13684-56-5Relevant articles and documents
Synthesis and characterization of new inhibitors of cholinesterases based on N-phenylcarbamates: In vitro study of inhibitory effect, type of inhibition, lipophilicity and molecular docking
Vor?áková, Katarína,Májeková, Magdaléna,Horáková, Eva,Drabina, Pavel,Sedlák, Milo?,?těpánková, ?árka
, p. 280 - 289 (2018/04/06)
Based on current treatment of Alzheimer's disease, where the carbamate inhibitor Rivastigmine is used, two series of carbamate derivatives were prepared: (i) N-phenylcarbamates with additional carbamate group (1–12) and (ii) N-phenylcarbamates with monosaccharide moiety (13–24). All compounds were tested for the inhibitory effect on both of the cholinesterases, electric eel acetylcholinesterase (eeAChE) and butyrylcholinesterase from equine serum (eqBChE) and the inhibitory activity (expressed as IC50 values) was compared with that of the established drugs Galanthamine and Rivastigmine. The compounds with two carbamate groups 1–12 revealed higher inhibitory efficiency on both cholinesterases in compared with monosaccharide derived carbamates 13–24 and with Rivastigmine. The significant decrease of inhibitory efficiency on eqBChE (also for eeAChE but in less manner) was observed after deacetalization of monosaccharide. Moreover, the type of inhibitory mechanism of five chosen compounds was studied. It was found, that compounds with two carbamate groups act presumably via a mixed inhibitory mechanism and the compounds with monosaccharide moiety act as non-competitive inhibitors. The lipophilicity of tested compounds was determined using partition coefficient. Specific positions of the inhibitors in the binding sites of cholinesterases were determined using molecular modeling and the results indicate the importance of phenylcarbamate orientation in the catalytic gorges of both enzymes.
Process for the preparation of herbicidally active phenyl carbamates
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, (2008/06/13)
Herbicidally active substituted phenyl carbamates I STR1 in which R1 represents a C1 -C6 alkyl group, a C3 -C6 cycloalkyl group or an aryl group, which aryl group may be substituted by a halogen atom and/or a C1 -C6 alkyl group and/or a trifluoromethyl group, and R2 represents a C1 -C6 alkyl, C2 -C6 alkenyl or C2 -C6 alkynyl group that may be substituted by a terminal halogen atom, are prepared by reacting N-hydroxyphenyl carbamates II STR2 with either isocyanates R1 --N=C=O or amino chlorides R1 --NH--COCl in an aqueous medium thus avoiding the use of organic solvents. The end product I may be extracted from the aqueous slurry into a water-immiscible solvent. The N-hydroxyphenyl carbamates II can be prepared by reacting 3-aminophenol with chloroformates in an aqueous medium, and the resulting product may be reacted in situ, without isolation, with isocyanates, in the same reaction vessel. Stabilized herbicidal compositions containing compounds I may be prepared by suspending the compounds I in a liquid phase comprising one or more oily components and one or more surfactants.
