Articles

Evaluation of anti-bacterial effects of some novel thiazole and imidazole derivatives against some pathogenic bacteria

Abstract

Background and Objectives: Bacterial resistance to antibiotics has motivated the researchers to evaluate the novel anti-bac- terial compounds such as some thiazole and imidazole derivatives. Thereby, in this work, we investigated the anti-bacterial effects of one new thiazole and two new imidazole derivatives on Bacillus cereus, Listeria monocytogenes, Escherichia coli, Salmonella typhimurium, Proteus mirabilis and Shigella dysenteriae.
Materials and Methods: The thiazole and imidazole derivatives were dissolved in DMSO. The disk diffusion method was utilized to measure the growth inhibition zone diameter values, and the broth micro-dilution method was applied to deter- mine the minimum inhibitory concentration (MIC) values.
Results: The synthesized imidazole derivatives lacked any inhibitory effect against the tested bacteria. On the other hand, although the synthesized thiazole derivative showed no inhibitory effect against Bacillus cereus, Salmonella typhimurium, and Escherichia coli, it inhibited the growth of Proteus mirabilis, Shigella dysenteriae, and Listeria monocytogenes with the MIC values of 1000, 125, and 1000 µg/ml, respectively, and the growth inhibition zone diameter values of 9.3 ± 0.1, 15.6 ± 0.2, and 8.1 ± 0.0 mm, respectively.
Conclusion: The anti-bacterial effect of the synthesized thiazole derivative on Shigella dysenteriae, Proteus mirabilis and Listeria monocytogenes was proven. However, its inhibition effect against Shigella dysenteriae was more than that against the others. Many in-vitro and in-vivo experiments are required to evaluate the effects of this compound on the bacteria and the human body.

Giesker K, Hensel M. Bacterial Vaccines. Ref Mod Bio Sci 2014;doi:10.1016/B978-0-12-801238-3.00141-0.

Chandra Sahu M, Nath Padhy R. In vitro antibacterial potency of Butea monosperma Lam. against 12 clini- cally isolated multidrug resistant bacteria. Asian Pac J Trop Dis 2013;3: 217-226.

Soares M, Brito A, Laranjo M, Paixao J, Botel- ho M, PinhoeMelo T. Chiral 6,7-bis(hydroxymeth- yl)-1H,3H-pyrrolo[1,2-c]thiazoles with anti-breast cancer properties. Eur J Med Chem 2013;60: 254-262.

Helul MHM, Salem MA, El-Gaby MSA, Aljahdali M. Synthesis and biological evaluation of some nov- el thiazole compounds as potential anti-inflammatory agents. Eur J Med Chem 2013;65: 517-526.

Venugopla KN, Krishnappa M, Nayak SK, Subruh- many BK, Vaderapura, JP, Chalannavar RK, et al. Synthesis and antimosquito properties of 2,6-substi- tuted benzo[d] thiazole and 2,4-substituted benzo[d] thiazole analogues against Anopheles arabiensis. Eur J Med Chem 2013;65: 295–303.

Chementi F, Bizzarri B, Bolasco A, Secci D, Chimenti P, Granese A, et al. Synthesis and biological evaluation of novel 2,4-disubstituted-1,3-thiazoles anti Candida spp agents. Eur J Med Chem 2011;46: 378-382.

Aggarwal R, Kumar S, Kaushik P, Kaushik D, Gupta G. Synthesis and pharmacological evaluation of some novel 2-(5-hydroxy-5-trifluoromethyl-4,5-di- hydropyrazol-1-yl)-4-(coumarin-3-yl) thiazoles. Eur J Med Chem 2013;62: 508-514.

Wittine K, Stipkovic-Babic M, Makuc D, Plavec J, Kraljevic-Pavelic S, Sedic M, et al. Novel 1,2,4-tri- azole and imidazole derivatives of L-ascorbic and imi- no-ascorbic acid: Synthesis, anti-HCV and antitumor activity evaluations. Bioorg Med Chem 2012;20: 3675-3685.

Brahmayya M, Venkateswararao B, Krishnarao D, Durgarao S, Viplava Prasad U, Damodharam T, et al. Synthesis and fungicidal activity of novel 5-aryl-4- methyl-3yl (imidazolidin-1yl methyl, 2-ylidene nitro imine) isoxazoles. J Pharm Res 2013;7: 516-5 1 9.

Jean-Michel HR, Sabourin C, Alvarez N, Piessard SR, Le Baut G, Le Pape P. Synthesis and antileishmanil activity of new imidazolidin-2-one derivatives. Eur J Med Chem 2003;38: 711-718.

