarad, J. M. M. Al-Zinkee, T. H. Al-Noor, M. M. El-Ajaily, M. Abdalla, K. Min, M. Azam, and R. K. Mohapatra (2023). Synthesis, Characterization, Antimicrobial Studies, and Molecular Docking Studies of Transition Metal Complexes Formed from a Benzothiazole-Based Azo Ligand. Bulletin of the Chemical Society of Ethiopia, 37(4); 931–944
Al-Salim, Y. M. and R. H. Al-Asadi (2023). Synthesis, Antibreast Cancer Activity, and Molecular Docking Studies of Thiourea Benzamide Derivatives and Their Complexes with Copper Ion. Tropical Journal of Natural Product Research, 7(6); 3158–3167
Ali, Y., N. Muhamad Bunnori, D. Susanti, A. Muhammad Alhassan, and S. Abd Hamid (2018). Synthesis, In-Vitro and In Silico Studies of Azo-Based Calix[4]arenes as Antibacterial Agent and Neuraminidase Inhibitor: A New Look Into an Old Scaffold. Frontiers in Chemistry, 6; 210
Dhaef, H. K., R. H. Al-Asadi, A. A. Shenta, and M. K. Mohammed (2021). Novel Bis Maleimide Derivatives Containing Azo Group: Synthesis, Corrosion Inhibition, and Theoretical Study. Indonesian Journal of Chemistry, 21(5); 1212–1220
Elsayed, E. H., D. Al-Wahaib, A. E. D. Ali, B. A. Abd-El-Nabey, and H. A. Elbadawy (2023). Synthesis, Characterization, DNA Binding Interactions, DFT Calculations, and Covid-19 Molecular Docking of Novel Bioactive Copper(I) Complexes Developed via Unexpected Reduction of Azo-Hydrazo Ligands. BMC Chemistry, 17(1); 159
Falah Azeez, Z., L. Ali Khaleel, and H. Ali Kadhim Kyhoiesh (2024). Synthesis, Biological Evaluation, Molecular Docking Analyses, and ADMET Study of Azo Derivatives Containing 1-Naphthol against M????L-Producing S. maltophilia. Results in Chemistry, 12; 101864
Hamdani, S. S., B. A. Bhat, L. Tariq, S. I. Yaseen, I. Ara, B. Rafi, S. N. Hamdani, T. Hassan, and O. Rashid (2020). Antibiotic Resistance: The Future Disaster. International Journal for Research in Applied Sciences and Biotechnology, 7; 101864
Irminova, S., B. Sezgin, and T. Tilki (2020). Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations. Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi, 15(2); 319–329
Jarallah, H. M., H. K. Dhaef, M. K. Mohammed, S. M. H. Ismal, and A. A. Hussein (2026). Synthesis, Characterization of Novel Azo Compounds as Corrosion Inhibitors for Carbon Steel in HCl, and Their Theoretical Study. Science and Technology Indonesia, 11(1); 84–95
Jasim, E. Q., M. A. Muhammad-Ali, and A. Almakki (2023). Synthesis, Characterization, and Antibacterial Activity of Some Mesalazine Derivatives. Science and Technology Indonesia, 8(3); 338–343
Marinescu, M., C. V. Popa, M. A. Tănase, A. C. Soare, C. Tablet, D. Bala, L. O. Cinteza, L. M. Diţu, I. C. Gifu, and C. Petcu (2022). Synthesis, Characterization, DFT Study and Antifungal Activities of Some Novel 2-(Phenyldiazenyl)Phenol Based Azo Dyes. Materials, 15(22); 8162
Mohammed, M. K., F. A. Almasha, H. H. Al-Hujaj, R. H. Al-Asadi, H. A. Jaber, A. M. Jassem, and H. K. Dhaef (2024). Synthesis, Characterization, Cytotoxic Evaluation on MCF-7 Breast Cancer Cells, and Theoretical Studies of Novel 1,2,3-Triazoles. Tropical Journal of Natural Product Research, 8(10); 8788–8795
