19961-72-9

Upstream product

• 591-27-5 m-Hydroxyaniline 
• 13683-89-1 methyl N-(3-hydroxyphenyl)carbamate 
• 103-71-9 phenyl isocyanate 

Downstream Products

• 76339-76-9 CH₃OC(O)N(SCFCl₂)C₆H₄OC(O)N(SCFCl₂)C₆H₅ 
• 37792-43-1 Acetyl-phenyl-carbamic acid 3-(acetyl-methoxycarbonyl-amino)-phenyl ester 

Relevant academic research and scientific papers

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

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 O-acylating phenol derivatives and acylating compositions for this purpose

A process is disclosed for preparing a carbamic acid phenyl ester of the formula (I) STR1 wherein R is alkyl having 1 to 8 carbon atoms, aryl, cycloalkyl having 5 or 6 carbon atoms, or aralkyl having 7 to 16 carbon atoms, wherein the aryl, cycloalkyl or aralkyl is unsubstituted or substituted by at least one alkyl group having 1 to 8 carbon atoms; R1 is hydrogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, cyanomethyl, 1,3-dioxolan-2-yl, or carboalkoxyamino wherein the alkoxy group contains 1 to 4 carbon atoms; R2 is hydrogen, halogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms; or R1 and R2 form together a carbocyclic ring or a heterocyclic ring fused to the phenyl ring wherein the carbocyclic ring of the heterocyclic ring is unsubstituted or substituted by at least one alkyl having 1 to 8 carbon atoms, which comprises acylating a phenol of the formula (II) STR2 with a compound of the formula (IV) STR3 in the presence of a base. The compounds obtained are valuable intermediates.