One-step Synthesis of Ethyl and Methyl Derivatives of Ylidene-Acetate Bonded at Position 5 of Ring 1,3-Thiazole and Evaluation of Their Antibacterial Activities

Document Type : Original article

Authors

1 PhD Student of Microbiology, Department of Biology, Central Tehran Branch, Islamic Azad University, Tehran, Iran

2 MSc Student of Microbiology, Department of Microbiology, Tehran North Branch of Islamic Azad University, Tehran, Iran.

Abstract

Introduction: The emergence of drug resistance in bacteria is a serious threat to human health; therefore, new thiazole derivatives can be good alternatives for common drugs. In this regard, the aim of this study was the one-step synthesis of ethyl and methyl derivatives of ylidene-acetate bonded at position 5 of ring 1,3-thiazole and evaluation of their antibacterial activities. 
Materials and Methods: From the single-step reaction between thiourea and acetylene decarboxylase derivatives in acetone solvent, the new thiazole structures were derived based on ethyl and methyl, and they were investigated and confirmed by spectroscopic methods, including infrared, carbon nuclear magnetic resonance, and hydrogen proton nuclear magnetic resonance. The antibacterial properties of this isomer were assessed applying minimal inhibitory concentration, minimum bactericidal concentration, and disc diffusion methods. These properties were tested with three repetitions on Staphylococcus aureus, Staphylococcus epidermidis, and Bacillus cereus at a concentration of 1 mg/ml.
Results: The results of the present study showed that the strongest inhibitory effect (R2=250 mg/ml) and highest diameterof the inhibitory zone (R2=34±1/55 mm) of the derivatives used in this experiment were related to Staphylococcus aureus as the same effect of conventional antibacterial drugs.
Conclusion: The results of this study indicated that the new single-step 1,3-thiazole derivatives have very good antibacterial activities against gram-positive bacteria.