Morrison, J. J., V. K. Brandt, and S. G. Yeates (2019). Comment on: Synthesis of New Azo Compounds Based on N-(4-Hydroxyphenyl)maleimide and N-(4-Methylphenyl)maleimide. Molecules, 24(12); 2319
Mutlaq, D., A. Al-Shawi, and R. Al-Asadi (2021). Synthesis, Characterization, Anticancer Activity, and Molecular Docking of Novel Maleimide-Succinimide Derivatives. Egyptian Pharmaceutical Journal, 20(4); 303–312
Osman, O. I. (2017). DFT Study of the Structure, Reactivity, Natural Bond Orbital and Hyperpolarizability of Thiazole Azo Dyes. International Journal of Molecular Sciences, 18(2); 239
Piotto, S., S. Concilio, L. Sessa, R. Diana, G. Torrens, C. Juan, U. Caruso, and P. Iannelli (2017). Synthesis and Antimicrobial Studies of New Antibacterial Azo-Compounds Active against Staphylococcus aureus and Listeria monocytogenes. Molecules, 22(8); 1372
Prakash, S., G. Somiya, N. Elavarasan, K. Subashini, S. Kanaga, R. Dhandapani, M. Sivanandam, P. Kumaradhas, C. Thirunavukkarasu, and V. Sujatha (2021). Synthesis and Characterization of Novel Bioactive Azo Compounds Fused with Benzothiazole and Their Versatile Biological Applications. Journal of Molecular Structure, 1224; 129016
Rabel, M. and R. Prabhath (2015). A Study of the Structure-Property Relationship of Azole-Azine Based Homoleptic Platinum(II) Complexes and Tunability of the Photo-Physical Properties. University of Surrey (United Kingdom)
Scarim, C. B. and C. M. Chin (2021). The Use of Heterocyclic-Based Azo Compounds Bearing Pyrrolidine, Imidazole, Triazole, and Thiazole Moieties for the Treatment of Neglected Tropical Disease Caused by Schistosoma mansoni. European Journal of Medicinal Chemistry Reports, 1; 100001
Shafeeq, A. A., Z. Mohammed, A. Hamandi, M. H. Mohammed, and G. Al-Shamma (2023). Synthesis, Characterization, and Antimicrobial Evaluation for New Azo-Linked Derivative of Heterocyclic Compounds. Journal of Contemporary Medical Sciences, 8(1); 51–58
Temma, A. S., O. N. Ali, R. H. Al-Asadi, and M. K. Mohammed (2025). Evaluation of Schiff Bases Against Two Cancer Cell Lines: A Combined Experimental and Theoretical Approach. Tropical Journal of Natural Product Research, 9(3); 967–972
Upadhayay, A., J. Ling, D. Pal, Y. Xie, F.-F. Ping, and A. Kumar (2023). Resistance-Proof Antimicrobial Drug Discovery to Combat Global Antimicrobial Resistance Threat. Drug Resistance Updates, 66; 100890
Widjajanti, H., C. V. Handayani, and E. Nurnawati (2021). Antibacterial Activity of Endophytic Fungi from Sembukan (Paederia foetida L.) Leaves. Science and Technology Indonesia, 6(3); 189–195
Wiegand, I., K. Hilpert, and R. E. W. Hancock (2008). Agar and Broth Dilution Methods to Determine the Minimal Inhibitory Concentration (MIC) of Antimicrobial Substances. Nature Protocols, 3(2); 163–175
Authors
Mohammed, M. K. ., Al-Jaber, A. A. ., Al-Asadi, R. H. ., & Dhaef, H. K. . (2026). Heterocyclic Azo Compounds, Synthesis, Characterization, Evaluation as Antimicrobial, and Theoretical Study. Science and Technology Indonesia, 11(2), 489–501. https://doi.org/10.26554/sti.2026.11.2.489-501
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