26420-23-5Relevant articles and documents
Azo chromophore functionalized polythiophenes. Synthesis and nonlinear optical properties
Zagorska,Gase,Kajzar,Raimond,Kulszewicz-Bajer,Pron
, p. 493 - 501 (2000)
New polythiophene derivatives containing azo dye side group were prepared via copolymerization of 3-alkylthiophenes and Disperse Red 1 substituted thiophenes. The presence of chromophore groups in the polymers was confirmed by NMR and FTIR spectroscopies as well as by elemental analysis. The obtained soluble polymers were processed into thin films by spin coating technique and their nonlinear optical properties were studied by the optical second harmonic generation technique and by quadratic electro-optic Kerr effect. The second order nonlinear optical coefficients are: dsp = 6.8 pm/V and dpp = 28.3 pm/V at 1064 nm fundamental wavelength. The quadratic electro-optic Kerr coefficient is about three times larger for the unfunctionalized polymer than for unfoncionalized.
Synthesis, biological evaluation, and structure activity relationship (SAR) study of pyrrolidine amide derivatives as: N -acylethanolamine acid amidase (NAAA) inhibitors
Zhou, Pan,Xiang, Lei,Zhao, Dongsheng,Ren, Jie,Qiu, Yan,Li, Yuhang
, p. 252 - 262 (2019/03/02)
N-Acylethanolamine acid amidase (NAAA) is one of the key enzymes involved in the degradation of fatty acid ethanolamides (FAEs), especially for palmitoylethanolamide (PEA). Pharmacological blockage of NAAA restores PEA levels, providing therapeutic benefits in the management of inflammation and pain. In the current work, we showed the structure-activity relationship (SAR) studies for pyrrolidine amide derivatives as NAAA inhibitors. A series of aromatic replacements or substituents for the terminal phenyl group of pyrrolidine amides were examined. SAR data showed that small lipophilic 3-phenyl substituents were preferable for optimal potency. The conformationally flexible linkers increased the inhibitory potency of pyrrolidine amide derivatives but reduced their selectivity toward fatty acid amide hydrolase (FAAH). The conformationally restricted linkers did not enhance the inhibitor potency toward NAAA but improved the selectivity over FAAH. Several low micromolar potent NAAA inhibitors were developed, including 4g bearing a rigid 4-phenylcinnamoyl group. Dialysis and kinetic analysis suggested that 4g inhibited NAAA via a competitive and reversible mechanism. Furthermore, 4g showed high anti-inflammatory activities in lipopolysaccharide (LPS) induced acute lung injury (ALI) model, and this effect was blocked by pre-treatment with the PPAR-α antagonist MK886. We anticipate that 4g (E93) will enable a new agent to treat inflammation and related diseases.
TRICYCLIC INHIBITORS OF FATTY ACID AMIDE HYDROLASE
-
Page/Page column 42, (2009/01/24)
A series of substituted oxazole compounds having an alpha keto side chain at the 2 position and an aromatic, heteroaromatic or heterocycle substituent at the 5 position are disclosed. These compounds exhibit inhibition of fatty acid amid hydrolase and are useful for treatment of malconditions involving that enzyme.
Structure-activity relationships of α-ketooxazole inhibitors of fatty acid amide hydrolase
Hardouin, Christophe,Kelso, Michael J.,Romero, F. Anthony,Rayl, Thomas J.,Leung, Donmienne,Hwang, Inkyu,Cravatt, Benjamin F.,Boger, Dale L.
, p. 3359 - 3368 (2008/02/13)
A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1-napthyl, K, - 2.6 nM), with 5hh (aryl -3-ClPh, Ki = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, Ki = 3 nM, or 13d, 2-position OH, Ki = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of >100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.
SYNTHESE ET ETUDE ELECTROCHIMIQUE D'ALCOOLS ET D'ESTERS DERIVES DE 3-ALKYL THIOPHENES
Blanchetiere, D.,Noyere, C.,Catel, J.,Andrieu, C. G.,Ebel, M.
, p. 93 - 102 (2007/10/03)
Starting from 3-bromothiophene, ω-(3-thienyl)alkan-1-ols and ω-(3-thienyl)alkyl esters are obtained.Electrochemical characteristics and polymerization are described and discussed.Key words: ω-(3-thienyl)alkanols and ω-(3-thienyl)alkyl esters, electrochemical polymerization.
