Synthesis of Mannich N-bases based on benzimidazole derivatives using SiO2OAlCl2 catalyst and their potential as antioxidant, antibacterial, and anticancer agents
• Synthesis of SiO 2 -OAlCl 2 as eco-friendly catalyst, provides high product yield and exceptional durability, and enabling repeated use during synthesis processes. • These catalysts exhibit significant catalytic activity in the synthesis of Mannich N -bases based on benzimidazole derivatives, with yields of between 65-85 % using a 10 % mmol amount of catalyst with ethanol at room temperatures. • The antioxidant activity of Mannich N -bases based on benzimidazole derivatives compounds is assessed by DPPH tests, demonstrating their significant antioxidant properties. • The antibacterial activity of Mannich N -bases based on benzimidazole derivatives compounds is assessed by gram-positive and gram-negative bacteria tests, which demonstrated the potential of these compounds as antibacterial agents. • The anticancer activity of Mannich N -bases based on benzimidazole derivatives compounds is assessed by MTT tests with MCF-7 breast cancer cells, which demonstrated the potential of these compounds as anticancer agents. This research aimed to synthesis of N -base compounds based on benzimidazole derivatives and their potential as antibacterials, antioxidants, and anticancer. The synthesis was conducted in two stages, namely the intermediate (benzimidazole derivatives) and the final product ( N -mannich base), using five variations of organic acids and SiO 2 -OAlCl 2 as catalyst. The results showed that the catalyst was successfully synthesized and characterized by The Fourier transform infrared (FTIR), X-ray diffraction (XRD), and Scanning electron microscopy with energy dispersive X-ray spectroscopy (SEM-EDS). The purity of the synthesized compounds was monitored by Thin layer chromatography (TLC), melting point test, Ultraviolet-visible (UV-Vis), FTIR, and Liquid chromatography-Mass spectrometry (LC-MS). The five intermediate compounds and five mannich base products yield 77%-89% and 65%-85%, respectively. The final products were applied through antibacterial testing against Staphylococcus aureus (Gram-positive bacteria) and Escherichia coli (Gram-negative bacteria) by disc diffusion. Mannich base compounds have potential antibacterial agents, but only 4A and 4E gave the best inhibition zone diameter. Meanwhile, the antioxidant testing result using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) method showed the best activity in the mannich base compound 4E. The anticancer test result showed that the five mannich base compounds had potential as anticancer agents.
Authors
- Kang Hyun Park (ORCID: https://orcid.org/0000-0001-9946-0522)
- Laely Amaliyah
- Dicky Annas (ORCID: https://orcid.org/0000-0002-3838-2994)
- Mohammad Jihad Madiabu (ORCID: https://orcid.org/0000-0002-6863-665X)
- Bayu Ardiansah (ORCID: https://orcid.org/0000-0002-1664-9133)
- Antonius Herry Cahyana (ORCID: https://orcid.org/0000-0002-2613-765X)
- Inda Mapiliandari
- Aida Nadia
- Ikrimah Desta
- Hilna Diana Sahaya
Institutions
- IPB University (ID)
- University of Indonesia (ID)
- National Research and Innovation Agency (ID)
- Pusan National University (KR)
Publication Details
- Journal
- South African Journal of Chemical Engineering
- Published
- 2024-11-07
- DOI
- https://doi.org/10.1016/j.sajce.2024.11.003
- Citations
- 1
- Primary Topic
- Synthesis and biological activity
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- Direktorat Riset and Pengembangan, Universitas Indonesia