Synthesis and Antimicrobial Activity of Newly Synthesized 2-((5-(4-(5(6)fluoro-1H-benzo[d]imidazol-2-yl)phenyl)-1,3,4-oxadiazol-2-yl)thio)-Derivatives †
by
and
Abdullah Burak Karaduman
1,*, 
Ulviye Acar Çevik
2,3,
Derya Osmaniye
2,3,
Yusuf Özkay
2,3 and
Sinem Ilgın
1,3 1
Department of Pharmaceutical Toxicology, Faculty of Pharmacy, Anadolu University, 26470 Eskişehir, Turkey
2
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, 26470 Eskişehir,Turkey
3
Doping and Narcotic Compounds Analysis Laboratory, Faculty of Pharmacy, Anadolu University,26470 Eskişehir, Turkey
*
Author to whom correspondence should be addressed.
†
Presented at the 1st Molecules Medicinal Chemistry Symposium, Barcelona, Spain, 8 September 2017.
Proceedings 2017, 1(6), 639; https://doi.org/10.3390/proceedings1060639
Published: 18 October 2017
(This article belongs to the Proceedings of Proceedings of the 1st Molecules Medicinal Chemistry Symposium, Barcelona, Spain)
Benzimidazole derivatives have a great deal of interest in terms of antimicrobial therapy. Thus, in the present study, new benzimidazole derivatives were obtained to perform antimicrobial activity. The 4-(5(6)fluoro-1H-benzo[d]imidazol-2-yl)benzoate (1) obtained by 4-fluoro-o-phenylenediamine and methyl 4-formylbenzoate, was reacted with hydrazine hydrate to afford 4-(5(6)fluoro-1H-benzo[d]imidazol-2-yl)benzohydrazide (2). The reaction of compound 2 with CS2 in the presence of NaOH gave 5-(4-(5(6)fluoro-1H-benzo[d]imidazol-2-yl)phenyl)-1,3,4-oxadiazole-2-thiol (3), which was reacted with substituted bromide derivatives to obtain final compounds.
The structures of all the compounds were established on the basis of elemental and spectral analysis. Antimicrobial activities of the compounds against resistant human pathogenic microorganisms were evaluated according to the CLSI methods [1,2]. Final products were tested for their in vitro growth inhibitory activity against human pathogenic Escherichia coli (ATCC 35218), Escherichia coli (ATCC 25922), Staphylococcus aureus (ATCC 25923), Pseudomona aeuroginosa (ATCC 27853), and yeast as Candida albicans (ATCC 90028), Candida glabrata (ATCC 90030), Candida krusei (ATCC 6258), and Candida parapsilosis (ATCC 22019). Chloramphenicol and ketoconazole were used as control drugs. The compound 4I containing 3,4-dihydroxyphenyl moiety in its structure exhibited the highest activity against Candida krusei ATCC 6258, Candida glabrata ATCC 90030, and Candida parapsilosis ATCC 22019. Furthermore, the cytotoxic effects of the synthesized compounds were determined by in vitro activity tests.
Author Contributions
Y.Ö. conceived and designed the experiments; D.O. and U.A.Ç. performed the synthesis; A.B.K. and S.I. performed activity tests and toxicity tests; A.B.K., Y.Ö., S.I, U.A.Ç. and D.O. wrote the paper. All authors have read and agreed to the published version of the manuscript.
Acknowledgments
This study was financially supported by Anadolu University Scientific Projects Fund, Project No: 1705S312.
Conflicts of Interest
The authors declare no conflict of interest.
References
- Clinical and Laboratory Standarts Institue (CLSI). Methods for Dilution Antimicrobial Sceptibilitytests for Bacteria that Grow Aerobically, CLSI M7-A7; Clinical and Laboratory Standards Institue: Wayne, PA, USA, 2006. [Google Scholar]
- Clinical and Laboratory Standards Institute (CLSI). Reference Method for Broth Dilution Antifungal SusceptibilityTesting of Yeast, Approved Standard, CLSI 27-A3, 3rd ed.; Clinical and Laboratory Standards Institue: Wayne, PA, USA, 2008. [Google Scholar]
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MDPI and ACS Style
Karaduman, A.B.; Çevik, U.A.; Osmaniye, D.; Özkay, Y.; Ilgın, S. Synthesis and Antimicrobial Activity of Newly Synthesized 2-((5-(4-(5(6)fluoro-1H-benzo[d]imidazol-2-yl)phenyl)-1,3,4-oxadiazol-2-yl)thio)-Derivatives. Proceedings 2017, 1, 639. https://doi.org/10.3390/proceedings1060639
AMA Style
Karaduman AB, Çevik UA, Osmaniye D, Özkay Y, Ilgın S. Synthesis and Antimicrobial Activity of Newly Synthesized 2-((5-(4-(5(6)fluoro-1H-benzo[d]imidazol-2-yl)phenyl)-1,3,4-oxadiazol-2-yl)thio)-Derivatives. Proceedings. 2017; 1(6):639. https://doi.org/10.3390/proceedings1060639
Chicago/Turabian StyleKaraduman, Abdullah Burak, Ulviye Acar Çevik, Derya Osmaniye, Yusuf Özkay, and Sinem Ilgın. 2017. "Synthesis and Antimicrobial Activity of Newly Synthesized 2-((5-(4-(5(6)fluoro-1H-benzo[d]imidazol-2-yl)phenyl)-1,3,4-oxadiazol-2-yl)thio)-Derivatives" Proceedings 1, no. 6: 639. https://doi.org/10.3390/proceedings1060639
