Synthesis and Characterization of Heterocyclic Compounds from Natural Carboxylic Acids: Evaluation of Their Antioxidant and Biological Activities
Keywords:
Heterocyclic compounds, Benzimidazole derivatives, Antioxidant activity, Antibacterial activity, Natural carboxylic acids
Abstract
Heterocyclic compounds derived from natural carboxylic acids have gained significant attention for their biological activities, yet their potential remains underexplored. This study focuses on the synthesis of benzimidazole derivatives (Z1-Z6) using adipic, citric, salicylic, oleic, tartaric, and hydroxy acetic acids with o-phenylenediamine. Characterization was conducted using FTIR and NMR spectroscopy. Antioxidant activity was evaluated in vitro via the DPPH assay, revealing significant scavenging activity for Z2 and Z4. Antibacterial activity against Staphylococcus aureus was assessed for Z3 and Z6 using the agar diffusion method, showing maximum inhibition zones of 22–24 mm at 800 µg/mL. These findings highlight the potential of these compounds as antioxidants and antibacterial agents, offering promising leads for further pharmaceutical development.
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References
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[2] J. A. Kanters, J. Kroon, A. F. Peerdeman, and J. C. Schoone, “Conformation of Some Carboxylic Acids and Their Derivatives,” Tetrahedron, vol. 23, no. 10, pp. 4027–4033, Jan. 1967.
[3] W. Yan et al., “Recent Progress in Adipic Acid Synthesis Over Heterogeneous Catalysts,” Frontiers in Chemistry, vol. 8, p. 185, Mar. 2020.
[4] A. Amato, A. Becci, and F. Beolchini, “Citric Acid Bioproduction: The Technological Innovation Change,” Critical Reviews in Biotechnology, vol. 40, pp. 199–212, 2020.
[5] W. Hu, W. J. Li, H. Q. Yang, J. Chen, and J. Hong, “Current Strategies and Future Prospects for Enhancing Microbial Production of Citric Acid,” Applied Microbiology and Biotechnology, vol. 103, pp. 201–209, 2019.
[6] K. Bano, B. Kumar, M. N. Alyemeni, and P. Ahmad, “Exogenously-Sourced Salicylic Acid Imparts Resilience Towards Arsenic Stress by Modulating Photosynthesis, Antioxidant Potential, and Arsenic Sequestration in Brassica Napus Plants,” Antioxidants, vol. 11, no. 10, p. 2010, Oct. 2022.
[7] S. Singh, “Salicylic Acid Elicitation Improves Antioxidant Activity of Spinach Leaves by Increasing Phenolic Content and Enzyme Levels,” Food Chemistry Advances, vol. 2, p. 100156, 2023.
[8] I. Pravst, “Oleic Acid and Its Potential Health Effects,” Oleic Acid: Production, Uses and Potential Health Effects, pp. 35–54, 2014.
[9] Y. Lu et al., “Protective Effects of Oleic Acid and Polyphenols in Extra Virgin Olive Oil on Cardiovascular Diseases,” Food Science and Human Wellness, vol. 13, no. 2, pp. 529–540, Mar. 2024.
[10] M. Li et al., “Grape Tartaric Acid: Chemistry, Function, Metabolism, and Regulation,” Horticulturae, vol. 9, no. 11, p. 1173, Oct. 2023.
[11] D. B. Jack, “One Hundred Years of Aspirin,” The Lancet, vol. 350, no. 9075, pp. 437–439, Aug. 1997.
[12] X. Wang, “A Theory for the Mechanism of Action of the α-Hydroxy Acids Applied to the Skin,” Medical Hypotheses, vol. 53, no. 5, pp. 380–382, Nov. 1999.
[13] K. F. Ansari and C. Lal, “Synthesis, Physicochemical Properties and Antimicrobial Activity of Some New Benzimidazole Derivatives,” European Journal of Medicinal Chemistry, vol. 44, no. 10, pp. 4028–4033, Oct. 2009.
[14] S. Dixit, P. K. Sharma, and N. Kaushik, “Synthesis of Novel Benzimidazole Derivatives: As Potent Analgesic Agent,” Medicinal Chemistry Research, vol. 22, pp. 900–904, Feb. 2013.
