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Molecules 2014, 19(6), 7152-7168; doi:10.3390/molecules19067152

Diethyl 2-(Phenylcarbamoyl)phenyl Phosphorothioates: Synthesis, Antimycobacterial Activity and Cholinesterase Inhibition

1
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
2
Department of Biological and Biochemical Sciences, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic
3
Laboratory for Mycobacterial Diagnostics and Tuberculosis, Regional Institute of Public Health in Ostrava, Partyzánské náměstí 7, 702 00 Ostrava, Czech Republic
*
Author to whom correspondence should be addressed.
Received: 29 April 2014 / Revised: 26 May 2014 / Accepted: 27 May 2014 / Published: 30 May 2014
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A new series of 27 diethyl 2-(phenylcarbamoyl)phenyl phosphorothioates (thiophosphates) was synthesized, characterized by NMR, IR and CHN analyses and evaluated against Mycobacterium tuberculosis H37Rv, Mycobacterium avium and two strains of Mycobacterium kansasii. The best activity against M. tuberculosis was found for O-{4-bromo-2-[(3,4-dichlorophenyl)carbamoyl]phenyl} O,O-diethyl phosphorothioate (minimum inhibitory concentration of 4 µM). The highest activity against nontuberculous mycobacteria was exhibited by O-(5-chloro-2-{[4-(trifluoromethyl)phenyl]carbamoyl}-phenyl) O,O-diethyl phosphorothioate with MIC values from 16 µM. Prepared thiophosphates were also evaluated against acetylcholinesterase from electric eel and butyrylcholinesterase from equine serum. Their inhibitory activity was compared to that of the known cholinesterases inhibitors galanthamine and rivastigmine. All tested compounds showed a higher (for AChE inhibition) and comparable (for BChE inhibition) activity to that of rivastigmine, with IC50s within the 8.04 to 20.2 µM range. View Full-Text
Keywords: antimycobacterial activity; in vitro acetylcholinesterase inhibition; in vitro butyrylcholinesterase inhibition; salicylanilide; thiophosphates antimycobacterial activity; in vitro acetylcholinesterase inhibition; in vitro butyrylcholinesterase inhibition; salicylanilide; thiophosphates
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Vinšová, J.; Krátký, M.; Komlóová, M.; Dadapeer, E.; Štěpánková, Š.; Vorčáková, K.; Stolaříková, J. Diethyl 2-(Phenylcarbamoyl)phenyl Phosphorothioates: Synthesis, Antimycobacterial Activity and Cholinesterase Inhibition. Molecules 2014, 19, 7152-7168.

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