Molecular Docking, Synthesis, Characterization and biological activity of new Azo-Schiff bases derivative

Mohammed Dheyaa Al-Ameedee

doi:10.32947/ajps.v25i4.1254

Authors

Mohammed Dheyaa Al-Ameedee Department of Pharmaceutical Chemistry, College of Pharmacy, Mustansiriyah University, Baghdad, Iraq

DOI:

https://doi.org/10.32947/ajps.v25i4.1254

Keywords:

Schiff bases, molecular docking, anticancer, antibacterial, antifungal

Abstract

In this study, four Schiff base derivatives (S1-S4) were designed, synthesized and tested for biological activity. The synthesized compounds were analysed and described based on their physical and chemical properties, as well as through the use of NMR and FTIR techniques. The molecular docking investigation demonstrated the potential biological action of these molecules. The results demonstrated that these compounds exhibit antibacterial, antifungal, and anticancer properties. Compound S1 and S2 exhibited antibacterial efficacy against Staphylococcus aureus and Escherichia coli. Compounds S3 and S4 exhibited fungicidal properties against Aspergillus niger and Chaladra corda. Compound S3 demonstrated significant anticancer efficacy against breast cancer, as confirmed by MTT tests.

References

1- Dadgostar, P. Antimicrobial resistance: implications and costs. Infection and drug resistance 2019, 3903-3910.

2- Morrison, L., Zembower, T. R. Antimicrobial resistance. Gastrointestinal Endoscopy Clinics 2020, 30 (4), 619-635.

3- Tang, K. W. K., Millar, B. C., Moore, J. E. Antimicrobial resistance (AMR). British Journal of Biomedical Science 2023, 80, 11387.

4- Cui, W., Aouidate, A., Wang, S., Yu, Q., Li, Y., Yuan, S. Discovering anti-cancer drugs via computational methods. Frontiers in pharmacology 2020, 11, 733.

5- Kumar, R., Singh, A. A., Kumar, U., Jain, P., Sharma, A. K., Kant, C., & Faizi, M. S. H. Recent advances in synthesis of heterocyclic Schiff base transition metal complexes and their antimicrobial activities especially antibacterial and antifungal. Journal of Molecular Structure 2023, 1294, 136346.‏

6- Ceramella, J., Iacopetta, D., Catalano, A., Cirillo, F., Lappano, R., Sinicropi, M. S. A review on the antimicrobial activity of Schiff bases: Data collection and recent studies. Antibiotics 2022, 11 (2), 191.

7- Ibrahim, D.M., Ali, K.F. and Abd_alwahab, M.H. Synthesis and antimicrobial evaluation of Histidine Cinnamaldehyde Schiff base containing structural feature of 1, 3, 4-thiadiazole heterocyclic moiety. Al Mustansiriyah Journal of Pharmaceutical Sciences 2020, 20(1), pp.1-12.

8- Hamad, A., Chen, Y., Khan, M. A., Jamshidi, S., Saeed, N., Clifford, M., Hind, C., Sutton, J. M., Rahman, K. M. Schiff bases of sulphonamides as a new class of antifungal agent against multidrug‐resistant Candida auris. MicrobiologyOpen 2021, 10 (4), e1218.

9- Kaushik, S., Paliwal, S. K., Iyer, M. R., Patil, V. M. Promising Schiff bases in antiviral drug design and discovery. Medicinal Chemistry Research 2023, 32 (6), 1063-1076.

10- Imparato, R., Rosa, N., De Bernardo, M. Antiviral drugs in adenovirus-induced keratoconjunctivitis. Microorganisms 2022, 10 (10), 2014.

11- Mahdi, M.F. and Raauf, A.M. Molecular modelling, Synthesis and Antiproliferative Evaluation of New Phenyldiazenyl)-Pyrazol Schiff Base Derivatives. Al Mustansiriyah Journal of Pharmaceutical Sciences. 2024, 24(1), pp.25-37.

