SYNTHESIS, ANTIBACTERIAL ACTIVITY AND DOCKING STUDIES OF BENZYL ALCOHOL DERIVATIVES

Year 2020, Volume: 7 Issue: 2, 481 - 488, 23.06.2020

Mamman Sulaıman Yusuf Hassan , Tugba Taskin Tok , Xavier Siwe Noundou

https://doi.org/10.18596/jotcsa.692113

Cited By: 8

Abstract

Benzyl alcohol derivatives were synthesized, and characterized using NMR and FTIR spectroscopic techniques. For the first time, the antibacterial activities of the synthesized compounds were examined using disc diffusion method by measuring the diameter of the zones of inhibition against Staphylococcus aureus and Pseudomonas aeruginosa. The results demonstrated that the activity was concentration dependant, and that the compounds were generally potent against P. aeruginosa. Only two of the compounds were active against S. aureus. In terms of broad spectrum activity, compound 2d (35 mm) was found to exhibit a promising efficacy which surpassed that of the standard drug (amoxicillin).The binding of compounds 2a-e to the glucosamine-6-phosphate synthase (GlcN-6-P) active-site revealed that all the synthesized compounds fitted into the GlcN-6-P active-site receptor cavity, exhibited potential hydrogen-bonding interactions with the proximal amino acid residues and aligned similar to amoxicillin. Interestingly, it has been found that the most active compound, 2d also appeared to have a relatively low binding energy (-52.8901 kcal/mol).

Keywords

Vanillyl alcohol, antibacterial activity, docking studies, glucosamine-6-phosphate synthase

Supporting Institution

None

Thanks

Kabir Yahuza, Department of Microbiology, Umaru Musa Yar’adua University, Katsina, Nigeria is gratefully acknowledged for the antibacterial assay.