Salhi L, Bouzroura-Aichouche S, Benmalek Y, Ben- malek B, Poulain-Martini S, Cacciuttolo B, et al. An efficient conversion of maleimide derivatives to 2-thi- oxo imidazolidinones. Org Commun 2013;6: 87-94.

Bakavoli, M, Beyzaei H, Rahimizadeh, M, Eshghi H. Regioselective synthesis of 2[(E)-(benzo[d]thiaz- ol2 (3H)ylidene)(cyano)methyl] thiazoles. Heterocycl Commun 2011;17: 151-154.

Beyzaei H, Aryan R, Gomroki M. Synthesis of novel heterocyclic 2-(2-ylidene) malononitrile derivatives. Org Chem Indian J 2014; ID: OCAIJ_2525.

Khalil A, Berghot M, Gouda M. Synthesis and anti- bacterial activity of some new thiazole and thiophene derivatives. Eur J MedChem 2009;44: 4434-4440.

Jones RN, Wilson ML, Weinstein MP, Stilwell MG, Mendes RE. Contemporary potencies of minocycline and tetracycline HCL tested against Gram-positive pathogens: SENTRY Program results using CLSI and EUCAST breakpoint criteria. Diagn Microbiol Infect Dis 2013; 75: 402–405.

Shahid HA, Jahangir S, Yousuf S, Hanif M, Sher- wan SK. Synthesis, crystal structure, structural char- acterization and in vitro antimicrobial activities of 1-methyl-4-nitro-1H-imidazole. Arab J Chem 2014;doi:10.1016/j.arabjc.2014.11.001.

Cheng K, Xue JY, Zhu HL. Design, synthesis and an- tibacterial activity studies o thiazole derivatives as po- tent eckAS inhibitors. Bioorg Med Chem Lett 2013;23:4235-4238.

Brvar M, Perdih A, Oblak M, Masic LP, Solmajer T. In silico discovery of 2-amino-4-(2,4-dihydroxyphenyl) thiazoles as novel inhibitors of DNA gyrase B. Bioorg Med ChemLett 2010; 20: 958–962.

Maddila S, Gorle S, Seshadri N, Lavanya P, Jonnal- agadda SB. Synthesis, antibacterial and antifungal ac- tivity of novel benzothiazole pyrimidine derivatives. Arab J Chem 2013; doi: 10.1016.04.003.

Patel R, Patel PK, Kumari P, Rajani DP, Chikhalia KH.Synthesis of benzimidazolyl-1,3,4-oxadiazol-2ylthio- N-phenyl (benzothiazolyl) acetamides as antibacteri- al, antifungal and antituberculosis agents. Eur J Med Chem 2012;53: 41-51.

Gilani SJ, Nagarajan K, Dixit SP, Taleuzzaman M, Khan SA. Benzothiazole incorporated thiazoli- din-4-ones and azetidin-2-ones derivatives: Synthesis and in vitro antimicrobial evaluation. Arab J Chem 2012;doi: 10.1016/j.arabjc.04.004.

Alizadeh R, Yousuf I, Afzal M, Srivastav S, Srikrish-na S, Arjmand F. Enantiomericfluoro-substituted ben- zothiazole Schiff base-valine Cu(II)/Zn(II) complex- es as chemotherapeutic agents: DNA bindingprofile, cleavage activity, MTT assay and cell imaging studies. J Photochem Photobiol B2015; 143: 61–73.

Jagani CL, Sojitra NA, Vanparia SF, Patel TS, Dix- it RB, Dixit BC. Microwave promoted synthesis and antimicrobial activity of 3-thiazole substituted 2-sty- ryl-4(3H)-quinazolinone derivatives. J Saudi Chem Soc 2012;16: 363–369.

Bharti S, Nath G, Tilak R, Singh S. Synthesis, an- ti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring. Eur J MedChem 2010;45: 651–660.

Juspin T, Laget M, Terme T, Azas N, Vanelle P.TDAE-assisted synthesis of new imidazo[2,1-b]thi- azole derivatives as anti-infectious agents. Eur J Med- Chem 2010;45: 840–845.

Files
IssueVol 7 No 5 (2015) QRcode
SectionArticles
Keywords
Antibacterial effects Thiazole Imidazole

Rights and permissions
Creative Commons License This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
How to Cite
1.
Ghasemi B, Sanjarani G, Sanjarani Z, Majidiani H. Evaluation of anti-bacterial effects of some novel thiazole and imidazole derivatives against some pathogenic bacteria. Iran J Microbiol. 2015;7(5):281-286.