Keywords

References

  1. Lee S, Eom MS, Han MS. Multi-screening of β-lactam antibiotics for β-lactamase resistance by means of a paper-based analytical device with a 4-(2-pyridylazo) resorcinol (PAR)–Hg 2+ complex. Analyt Methods. 2019; 11(13):1729-34.
  2. Tian J, Xiao C, Huang B, Jiang X, Cao H, Liu F, et al. Combating multidrug resistance through an NIR-Triggered cyanine-containing amphiphilic block copolymer. ACS Appl Bio Mater. 2019; 2(5):1862-74.
  3. Chatzopoulou M, Reynolds L. The role of antimicrobial restrictions in bacterial resistance control: a systematic literature review. J Hosp Infect. 2020; 104(2):125-36.
  4. Rather IA, Kim BC, Bajpai VK, Park YH. Self-medication and antibiotic resistance: Crisis, current challenges, and prevention. Saudi J Biol Sci. 2017; 24(4):808-12.
  5. Frija LM, Pombeiro AJ, Kopylovich MN. Coordination chemistry of thiazoles, isothiazoles and thiadiazoles. Coordinat Chem Rev. 2016; 308:32-55.
  6. Paerl RW, Bouget FY, Lozano JC, Vergé V, Schatt P, Allen EE, et al. Use of plankton-derived vitamin B1 precursors, especially thiazole-related precursor, by key marine picoeukaryotic phytoplankton. ISME J. 2017; 11(3):753-95.
  7. Qureshi A, Pradhan A. Short review on thiazole derivative. J Drug Deliv Ther. 2019; 9(4-A):842-7.
  8. Jain N, Singh B. An overview of biological and synthetic aspects of thiazole derivatives in heterocyclic chemistry. World J Res Rev. 2016; 3(5):52-7.
  9. Piechowicz KA, Truong EC, Javed KM, Chaney RR, Wu JY, Phuan PW, et al. Synthesis and evaluation of 5, 6-disubstituted thiopyrimidine aryl aminothiazoles as inhibitors of the calcium-activated chloride channel TMEM16A/Ano1. J Enzyme Inhib Med Chem. 2016; 31(6):1362-8.
  10. Krimm I, Kufareva I, Ashraf A, Kamal M, Seetoh WG, Abell C, et al. 2‑Aminothiazole derivatives as selective allosteric modulators of the protein kinase CK2. 1. identification of an allosteric binding site. J Med Chem. 2019; 62:1803-16.
  11. Tamarkin D, Friedman D, Eini M, Besonov
    A, Danziger J, Schuz D, et al. Oleaginous pharmaceutical and cosmetic foam. U S Patent Appl. 2007; 11(653);205.
  12. Sokhey SS, Wagle PM. A note on the use of sulphonamides in the treatment of plague in the field. Ind Med Gaz. 1946; 81(9):343-6.
  13. Bharti SK, Nath G, Tilak R, Singh SK. Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2, 4-disubstituted thiazole ring. Eur J Med Chem. 2010; 45(2):651-60.
  14. Liang X, Yu X, Pan X, Wu J, Duan Y, Wang J, et al. A thiadiazole reduces the virulence of Xanthomonas oryzae pv. oryzae by inhibiting the histidine utilization pathway and quorum sensing. Mole Plant Pathol. 2018; 19(1):116-28.
  15. Gull Y, Rasool N, Noreen M, Altaf A, Musharraf SG, Zubair M, et al. Synthesis of N-(6-Arylbenzo [d] thiazole-2-acetamide derivatives and their biological activities: an experimental and computational approach. Molecules. 2016; 21(3):266.
  16. Owuama CI. Determination of minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) using a novel dilution tube method. Afr J Microbiol Res. 2017; 11(23):977-80. 
  17. Lhermie G, Gröhn YT, Raboisson D. Addressing antimicrobial resistance: an overview of priority actions to prevent suboptimal antimicrobial use in food-animal production. Front Microbiol. 2017; 7:2114.
  18. Hou L, Shi Y, Zhai P, Le G. Antibacterial activity and in vitro anti-tumor activity of the extract of the larvae of the housefly (Musca domestica). J Ethnopharmacol. 2007; 111(2):227-31.
  19. Amoo S, Ndhlala AR, Finnie JF, Van Staden J. Antibacterial, antifungal and anti-inflammatory properties of Burchellia bubaline. South Afr J Botany. 2009; 75(4):60-3.
  20. Rai NP, Narayanaswamy VK, Shashikanth S, Arunachalam PN. Synthesis characterization
    and antibacterial activity of 2-[1-(5-chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl]-5. substitutedphenyl)-[1,3,4] oxadiasoles. Eur J Med Chem. 2009; 44(3):4522-7.
  21. Karegoudar P, Karthikeyan MS, Prasad DJ, Mahalinga M, Holla BS, Kumari NS. Synthesis of some novel 2,4-disubstituted thiazoles as possible antimicrobial agents. Eur J Med Chem. 2008; 43(2):261-7.
  22. Lv PC, Wang KR, Yang Y, Mao WJ, Chen J, Xiong J, et al. Design, synthesis and biological evaluation of novel thiazole derivatives as potent FabH inhibitors. Bioorg Med Chem Let. 2009; 19(23):6750-4.
  23. Zablotskaya A, Segal I, Geronikaki A, Eremkina
    T, Belyakov S, Petrova M, et al. Synthesis, physicochemical characterization, cytotoxicity, antimicrobial, anti-inflammatory and psychotropic activity of new N-[1, 3-(benzo) thiazol-2-yl]-u-[3, 4-dihydroisoquinolin-2(1H)-yl] Alkanamides. Eur J Med Chem. 2013; 70:846-56.
  24. Maddila S, Gorle S, Seshadri N, Lavanya P, Jonnalagadda SB. Synthesis, antibacterial and antifungal activity of novel benzothiazole pyrimidine derivatives. Arabian J Chem. 2016; 9(5):981-7.
  25. Behzad G, Hamid B, Mohsen N. The antibacterial effects of the new derivatives of Thiazole, Imidazole and Tetrahydropyridine against Proteus vulgaris: an in vitro study. Pars J Med Sci. 2016; 13(4):47-55.
  26. Bondock S, Khalifa W, Fadda AA. Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3, 4-dihydronaphthalene-2-carboxaldehyde. Eur J Med Chem. 2007; 42(7):948-54.
Navid No
Volume 23, Issue 73
June 2020
Pages 66-77

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