126519-80-0Relevant academic research and scientific papers
Discovery and SAR study of hydroxyacetophenone derivatives as potent, non-steroidal farnesoid X receptor (FXR) antagonists
Liu, Peng,Xu, Xing,Chen, Lili,Ma, Lei,Shen, Xu,Hu, Lihong
, p. 1596 - 1607 (2014/03/21)
Compound 1 (IC50 = 35.2 ± 7.2 μM), a moderate FXR antagonist was discovered via high-throughput screening. Structure-activity relationship studies indicated that the shape and the lipophilicity of the substituents of the aromatic ring affect the activity dramatically, increasing the shape and the lipophilicity of the substituents of the aromatic ring enhances the potency of FXR antagonists. Especially, when the OH at C2 position of the aromatic ring was replaced by the OBn substituent (analog 2b), its activity could be improved to IC50 = 1.1 ± 0.1 μM. Besides, the length of the linker and the tetrazole structure are essential for retaining the activity.
Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, sex pheromone components of the Lyclene dharma dharma moth, from the enantiomers of citronellal
Shikichi, Yasumasa,Mori, Kenji
, p. 1943 - 1951 (2013/01/15)
The enantiomers of citronellal were converted to all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2- octadecanone, the female-produced sex pheromone components of the Lyclene dharma dharma moth. Three wellestablished procedures, the Wittig reaction, alkylation of alkynes, and acetoacetic ester synthesis, were employed for the carbon-carbon bond formation to connect the building blocks.
Towards the development of new subtype-specific muscarinic receptor radiopharmaceuticals - Radiosynthesis and ex vivo biodistribution of [ 18F]3-(4-(2-(2-(2-fluoroethoxy)ethoxy)ethylthio)-1,2, 5-thiadiazol-3-yl)-1-methyl-1,2,5,6-tetrahydropyrid
Van Oosten, Erik M.,Wilson, Alan A.,Mamo, David C.,Pollock, Bruce G.,Mulsant, Benoit H.,Houle, Sylvain,Vasdev, Neil
, p. 1222 - 1232 (2011/02/24)
Muscarinic receptors have been implicated in neurological disorders including Alzheimer's disease, Parkinson's disease, and schizophrenia. Nineteen derivatives of thiadiazolyltetrahydropyridine (TZTP), a core that has previously shown high affinities towa
Synthesis of chiral 18-crown-6 ethers containing lipophilic chains and their enantiomeric recognition of chiral ammonium picrates
Colera, Manuel,Costero, Ana M.,Gavina, Pablo,Gil, Salvador
, p. 2673 - 2679 (2007/10/03)
Four new chiral 18-crown-6 ethers have been prepared to be used in enantiomeric recognition and extraction. The influence of the lipophilic character and bulkiness of the substituents on the complexation of different chiral ammonium picrates in CD3CN has been evaluated. Racemic aqueous solutions of the ammonium salts have been enriched in one enantiomer after extraction experiments, and the enantiomeric excesses have been calculated.
Asymmetric michael reactions on polymeric support: Auxiliary immobilization and stereoselective construction of quaternary stereocenters
Kreidler, Burkard,Baro, Angelika,Christoffers, Jens
, p. 5339 - 5348 (2007/10/03)
Several strategies for the immobilization of a L-valine-derived auxiliary on a Merrifield resin and on poly(ethylene glycol) are reported. The latter is shown to work excellently in asymmetric copper(II)-catalyzed Michael reactions of cyclic β-oxo esters 2 with methyl vinyl ketone (4), yielding the corresponding addition products 5 with quaternary stereocenter in selectivities of 97-99 % ee. The PEG-supported auxiliary 1d can be precipitated from diethyl ether solutions and reused. A sulfur-containing β-oxo ester 2c was prepared in 92 % yield by a DMAP-catalyzed transesterification method in order to detect enamine formation on solid support. The sulfur content can be used as an additional parameter in combustion analysis and therefore, may act as a diagnostic probe for enamine formation. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Silver(I) oxide-mediated facile and practical sulfonylation of alcohols
Bouzide, Abderrahim,LeBerre, Nicolas,Sauvé, Gilles
, p. 8781 - 8783 (2007/10/03)
Primary and secondary alcohols were efficiently sulfonylated in the presence of silver(I) oxide and potassium iodide in dichloromethane. The sulfonylation occurs under mild, neutral reaction conditions. The ease of isolation of the final product presents a marked advantage over the known methodologies.
Enzyme-mediated preparation of optically active 1,2-diols bearing a long chain: Enantioselective hydrolysis of cyclic carbonates
Shimojo, Megumi,Matsumoto, Kazutsugu,Hatanaka, Minoru
, p. 9281 - 9288 (2007/10/03)
A new entry for the efficient preparation of optically active 1,2-diols having a long aliphatic chain via an enzymatic reaction is disclosed. PPL catalyzes the hydrolysis of a racemic five-membered cyclic carbonate, 4-(%benzyloxy)heptyl-1,3-dioxolan-2-one (2a), with high enantioselectivity to produce the optically active (R)-2a and (S)-9-benzyloxynonane-1,2-diol (3a) in excellent yields. The reaction is applicable to the substrates with a longer chain (10-benzyloxydecyl (3b) and 13-benzyloxytridecyl group (3c)). Optically pure (S)-(+)-8hydroxyhexadecanoic acid (1), a biologically active natural compound with a chiral long aliphatic part, is effectively synthesized starting from (R)-3-(7-benzyloxy)heptyl-2-oxirane (9), which is converted from both enantiomers of 3a. (C) 2000 Elsevier Science Ltd.
Synthesis of optically active diols bearing a long chain via enzymatic hydrolysis of cyclic carbonates
Matsumoto, Kazutsugu,Shimojo, Megumi,Hatanaka, Minoru
, p. 1151 - 1152 (2007/10/03)
PPL catalyzes the hydrolysis of racemic five-membered cyclic carbonates bearing a long chain with high enantioselectivity. Optically pure (S)-(+)-8-hydroxyhexadecanoic acid is effectively synthesized starting from (R)-4-(7-benzyloxy)heptyl-1,3-dioxolan-2-one and (S)-9-benzyloxynonane-1,2-diol, which are prepared via an enzymatic reaction.
Pheromone Synthesis, CLX. A New Synthesis of the Oviposition-Deterring Pheromone of the European Cherry Fruit Fly Rhagoletis cerasi L.
Mori, Kenji,Qian, Zhao-Hui
, p. 291 - 296 (2007/10/02)
A new synthesis of the ammonium salt 1c of (8RS,15R)-Ntaurine, the oviposition-deterring pheromone of the European cherry fruit fly Rhagoletis cerasi L., was achieved by starting from 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide (2), taurine (4), ethyl (R)-3-hydroxybutanoate (5), propargyl alcohol (6), methyl acetoacetate (7), and 1,6-hexanediol (8). - Key Words: Fruit fly, European cherry / Glycosides / Pheromones / Oviposition-deterring pheromone / Rhagoletis cerasi L.
