The new Schiff bases of 2-alkylthio-5-(4-aminophenyl)-1,3,4-oxadiazoles and their antimicrobial activity
- 14 Downloads
By the reaction of 5-(4-aminophenyl)-1,3,4-oxadiazolin-2-thione with alkyl halides 2-alkylthio-5-(4-aminophenyl)-1,3,4-oxadiazoles, 2–4 were obtained. By the reaction of compounds 2–4 with aromatic aldehydes, new Schiff bases 5a–d and 6a–d were synthesized. The structures of synthesized compounds are confirmed by the IR, UV, 1H NMR for all compounds, 13C NMR for compounds 3, 4, 5a–5d, 6a, 6d and X-ray for compound 3. All substances were tested in vitro for their antibacterial and antifungal activity. The results showed that Compound 2 exhibited remarkable activity against Candida albicans. Compounds 5а–d were found to exhibit a weak selective activity against Gram-positive bacteria of Bacillus subtilis and compounds 6а–d against Gram-negative bacteria of Escherichia coli.
Keywords5-(4-Aminophenyl)-1,3,4-oxadiazol-2-thione Aromatic aldehyde Amino group NMR spectra X-ray analysis Antimicrobial activity
Authors are thankful to the Academy of Sciences of the Republic of Uzbekistan for supporting this study (Grant VA-FA-F7-006 and FA-F6-T198).
Compliance with ethical standards
Conflict of interest
There is no conflict of interest associated with the authors of this paper.
- 2.R. Kharb, R. Kaur, A.K. Sharma, Eur. J. Biomed. Pharm. Sci. 1, 401 (2014)Google Scholar
- 3.R. Sharma, N. Kumar, R. Yaday, Res. Rev. J. Chem. 4, 1 (2015)Google Scholar
- 4.P. Dholaria, K. Parikh, J. Deepkumar, Int. J. ChemTech Appl. 4, 1 (2015)Google Scholar
- 5.S. Rasool, M.A. Aziz-ur-Rehman, S.Z. Abbasi, S.A. Siddiqui, A. Shah, BJPS 52, 471 (2016)Google Scholar
- 6.A. Siddiqa, et al., Pak. J. Pharm. Sci. 29, 27 (2016)Google Scholar
- 7.D.S. Ismailova, A.A. Ziyaev, B.Z. Elmuradov, T.T. Toshmurodov, Kh.M. Bobakulov, R.P. Zakirova, J. Basic Appl. Res. 2, 476 (2016)Google Scholar
- 8.A.A. Ziyaev, I.F. Tozhiev, S.A. Sasmakov, S.S. Azimova, B.Z. Elmuradov, D.S. Ismailova, Pharm. Chem. J. 4, 29 (2017)Google Scholar
- 11.Clinical and Laboratory Standards Institute (CLSI) Performance Standards for Antimicrobial Disk Diffusion Susceptibility Tests, approved standard, 19th edn. (CLSI Document M100-S19, Wayne, 2009)Google Scholar
- 12.T. Lindl, J. Bauer, Zell und Gewebekultur (Gustav-Fischer-Verlag Jena, Berlin, 1989)Google Scholar
- 13.DIN Taschenbuch 222, Medizinische Mikrobiologie und Immunologie (Beuth-Verlag, Berlin, 2004)Google Scholar
- 14.CrysAlisPro, Oxford Diffraction. (Oxford Diffraction Ltd, Abingdon, 2007)Google Scholar
- 17.S. Vijayaraghavan, R.R. Somani, P.Y. Shirodkar, V.J. Kadam, Int. J. PharmTech. Res. 1, 811 (2009)Google Scholar