59834-04-7Relevant 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.
4-(2-Hydroxyaryl)-1,2,3-thiadiazoles as a source of 2-benzofuranthiolates
Petrov,Dehaen,Abramov,Abramova,Androsov
, p. 1510 - 1518 (2007/10/03)
Following the Hurd-Mori procedure, 4-(2-hydroxyaryl)-1,2,3-thiadiazoles were synthesized from o-hydroxyacetophenones. Treatment of the products with bases gives 2-benzofuranthiolates which can be involved in alkylation and arylation reactions.
A general synthesis of benzofuran-2-thiolates via intramolecular addition of phenolates to alkynethiolates
D'Hooge, Bart,Smeets, Stefan,Toppet, Suzanne,Dehaen, Wim
, p. 1753 - 1754 (2007/10/03)
4-(ortho-Hydroxyaryl)-1,2,3-thiadiazoles can be transformed into benzofuran-2-thiolates via an intramolecular cyclization.
Synthesis of o-acylarylcarboxylic esters: A new replacement of phenolic hydroxyl by a carbonyl group
Katritzky,Kotali
, p. 6781 - 6784 (2007/10/02)
A wide variety of the title esters are prepared in good yields via a new two step replacement of phenolic hydroxyl by an ethoxycarbonyl group.
