20576-83-4Relevant articles and documents
Cleavage of Carboxylic Esters by Aluminum and Iodine
Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan
, p. 4254 - 4261 (2021/03/09)
A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.
Synthesis and structure - Activity relationships of N -(2-Oxo-3-oxetanyl) amides as N -acylethanolamine-hydrolyzing acid amidase inhibitors
Solorzano, Carlos,Antonietti, Francesca,Duranti, Andrea,Tontini, Andrea,Rivara, Silvia,Lodola, Alessio,Vacondio, Federica,Tarzia, Giorgio,Piomelli, Daniele,Mor, Marco
scheme or table, p. 5770 - 5781 (2010/10/20)
The fatty acid ethanolamides (FAEs) are a family of bioactive lipid mediators that include the endogenous agonist of peroxisome proliferator- activated receptor-α, palmitoylethanolamide (PEA). FAEs are hydrolyzed intracellularly by either fatty acid amide hydrolase or N-acylethanolamine- hydrolyzing acid amidase (NAAA). Selective inhibition of NAAA by (S)-N-(2-oxo-3-oxetanyl)-3-phenylpropionamide [(S)-OOPP, 7a] prevents PEA degradation in mouse leukocytes and attenuates responses to proinflammatory stimuli. Starting from the structure of 7a, a series of β-lactones was prepared and tested on recombinant rat NAAA to explore structure-activity relationships (SARs) for this class of inhibitors and improve their in vitro potency. Following the hypothesis that these compounds inhibit NAAA by acylation of the catalytic cysteine, we identified several requirements for recognition at the active site and obtained new potent inhibitors. In particular, (S)-N-(2-oxo-3-oxetanyl)biphenyl-4-carboxamide (7h) was more potent than 7a at inhibiting recombinant rat NAAA activity (7a, IC50 = 420 nM; 7h, IC50 = 115 nM) in vitro and at reducing carrageenan-induced leukocyte infiltration in vivo.
Molecular structure and smectic properties. Part 1. The effect of linkages on smectic A thermal stability in three aromatic ring compounds linked by ester groups
Sakurai, Yoshiaki,Takenaka, Shunsuke,Miyake, Hajime,Morita, Hidefumi,Ikemoto, Tetsuya
, p. 1199 - 1204 (2007/10/02)
The thermal properties of phenyl 4-(4-alkoxybenzoyloxy)benzoates (1), 4-alkoxyphenyl 4-benzoyloxybenzoates (2), 4-(4-alkoxybenzoyloxy) benzoyloxyxylenes (3), and phenyl 4-(4-alkoxyphenoxycarbonyl)benzoates (4) have been examined. In spite of the structural similarity, the smectic nature of the series is quite different. Series (1) shows a stable smectic A phase starting with the hexyloxy homologue. Series (2) and (3) do not show any smectic phases, and the potential smectic stabilities evaluated from the binary phase diagrams are quite low. Although series (4) shows no smectic phase because of higher melting points, this series intrinsically possesses a smectic A nature, where the potential smectic A - nematic transition temperatures are as high as those of series (1). The difference in the smectic nature for these four series is discussed in terms of the geometrical and electrocstatic properties of the molecules, and a new basis for the thermal stability of the smectic A phase has been proposes.
