- Lipophilic amines as potent inhibitors of N-acylethanolamine-hydrolyzing acid amidase
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N-Acylethanolamines (NAEs) including N-arachidonoylethanolamine (anandamide) and N-palmitoylethanolamine are endogenous lipid mediators. These molecules are degraded to the corresponding fatty acids and ethanolamine by fatty acid amide hydrolase (FAAH) or NAE-hydrolyzing acid amidase (NAAA). Lipophilic amines, especially pentadecylamine (2c) and tridecyl 2-aminoacetate (11b), were found to exhibit potent NAAA inhibitory activities (IC50 = 5.7 and 11.8 μM), with much weaker effects on FAAH. These simple structures would provide a scaffold for further improvement in NAAA inhibitory activity.
- Yamano, Yumiko,Tsuboi, Kazuhito,Hozaki, Yuki,Takahashi, Kiyohiro,Jin, Xing-Hua,Ueda, Natsuo,Wada, Akimori
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p. 3658 - 3665
(2012/07/28)
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- Process for production of ether amine
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Disclosed herein are a process for producing an ether amine(3), which comprises reacting a primary or secondary alcohol(1),ROH, with acrylonitrile in an amount of 0.8 to 1.2 equivalents of the alcohol(1) in the presence of an alkali metal hydroxide in an amount of not less than 0.01 part by weight, but less than 0.05 part by weight per 100 parts by weight of the alcohol(1) to obtain an alkyloxypropionitrile(2),and then adding water to the reaction system without removing the alkali metal hydroxide therefrom and effecting hydrogenation using a hydrogenation catalyst:ROH(1)+ CH2=CHCN, ROCH2CH2CH2CN(2), ROCH2CH2CH2NH2(3) wherein R denotes a linear or branched alkyl or alkenyl group having 6 to 24 carbon atoms. Also disclosed are a process for producing an ether tertiary amine (5), R-O-CH2-CH2-CH2-N(CH2R1)2, which comprises adding an aldehyde to the resulting ether amine(3) in the presence of a metal catalyst or a Raney nickel catalyst, and a process for producing an ether quaternary ammonium salt (6), R-O-CH2-CH2-CH2-N(CH2R1)2(R2), which comprises reacting a quaternizing agent with the ether tertiary amine(5).
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Example 2; comparative 2
(2008/06/13)
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- Aldose epimerization by Ni(II): effect of ether-containig alkylenediamine ligands
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Several N-substituted ethylenediamine (en) Ni(II) derivatives containing ether linkages were prepared in order to study the effect of ligand structure on C-2 epimerization of aldohexoses.The reagent consisted of a Ni(II)-alkyenediamine derivative in methanol.The presence of ether linkages in the ligand increased the solubilty of the complexes, and resulted in an increase in the rate of epimerization.Epimerization occured rapidly under mild conditions, and the same equilibrium point was reached regardless of whether the reaction was started from glucose or mannose.Among the ligands studied, N,N'-dialkylethylenediamine was the most effective in C-2 epimerization.
- Osanai, Shuichi,Inaba, Kiyoshi,Yoshikawa, Sadao
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p. 289 - 295
(2007/10/02)
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