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Abstract
Purpose : To study the structure-activity relationships of synthetic multifunctional sulfides through evaluation of lipoxygenase and anti-bacterial activities. Methods : S-substituted derivatives of the parent compound 5-(1-(4- chlorophenylsulfonyl) piperidin-3- yl)-1, 3, 4-oxadiazole-2-thiol were synthesized through reaction with different saturated and unsaturated alkyl halides in DMF medium, with NaH catalyst. Spectral characterization of each derivative was carried out with respect to IR, 1H - NMR, 13C - NMR and EI - MS. The lipoxygenase inhibitory and antibacterial activities of the derivatives were determined using standard procedures . Results : Compound 5e exhibited higher lipoxygenase inhibitory potential than the standard (Baicalein®), with % inhibition of 94.71 ± 0.45 and IC50 of 20.72 ± 0.34 μmoles/L. Compound 5b showed significant antibacterial potential against all the bacterial strains with % inhibition ranging from 62.04 ± 2.78, 69.49 ± 0.41, 63.38 ± 1.97 and 59.70 ± 3.70 to 78.32 ± 0.41, while MIC ranged from 8.18 ± 2.00, 10.60 ± 1.83, 10.84 ± 3.00, 9.81 ± 1.86 and 11.73 ± 5.00 μmoles/L for S. typhi, E. coli, P. aeruginosa, B. subtilis and S. aureus, respectively. Compounds 5d, 5e and 5g showed good antibacterial activity against S. typhi and B. subtilis bacterial strains. Conclusion : The results suggest that compound 5e bearing n-pentyl group is a potent lipoxygenase inhibitor, while compound 5b with n-propyl substitution is a strong antibacterial agent. In addition, compounds 5d, 5e and 5g bearing n-butyl, n-pentyl and n-octyl groups, respectively, are good antibacterial agents against S. typhi and B. subtilis. Keywords : Sulfides, Antibacterial activity, Lipoxygenase activity, Spectral analysis
Highlights
Millions of people suffer from bacterial infectious diseases which are among the leading causes of morbidity and mortality worldwide [1,2]
The treatment and management of bacterial infectious diseases are hampered by numerous factors, including the emergence of multi-drug resistant strains of bacteria [3]
The IR spectra of Compound 5b revealed the presence of C=N at 1589 cm-1, aromatic C=C double bond was confirmed by bands at 1537 cm-1 and presence of sulfonyl group at about 1324 cm-1. 1H-NMR recorded at 400 MHz using CDCl3 as solvent gave characteristic two doublets at 7.70 and 7.50 ppm for 4-chlorophenyl sulfonyl group while signals for piperidine ring have a broad range of chemical shift value varying for each axial and equatorial proton
Summary
Millions of people suffer from bacterial infectious diseases which are among the leading causes of morbidity and mortality worldwide [1,2]. At the end of the reaction, the flask contents were neutralized and precipitates were filtered, washed with distilled water and recrystallized in ethanol. Cold distilled water was introduced to the reaction mixture and the precipitates were filtered, washed with water and recrystallized from ethanol. The reaction contents were dissolved in distilled water and acidified to obtain the oxadiazole precipitates. Synthesis of S-substituted derivatives of 5-{1[(4-chlorophenyl) sulfonyl]-3-piperidinyl}-1, 3, 4-oxadiazol-2-yl sulfide. Different saturated/unsaturated alkyl halides (1 mmol) were added separately to the reaction mixture in the round bottom flask and the mixture was stirred for 4 h. A total volume of 200 μL assay mixture contained 150 μL sodium phosphate buffer (100 mM, pH 8.0), 10 μL test compound and 15 μL purified lipoxygenase (Sigma, USA). 5-{1-[(4-Chlorophenyl) sulfonyl]-3-piperidinyl} -1, 3, 4-oxadiazol-2-yl ethyl sulfide (Compound 5a). 5-{1-[(4-Chlorophenyl) sulfonyl]-3-piperidinyl} -1, 3, 4-oxadiazol-2-yl propyl sulfide (Compound 5b)
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