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Tropical Journal of Pharmaceutical Research
Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, Nigeria
ISSN: 1596-5996
EISSN: 1596-5996
Vol. 14, No. 6, 2015, pp. 1081-1088
Bioline Code: pr15142
Full paper language: English
Document type: Research Article
Document available free of charge

Tropical Journal of Pharmaceutical Research, Vol. 14, No. 6, 2015, pp. 1081-1088

 en Synthesis of N'-Substituted-2-(5-(4-Chlorophenyl) - 1,3,4-oxadiazol-2-ylthio)acetohydrazide Derivatives as Suitable Antibacterial Agents
Rasool, S.; Aziz-ur-Rehman; Abbasi, M.A.; Gul, S.; Akhtar, M.N.; Ahmad, I. & Afzal, S.

Abstract

Purpose: To evaluate antibacterial activity of a series of molecules bearing 1,3,4-oxadiazole and azomethine moieties.
Methods: The 4-chlorobenzoic acid (1) was precursor to N'-substituted-2- (5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetohydrazide, 8a-p, through a multistep synthesis of corresponding ester, 2, hydrazide, 3 and 1,3,4-oxadiazole, 4. The molecule, 4, was subjected to electrophilic substitution by ethyl-2-bromoacetate to yield 5 which was stepped to 2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetohydrazide (6). The target molecules, 8a-p, were synthesized by nucleophilic addition of 6 to arylaldehydes, 7a-p. The proposed structures of all the synthesized molecules were elucidated by Infra Red (IR), Proton Nuclear Magnetic Resonance (1H-NMR) and Electron Impact Mass Spectrometry (EI-MS) spectral data. Antibacterial activity was evaluated by the principle that microbial growth is in a log phase of growth and so results in increased absorbance of broth medium which is observed.
Results: The molecule, 8b, was active against S. aureus check for this species in other resources and 8c against S. typhi check for this species in other resources only. The molecule, 8p, was the most active against S. typhi with minimum inhibitory concentration (MIC) value of 10.04 ± 1.25 μM while 8e was active against E. coli with MIC of 9.45 ± 1.00 μM, both relative to the reference standard, ciprofloxacin, which displayed MIC of 9.13 ± 2.00 and 8.90 ± 1.65 μM, respectively.
Conclusion: Most of the synthesized molecules exhibit 50 % antibacterial activity relative to the reference. Molecules 8b and 8c are the least active compounds

Keywords
1,3,4-Oxadiazole; 4-Chlorobenzoic acid; Antibacterial activity; Azomethine

 
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