References

• 1. Theuretzbacher U, Mouton JW. Update on antibacterial and antifungal drugs - Can we master the resistance crisis?. Current Opinion in Pharmacology. 2011;11: 429–32.
• 2. Walsh T, Toleman M. The emergence of pan-resistant gram-negative pathogens merits a rapid global political response. Journal of Antimicrobial Chemotherapy. 2012;67:1–3.
• 3. Awouafack MD, McGaw LJ, Gottfried S, Mbouangouere R, Tane P, Spiteller M, Eloff JN. Antimicrobial activity and cytotoxicity of the ethanol extract, fractions and eight compounds isolated from Eriosema robustum (Fabaceae). BMC Complementary and Alternative Medicine. 2013;13:1.
• 4. Srivastava J, Chandra H, Nautiyal AR, Kalra SJS: Antimicrobial resistance (AMR) and plant-derived antimicrobials (PDAms) as an alternative drug line to control infections. Biotechnology. 2013;4:451–60.
• 5. Neu HC. The crisis in antibiotic resistance. Science. 1992;257:1064–73.
• 6. Lowy F. Antimicrobial resistance: the example of Staphylococcus aureus. Journal of Clinical Investigation. 2003;111:1265–73.
• 7. Varshney V, Mishra NN, Shukla PK, Sahu DP. Synthesis of nitroimidazole derived oxazolidinones as antibacterial agents. European journal of medicinal chemistry. 2010;45(2):661-6.
• 8. Gupta K, Pandeya SN, Pathak AK, Gupta A. Synthesis and Antibacterial Activity of Ciprofloxacin Derivatives. Research Journal of Pharmacy and Technology. 2011;4(2):308-14.
• 9. Ye FQ, Ding YM, Chen L, Ye S, Chen ZX. Synthesis and antibacterial activity of ciprofloxacin derivatives. Acta pharmaceutica Sinica. 2005;40(2):132-5.
• 10. Mokaber-Esfahani M, Eshghi H, Akbarzadeh M, Gholizadeh M, Mirzaie Y, Hakimi M, Lari J. Synthesis and Antibacterial Evaluation of New Pyrimidyl N‐Ciprofloxacin Derivatives. ChemistrySelect. 2019;4(31):8930-3.
• 11. Rabbani MG, Islam MR, Ahmad M, Hossion AM. Synthesis of some NH-derivatives of ciprofloxacin as antibacterial and antifungal agents. Bangladesh Journal of Pharmacology. 2011;6(1):6-13.
• 12. Wang A, Xu Y. Synthesis and antibacterial activity of novel icariin derivatives. Die Pharmazie-An International Journal of Pharmaceutical Sciences. 2019;74(2):73-8.
• 13. Nitbani FO, Siswanta D, Sholikhah EN, Fitriastuti D. Synthesis and antibacterial activity 1-monolaurin. Oriental Journal of Chemistry. 2018;34(2):863.
• 14. Albert S, Horbach R, Deising HB, Siewert B, Csuk R. Synthesis and antimicrobial activity of (E) stilbene derivatives. Bioorganic & medicinal chemistry. 2011;19(17):5155-66.
• 15. Zhang HZ, He SC, Peng YJ, Zhang HJ, Gopala L, Tangadanchu VK, Gan LL, Zhou CH. Design, synthesis and antimicrobial evaluation of novel benzimidazole-incorporated sulfonamide analogues. European journal of medicinal chemistry. 2017;136:165-83.
• 16. Tiwari B, Pratapwar AS, Tapas AR, Butle SR, Vatkar BS. Synthesis and antimicrobial activity of some chalcone derivatives. International Journal of ChemTech Research. 2010;2(1):499-503.
• 17. Elenich OV, Lytvyn RZ, Blinder OV, Skripskaya OV, Lyavinets OS, Pitkovych Kh E, Obushak MD, Yagodinets PI. Synthesis and Antimicrobial Activity of 3-Phenyl-1-Methylquinolin-2-One Derivatives. Pharmaceutical Chemistry Journal. 2019; 52, 969–974.
• 18. Shingate BB, Hazra BG, Salunke DB, Pore VS, Shirazi F, Deshpande MV. Synthesis and antimicrobial activity of novel oxysterols from lanosterol. Tetrahedron. 2013;69(52):11155-63.
• 19. Paola V, Athina G, Kitka A, Matteo I, Franca Z, Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones. Bioorganic & Medicinal Chemistry. 2006;14(11),3859-3864.
• 20. Kumar KP, Vedavathi P, Subbaiah KV, Reddy DV. Design, synthesis, spectral characterization and bioactivity evaluation of new sulfonamide and carbamate derivatives of 5-Nitro-1H-indazole. Organic Communications. 2017;10(3):239-249.
• 21. Abdel-Rahman RM, Ali TE. Synthesis and biological evaluation of some new polyfluorinated 4-thiazolidinone and α-aminophosphonic acid derivatives. Monatshefte für Chemie-Chemical Monthly. 2013;144(8):1243-52.
• 22. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X, 1138.
• 23. NACDG Allergen: Benzyl alcohol. https://www.the-dermatologist.com/article/7191 (accessed May 4, 2020).
• 24. Barakat A., Al-majid A.M., Shahidul M.I., Warad I., Masand V.H, Yousuf S., Choudhary M.I. (2016). Molecular structure investigation and biological evaluation of Michael adducts derived from dimedone. Research on Chemical intermediates. 2016; 42(5): 4041-4053.
• 25. Borowski E. Novel approaches in the rational design of antifungal agents of low toxicity. Farmaco. 2000; 55:206-208.
• 26. Patel MM, Patel LJ. Synthesis, molecular docking and antibacterial evaluation of some novel fluoroquinolone derivatives as potent antibacterial agents. The Scientific World Journal. 2014.
• 27. Alam MS, Jebins S, Rahman MM, Bari Md L. Biological and quantitative SAR evaluation and docking studies of (E)-N-benzylidebenzo hydrazide analogues as potential antibacterial agents. EXCLI Journal. 2016; 15, 350-361.