1673-08-1Relevant academic research and scientific papers
Biomass derived β-cyclodextrin-SO3H as a solid acid catalyst for esterification of carboxylic acids with alcohols
Thombal, Raju S.,Jadhav, Amol R.,Jadhav, Vrushali H.
, p. 12981 - 12986 (2015/02/19)
A novel β-cyclodextrin-SO3H carbon based solid acid catalyst was prepared in a convenient and ecofriendly manner and was characterized using FTIR, PXRD, EDAX and NH3TPD to illustrate that the carbon material has been functionalized with -SO3H, -COOH and -OH groups. The catalyst was studied for esterification of various carboxylic acids and alcohols under solvent free conditions and showed excellent catalytic performance and gave good yields of esters in the range 78-99% at 70°C. No solvent was used either for catalyst preparation nor for esterification reaction. The catalyst can be easily recovered by simple filtration and reused for subsequent three runs without any significant impact on yields of products. The main advantage of this methodology is easy and ecofriendly catalyst preparation, easy catalyst separation, practical simplicity, safe reaction conditions, recyclable catalyst and high product yields.
A novel aromatic carbocation-based coupling reagent for esterification and amidation reactions
Nguyen, Thanh V.,Lyons, Demelza J.M.
supporting information, p. 3131 - 3134 (2015/06/17)
A novel tropylium-based coupling reagent has been developed to facilitate the synthesis of a series of esters, amides, lactones and peptides under mild reaction conditions. Remarkably, this reagent can be used in catalytic amounts in conjunction with a sacrificial reagent, offering a new and efficient method for nucleophilic coupling reactions of carboxylic acids.
Synthesis and biological evaluation of new potential inhibitors of N-acylethanolamine hydrolyzing acid amidase
Saturnino, Carmela,Petrosino, Stefania,Ligresti, Alessia,Palladino, Chiara,Martino, Giovanni De,Bisogno, Tiziana,Marzo, Vincenzo Di
supporting information; experimental part, p. 1210 - 1213 (2010/05/19)
N-Acylethanolamines, including N-palmitoyl-ethanolamine (PEA), are hydrolyzed to the corresponding fatty acids and ethanolamine by fatty acid amide hydrolase (FAAH). Recently, N-acylethanolamine-hydrolyzing acid amidase (NAAA) was identified as being able to specifically hydrolyze PEA. In order to find selective and effective inhibitors of this enzyme, we synthesized and screened several amides, retroamides, esters, retroesters and carbamates of palmitic acid (1-21) and esters with C15 and C17 alkyl chains (22-27). Cyclopentylhexadecanoate (13) exhibited the highest inhibitory activity on NAAA (IC50 = 10.0 μM), without inhibiting FAAH up to 50 μM. Compound 13 may become a useful template to design new NAAA inhibitors.
Esters, retroesters, and a retroamide of palmitic acid: Pool for the first selective inhibitors of N-palmitoylethanolamine-selective acid amidase
Vandevoorde, Séverine,Tsuboi, Kazuhito,Ueda, Natsuo,Jonsson, Kent-Olov,Fowler, Christopher J.,Lambert, Didier M.
, p. 4373 - 4376 (2007/10/03)
Cyclohexyl hexadecanoate, hexadecyl propionate, and N-(3-hydroxypropionyl)pentadecanamide, respectively ester, retroester, and retroamide derivatives of N-palmitoylethanolamine, represent the first selective inhibitors of "N-palmitoylethanolamine hydrolase" described so far. These compounds are devoid of affinity for CB1 and CB 2 receptors and characterized by high percentages of inhibition of N-palmitoylethanolamine-selective acid amidase (84.0, 70.5, and 76.7% inhibition at 100 μM, respectively) with much lower inhibitory effect on either fatty acid amide hydrolase or the uptake of anandamide.
