Article Sidebar
Published:
Sep 7, 2017Keywords:
Article Details
Submission of a manuscript to this journal is a representation that the manuscript has not been published previously and is not under consideration for publication elsewhere.
All authors named in each manuscript would be required to sign a form (to be supplied by the Editor) so that they may retain their copyright in the article but to assign to us (the Publishers) and its licensees in perpetuity, in all forms, formats and media (whether known or created in the future) to (i) publish, reproduce, distribute, display and store the contribution, (ii) translate the contribution into other languages, create adaptations, reprints, include within collections and create summaries, extracts and/or abstracts of the contribution, (iii) create any other derivative works(s) based on the contribution, (iv) to exploit all subsidiary rights in the contribution, (v) the inclusion of electronic links from the contribution to third party material where-ever it may be located, and (vi) license any thrid party to do any or all of the above.
Main Article Content
Antimicrobial, hemolytic and thrombolytic activities of some new N-substituted-2-({5-[(1E,3E)F-4-(1,3-benzodioxol- 5-yl)-1,3-butadienyl]-1,3,4-oxadiazol-2-yl}sulfanyl) propanamides
Abstract
Purpose: To synthesize and evaluate the bioactivity of some N-substituted-2-({5-[(1E,3E)-4-(1,3- benzodioxol-5-yl)-1,3-butadienyl]-1,3,4-oxadiazol-2-yl}sulfanyl)propanamides (9a-o) of the alkaloid piperine (1) extracted from P. nigrum (black pepper).
Methods: Extract 1 was subjected to basic hydrolysis to obtain piperic acid (2). The heterocyclic 1,3,4- oxadiazole ring was synthesized from 2 through the formation of an ester and carbohydrazide. A series of electrophiles, 8a-o, were synthesized in the presence of 10 % Na2CO3. The final compounds, 9a-o, were synthesized by stirring 5-[(1E,3E)-4-(1,3-benzodioxol-5-yl)-1,3-butadienyl]-1,3,4-oxadiazol-2-thiol (5) and 8a-o in LiH/DMF. Spectral analysis was performed using infrared (FTIR), proton nuclear magnetic resonance (1H-NMR) and electron impact mass spectrometry (EI-MS) to determine the structures of 9a-o. Antimicrobial activity was evaluated as zone of inhibition by disc diffusion method. Hemolytic and thrombolytic activities were determined by measuring absorbance before and after incubation of blood cells with test compound.
Results: Compound 9d strongly inhibited Bacillus subtilis and Escherichia coli with zone of inhibition values of 16 mm for each. The reference drug, rifampicin, showed zone of inhibition of 21 and 23 mm against B. subtilis and E. coli, respectively. Compound 9a strongly inhibited Aspergillus niger with a zone of inhibition of 18 mm compared to the reference drug, fluconazole, with a zone of inhibition of 19mm.
Conclusion: The newly synthesized compounds are more active antimicrobial agents than piperine. Compounds 9a and 9d are the most active.
Keywords: Piper nigrum, Piperine, Propanamide, Hemolytic, Thrombolytic, Black pepper
