120787-40-8Relevant articles and documents
Structure-activity relationship of a series of inhibitors of monoacylglycerol hydrolysis - Comparison with effects upon fatty acid amide hydrolase
Cisneros, José Antonio,Vandevoorde, Séverine,Ortega-Gutiérrez, Silvia,Paris, Clément,Fowler, Christopher J.,López-Rodríguez, María L.
, p. 5012 - 5023 (2007)
A series of 32 heterocyclic analogues based on the structure of 2-arachidonoylglycerol (2-AG) were synthesized and tested for their ability to inhibit monoacylglycerol lipase and fatty acid amide hydrolase activities. The designed compounds feature a hydrophobic moiety and different heterocyclic subunits that mimic the glycerol fragment. This series has allowed us to carry out the first systematic structure-activity relationship study on inhibition of 2-AG hydrolysis. The most promising compounds were oxiran-2-ylmethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate (1) and tetrahydro-2H-pyran-2- ylmethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate (5). They inhibited cytosolic 2-oleoylglycerol (2-OG) hydrolysis completely (IC50 values of 4.5 and 5.6 μM, respectively). They also blocked, albeit less potently, 2-OG hydrolysis in membrane fractions (IC50 values of 19 and 26 μM, respectively) and anandamide hydrolysis (IC50 values of 12 and 51 μM, respectively). These compounds will be useful in delineating the importance of the cytosolic hydrolytic activity in the regulation of 2-AG levels and, hence, its potential as a target for drug development.
The synthesis of densely functionalised α-acyloxy enaminals and enaminones: Via a novel homogeneous silver(i) catalysed rearrangement
Keskar, Kunal,Zepeda-Velazquez, Carlos,Dokuburra, Chanti Babu,Jenkins, Hilary A.,McNulty, James
, p. 10868 - 10871 (2019/09/16)
A synthesis of densely functionalised α-acyloxy enaminals and enaminones via a novel homogeneous silver(i) catalyzed rearrangement of 1-acyloxy-3-azido ketones is reported. This silver catalyzed reaction involves an internal redox process comprised of fou
A Straightforward Conversion of Activated Amides and Haloalkanes into Esters under Transition-Metal-Free Cs 2 CO 3 /DMAP Conditions
Chen, Liuqing,Gu, Ying,Jian, Junsheng,Liu, Yueping,Miao, Liqiong,Wang, Zijia,Zeng, Zhuo
supporting information, p. 4078 - 4084 (2019/10/28)
The esterification of activated amides, N -acylsaccharins, under transition-metal-free conditions with good functional group tolerance has been developed, resulting in C-N cleavage leading to efficient synthesis of a variety of esters in moderate to good yields. This work demonstrates that esterification may proceed by using simple N -acylsaccharins, haloalkanes, and Cs 2 CO 3 as oxygen source.
Quaternary Alkyl Ammonium Salt-Catalyzed Transformation of Glycidol to Glycidyl Esters by Transesterification of Methyl Esters
Tanaka, Shinji,Nakashima, Takuya,Maeda, Toshie,Ratanasak, Manussada,Hasegawa, Jun-Ya,Kon, Yoshihiro,Tamura, Masanori,Sato, Kazuhiko
, p. 1097 - 1103 (2018/02/14)
Catalytic transformation of glycidol while maintaining its epoxide moiety intact is challenging because the terminal epoxide that interacts with the hydroxyl group via a hydrogen bond is labile for the ring-opening reaction. We found that a quaternary alkyl ammonium salt catalyzes the selective transformation of glycidol to glycidyl esters by transesterification of methyl esters. The developed method can be applied to the synthesis of multiglycidyl esters, which are valuable epoxy resin monomers. Mechanistic studies revealed the formation of a binding complex of glycidol and quaternary alkyl ammonium salt in a nonpolar solvent and the generation of the alkoxide anion as a catalyst through the ring-opening reaction of the epoxide. Computational studies of the reaction mechanism indicated that the alkoxide anion derived from glycidol tends to abstract the proton of another glycidol rather than work as a nucleophile, initiating the catalytic transesterification. Payne rearrangement of the deprotonated glycidol, which produces a destabilized base that promotes nonselective reactions, is energetically unfavorable due to the double hydrogen bond between the anion and diol. The minimal interaction between the quaternary alkyl ammonium cation and the epoxide moiety inhibited the random ring-opening pathway leading to polymerization.
