23294-39-5Relevant academic research and scientific papers
The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors
Minkkilae, Anna,Myllymaeki, Mikko J.,Saario, Susanna M.,Castillo-Melendez, Joel A.,Koskinen, Ari M.P.,Fowler, Christopher J.,Leppaenen, Jukka,Nevalainen, Tapio
experimental part, p. 2994 - 3008 (2009/10/10)
A series of para-substituted phenolic N-alkyl carbamates were evaluated for their FAAH and MGL inhibitory activities. The compounds were generally selective for FAAH, with IC50 values in the nM range, whereas inhibition of MGL required concentrations three orders of magnitude higher. The most potent compounds, dodecylcarbamic acid 4-(4,5-dihydrothiazol-2-yl)phenyl (12) and 4-(1,2,3-thiadiazol-4-yl)phenyl (26) esters, inhibited FAAH and MGL with IC50 values at the low-nanomolar (IC50s; 0.0063 and 0.012 μM) and the low-micromolar ranges (IC50s; 2.1 and 1.0 μM), respectively. Compound 26 also inhibited both FAAH-dependent AEA uptake and AEA hydrolysis (IC50; 0.082 μM) by intact RBL2H3 cells, and could also reduce 2-AG hydrolysis by these cells at concentrations ≥0.030 μM.
Synthesis of alkyl N-(C-nitrosoaryl)carbamates and some reactions thereof
Velikorodov
, p. 233 - 239 (2007/10/03)
Reactions of alkyl N-phenylcarbamates, m-di(methoxycarboxyamido)benzene, and methyl N-(o-tolyl)carbamate with nitrosylsulfuric acid in glacial acetic acid afford N-(C-nitrosoaryl)carbamates; under these conditions tert-bulyl N-phenylcarbamate suffers decarboxylation, methyl N-(p-tolyl)-, methyl N-(p-methoxyphenyl)carbamates, o-and p-di(methoxycarboxyamido)benzenes are nitrated, and isomeric methyl N-nitrophenylcarbamates and methyl N-(p-bromophenyl)carbamate do not react. The reduction of N-(C-nitrosoaryl)carbamates with dithionite afforded the corresponding aminocarbamates; the oxidation with nitric acid yielded carbamate nitro derivatives; the condensation with aniline and benzylpyridinium chloride resulted in carbamate derivatives of azobenzene and phenylnitron.