12- Uddin, N., Rashid, F., Ali, S., Tirmizi, S. A., Ahmad, I., Zaib, S., Zubair, M., Diaconescu, P. L., Tahir, M. N., Iqbal, J. Synthesis, characterization, and anticancer activity of Schiff bases. Journal of Biomolecular Structure and Dynamics 2020, 38 (11), 3246-3259.

13- Wang, Y.-E., Yang, D., Huo, J., Chen, L., Kang, Z., Mao, J., Zhang, J. Design, synthesis, and herbicidal activity of thioether containing 1, 2, 4-triazole schiff bases as transketolase inhibitors. Journal of Agricultural and Food Chemistry 2021, 69 (40), 11773-11780.

14- Pervaiz, M., Sadiq, S., Sadiq, A., Younas, U., Ashraf, A., Saeed, Z., Zuber, M., Adnan, A. Azo-Schiff base derivatives of transition metal complexes as antimicrobial agents. Coordination Chemistry Reviews 2021, 447, 214128.

15- Muhammed Aziz, D., Hassan, S. A., Mamand, D. M., Qurbani, K. New azo-azomethine derivatives: Synthesis, characterization, computational, solvatochromic UV‒Vis absorption and antibacterial studies. Journal of Molecular Structure 2023, 1284, 135451.

16- Muhammad-Ali, M. A., Qanber Jasim, E., H. Al-Saadoon, A. Synthesis, Antibacterial Evaluation, and Docking Studies of Some Azo Compounds and Schiff Bases Derived from Sulfonamide. Journal of Medicinal and Chemical Sciences 2023, 6 (9), 2128-2139. doi: 10.26655/jmchemsci.2023.9.19.

17- Nikokar, I., Ebrahim-Saraie, H.S. and Ganjian, H. Variations in antibiotic susceptibility profile of Staphylococcus aureus after povidone-iodine stress. Pharmaceutical Sciences 2016, 23(1), pp.72-76.

18- Aditi, F.Y., Rahman, S.S. and Hossain, M.M. A study on the microbiological status of mineral drinking water. The Open Microbiology Journal 2017, 11, p.31.

19- Tokarzewski, S., Ziółkowska, G. and Nowakiewicz, A. Susceptibility testing of Aspergillus niger strains isolated from poultry to antifungal drugs-a comparative study of the disk diffusion, broth microdilution (M 38-A) and Etest® methods. Polish journal of veterinary sciences 2012;15(1):125-33.

20- Moges, B., Bitew, A. and Shewaamare, A. Spectrum and the in vitro antifungal susceptibility pattern of yeast isolates in Ethiopian HIV patients with oropharyngeal candidiasis. International journal of microbiology 2016(1), p.3037817.

21- El-Tabl, A. S., Abd-El Wahed, M.M., Shakdofa, M.M., Wahba, M.A. and Shakdofa, A.M. AzoSchiff base complexes synthesis, spectroscopic characterization and microbicide studies. Journal of Chemistry and Chemical Sciences 2017, 7 (3), 170-191.

22- Hashim, D., J., Saad, M. M. Preparation, Characterization, and Biological Study of New Halogenated Azo-Schiff Base Ligands and Their Complexes. Journal of Medicinal and Chemical Sciences 2022, 6 (7), 1555-1576. doi: 10.26655/jmchemsci.2023.7.8.

23- Lather, A., Sharma, S., Khatkar, A. Aesculin based glucosamine-6-phosphate synthase inhibitors as novel preservatives for food and pharmaceutical products: in-silico studies, antimicrobial and preservative efficacy evaluation. BMC chemistry 2021, 15, 1-11.

24- Lather, A., Sharma, S., Khatkar, A. Naringin derivatives as glucosamine-6-phosphate synthase inhibitors-based preservatives and their biological evaluation. Scientific Reports 2020, 10 (1), 20477.

25- Zhong, Y., Han, X., Li, S., Qi, H., Song, Y., Qiao, X. Design, synthesis, antifungal activity and molecular docking of thiochroman-4-one derivatives. Chemical and Pharmaceutical Bulletin 2017, 65 (10), 904-910.