204254-79-5Relevant academic research and scientific papers
Synthesis of p-coumaroylquinic acids and analysis of their interconversion
Gutiérrez Ortiz, Anggy Lusanna,Berti, Federico,Navarini, Luciano,Monteiro, Angelo,Resmini, Marina,Forzato, Cristina
, p. 419 - 427 (2017/03/23)
The synthesis of four isomers of p-coumaroylquinic acids was performed by esterification of p-acetylcoumaroylchloride with a suitably protected (?)-quinic acid. All isomers have been characterized by means of NMR spectroscopy and circular dichroism. Acyl migration was observed in the synthesis of 3-O-p-coumaroylquinic acid and 4-O-p-coumaroylquinic acid. Calculations on the most stable conformations of all isomers have also been performed to explain the acyl migration observed during the synthesis procedure.
METHOD FOR PREVENTING OR TREATING ARRHYTHMIA, METHOD FOR PREVENTING OR TREATING ATRIAL FIBRILLATION, MODEL OF SUSTAINED ATRIAL FIBRILLATION, METHOD FOR PRODUCING THE MODEL, AND METHOD FOR SCREENING FOR ATRIAL FIBRILLATION INHIBITOR
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Paragraph 0092, (2014/03/24)
A method for preventing or treating atrial fibrillation, including: administering, to an individual, an atrial fibrillation inhibitor containing a compound expressed by one of the following Structural Formulas (I) to (VI) or a pharmacologically acceptable salt thereof: where in the Structural Formula (III), Gluc refers to glucuronic acid,
Syntheses of 3-, 4-, and 5-O-feruloylquinic acids
Dokli, Irena,Navarini, Luciano,Hamersak, Zdenko
, p. 785 - 790 (2013/08/23)
The efficient synthesis of 3-, 4-, and 5-O-feruloylquinic acids starting from d-(-)-quinic acid is described. Esterification of suitably protected quinic acid derivatives with 3-(4-acetoxy-3-methoxyphenyl)-acryloyl chloride and subsequent hydrolysis of al
Industrial synthesis of the key precursor in the synthesis of the anti-influenza drug oseltamivir phosphate (Ro 64-0796/002, GS-4104-02): Ethyl (3R,4S,5S)-4,5-epoxy-3-(1-ethyl-propoxy)-cyclohex-1 -ene-1 -carboxylate
Federspiel, Muriel,Fischer, Rolf,Hennig, Michael,Mair, Hans-Jürgen,Oberhauser, Thomas,Rimmler, G?sta,Albiez, Thomas,Bruhin, Jürg,Estermann, Heinrich,Gandert, Carsten,G?ckel, Volker,G?tz?, Stephan,Hoffmann, Ursula,Huber, Gabriel,Janatsch, Günter,Lauper, Stephan,R?ckel-St?bler, Odette,Trussardi, Rene,Zwahlen, Andreas G.
, p. 266 - 274 (2013/09/08)
Starting from (-)-quinic acid, the title compound was synthesized in seven chemical steps and an overall yield of 35-38%. The route of the improved Gilead synthesis was not changed. However, significant improvements in each step led to a doubled overall yield, a 30% reduction in the number of unit operations, and an excellent quality (≥99%) of the resulting epoxide. A highly regioselective method for the dehydration of a quinic acid to a shikimic acid derivative and for the reduction of a cyclic ketal was found. Alternatively, the title compound was synthesized in six chemical steps and 63-65% yield from commercially available (-)-shikimic acid. Compared to the optimized quinic acid route, the production time was reduced by about 50%. The quality of epoxide produced from either natural product was equivalent. Therefore (-)-shikimic acid is the preferred raw material. The absolute configuration of the epoxide was determined by X-ray single crystal structure analysis and it was demonstrated that the epoxide was stereo-isomerically pure.