[15] O. O. Ajani et al., “Facile Synthesis, Characterization and Antimicrobial Activity of 2-Alkanamino Benzimidazole Derivatives,” Oriental Journal of Chemistry, vol. 32, no. 1, p. 109, 2016.
[16] M. Okawa, J. Kinjo, T. Nohara, and M. Ono, “DPPH (1,1-Diphenyl-2-Picrylhydrazyl) Radical Scavenging Activity of Flavonoids Obtained from Some Medicinal Plants,” Biological and Pharmaceutical Bulletin, vol. 24, no. 10, pp. 1202–1205, 2001.
[17] H. H. Bahjat, R. A. Ismail, G. M. Sulaiman, and M. S. Jabir, “Magnetic Field-Assisted Laser Ablation of Titanium Dioxide Nanoparticles in Water for Anti-Bacterial Applications,” Journal of Inorganic and Organometallic Polymers and Materials, vol. 31, no. 9, pp. 3649–3656, Sep. 2021.
[18] K. S. Khashan et al., “Anticancer Activity and Toxicity of Carbon Nanoparticles Produced by Pulsed Laser Ablation of Graphite in Water,” Advances in Natural Sciences: Nanoscience and Nanotechnology, vol. 11, no. 3, p. 035010, Jul. 2020.
[19] K. S. Khashan et al., “Antibacterial Activity of Zinc Oxide Nanostructured Materials Synthesized by Laser Ablation Method,” Journal of Physics: Conference Series, vol. 1795, no. 1, p. 012040, Mar. 2021.
[20] M. A. Jihad et al., “Polyethylene Glycol Functionalized Graphene Oxide Nanoparticles Loaded with Nigella Sativa Extract: A Smart Antibacterial Therapeutic Drug Delivery System,” Molecules, vol. 26, no. 11, p. 3067, May 2021.
[21] M. K. Mohammed et al., “Functionalization, Characterization, and Antibacterial Activity of Single-Wall and Multi-Wall Carbon Nanotubes,” IOP Conference Series: Materials Science and Engineering, vol. 757, no. 1, p. 012028, Mar. 2020.
[22] E. M. Emily, Fourier Transform Infrared Spectroscopy (FTIR): Methods, Analysis and Research Insights, Chemical Engineering Methods and Technology, pp. 55–57, 2016.
[23] L. Peplowski et al., “Vibrational Spectroscopy Studies of Methacrylic Polymers Containing Heterocyclic Azo Dyes,” Vibrational Spectroscopy, vol. 120, p. 103377, May 2022.
[24] F. Elmi et al., “Application of FT-IR Spectroscopy on Breast Cancer Serum Analysis,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 187, pp. 87–91, Dec. 2017.
[25] N. Sreejayan and M. N. Rao, “Free Radical Scavenging Activity of Curcuminoids,” Arzneimittel-Forschung, vol. 46, no. 2, pp. 169–171, Feb. 1996.
[26] Q. Liu et al., “Antioxidant Activities, Phenolic Profiles, and Organic Acid Contents of Fruit Vinegars,” Antioxidants, vol. 8, no. 4, p. 78, Mar. 2019.
[27] I. H. Ali et al., “Pathological and Immunological Study on Infection with Escherichia coli in Ale BALB/C Mice,” Journal of Physics: Conference Series, vol. 1003, p. 012009, May 2018.
[28] X. Song et al., “Antibacterial Effect and Possible Mechanism of Salicylic Acid Microcapsules Against Escherichia coli and Staphylococcus aureus,” International Journal of Environmental Research and Public Health, vol. 19, no. 19, p. 12761, Oct. 2022.
Published
2024-12-05
How to Cite
Mohammad, Z. H. (2024). Synthesis and Characterization of Heterocyclic Compounds from Natural Carboxylic Acids: Evaluation of Their Antioxidant and Biological Activities. Central Asian Journal of Theoretical and Applied Science, 5(8), 672-684. Retrieved from https://cajotas.casjournal.org/index.php/CAJOTAS/article/view/1521
Section
Articles
This work is licensed under a Creative Commons Attribution 4.0 International License.
