Abstract:This research was focused on in silico characterization and in vitro biological testing of the series of the compounds carrying a N-arylpiperazine moiety. The in silico investigation was based on the prediction of electronic, steric and lipohydrophilic features. The molecules were screened against Mycobacterium avium subsp.paratuberculosis CIT03, M. smegmatis ATCC 700084, M. kansasii DSM 44162, M. marinum CAMP 5644, Staphylococcus aureus ATCC 29213, methicillin-resistant S. aureus 63718, Escherichia coli ATCC 25922, Enterococcus faecalis ATCC 29212, Candida albicans CCM 8261, C. parapsilosis CCM 8260 and C. krusei CCM 8271, respectively, by standardized microdilution methods. The eventual antiproliferative (cytotoxic) impact of those compounds was examined on a human monocytic leukemia THP-1 cell line, as a part of the biological study. Promising potential against M. kansasii was found for 1-[3-(3-ethoxyphenylcarbamoyl)oxy-2-hydroxypropyl]-4-(3-trifluoromethylphenyl)piperazin-1-ium chloride (MIC = 31.75 µM), which was comparable to the activity of isoniazid (INH; MIC = 29.17 µM). Moreover, 1-{2-hydroxy-3-(3-methoxyphenylcarbamoyl)oxy)propyl}-4-(4-fluorophenyl)piperazin--1-ium chloride was even more effective (MIC = 17.62 µM) against given mycobacterium. Among the tested N-arylpiperazines, 1-{2-hydroxy-3-(4-methoxyphenylcarbamoyl)oxy)propyl}-4-(3-trifluoromethylphenyl)piperazin-1-ium chloride was the most efficient against M. marinum (MIC = 65.32 µM). One of the common features of all investigated substances was their insignificant antiproliferative (i.e., non-cytotoxic) effect. The study discussed structure-antimicrobial activity relationships considering electronic, steric and lipophilic properties.

not availableDhaka Univ. J. Pharm. Sci. 15(2): 235-239, 2016 (December)

In an effort to comprehensively characterize an antioxidant profile of 2-alkoxyphenylcarbamic acid-based compounds containing a 4´-(substituted phenyl)piperazin-1´-yl fragment, they were in vitro screened in the 2,2´-azino-bis(3-ethylbenzothiazoline-6--sulfonic acid) derived radical cation (ABTS •+ ) and ferric reducing antioxidant power (FRAP) assay using the UV/VIS spectrophotometry. The ABTS•+ scavenging (reducing) potential of 1-[3-(2-methoxyphenylcarbamoyl)oxy-2-hydroxypropyl]-4-(4--fluorophenyl)piperazin-1-ium chloride was found to be the most promising and it was comparable to the efficiency of the carvedilol reference drug. Moreover, that 4´-fluoro group-containing compound was regarded as more active than the atenolol standard. When testing the molecules´ power to reduce the ferric 2,4,6-tris (2-pyridyl)-s-triazine complex [Fe(III)(TPTZ) 2 ] 3+ , the most prospective was 1-[3-(2-ethoxyphenylcarbamoyl)oxy-2--hydroxypropyl]-4-(4-fluorophenyl)piperazin-1-ium chloride. On the other hand, its Fe 3+ reducing power was lower compared to both standards carvedilol and atenolol. The study discussed structure-antioxidant properties relationships considering electronic, steric and lipophilic features.

not available DOI: http://dx.doi.org/10.3329/dujps.v13i2.21903 Dhaka Univ. J. Pharm. Sci. 13(2): 215-219, 2014 (December)

No abstract