HPLC enantioseparation and absolute configuration of novel anti-inflammatory pyrrole derivatives.


:The assignment of the absolute configuration of novel anti-inflammatory pyrrole derivatives has been accomplished by a combined strategy based on independent physical methods. The key step of our stereochemical characterization approach is the production at mg-scale of enantiomerically pure forms by HPLC on Chiralpak IA stationary phase.






Biava M,Cirilli R,Fares V,Ferretti R,Gallinella B,La Torre F,Poce G,Porretta GC,Supino S,Villani C




Has Abstract


2008-06-01 00:00:00












  • Spontaneous resolution of 2,3-bis-fluoren-9-ylidenesuccinic acid induced by achiral guest inclusion.

    abstract::The racemic title host compound (1) formed homochiral inclusion crystals (conglomerate) of 1 with acetone, while heterochiral inclusion crystals (racemate) were obtained when complexed with ethyl acetate. Upon treatment of the homochiral inclusion crystals of 1 with gaseous acetyl chloride in the solid state, opticall...


    pub_type: 杂志文章


    authors: Tanaka K,Iwamoto T,Wada S,Frelek J,Caira MR

    更新日期:2006-08-01 00:00:00

  • Enantioselective reduction of ketones with borane catalyzed by tridentate amino alcohols derived from salicylaldehyde.

    abstract::In the presence of tridentate chiral ligand 4e, 99% e.e. value was obtained by asymmetric reduction of ethyl benzoylacetate with borane in toluene at 25 degrees C. Various ligands and reaction conditions were investigated to develop a reasonable mechanism that explains the experimental outcomes. ...


    pub_type: 杂志文章


    authors: Lee DS

    更新日期:2007-02-01 00:00:00

  • Chiroptical property tuning of supramolecular assemblies in polymer matrices.

    abstract::Chiroptical materials have received much attention in diverse fields for applications such as displays, sensors, smart memory devices, and catalysis. Here, we develop a simple fabrication method for polymer films with tunable chiroptical properties using small amounts of self-assembling fluorescent dye as an additive....


    pub_type: 杂志文章


    authors: Jintoku H,Ihara H

    更新日期:2020-05-01 00:00:00

  • Enantioselective HPLC determination of E-6087, a new COX-2 inhibitor, in human plasma: Validation and pharmacokinetic application.

    abstract::E-6087 is a nonsteroidal anti-inflammatory compound that selectively inhibits cyclooxygenase-2. Because E-6087 has a chiral center, this compound is a racemic mixture of two stereoisomers, (+)-(R)-E-6087 (E-6231) and (-)-(S)-E-6087 (E-6232). A normal-phase liquid-chromatographic method for the enantioselective determi...


    pub_type: 杂志文章


    authors: Salgado L,Encina G,Farran R,Puig S,Martínez L

    更新日期:2004-05-15 00:00:00

  • Tautomerism of 4-hydroxy-2,5-dimethyl-3(2H)-furanone: evidence for its enantioselective biosynthesis.

    abstract::Chiral natural flavor compounds exhibit characteristic enantiomeric excesses due to stereoselective, enzymatically catalyzed reactions during biogenesis. Although the enzymatic formation of the strawberry key flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF; Furaneol(R)) is anticipated, the naturally occurr...


    pub_type: 杂志文章


    authors: Raab T,Hauck T,Knecht A,Schmitt U,Holzgrabe U,Schwab W

    更新日期:2003-08-01 00:00:00

  • Direct asymmetric Michael addition of thioether-based aryl sulfanyl-propan-2-one to nitroalkenes catalyzed by a chiral amine-thiourea bifunctional organocatalyst.

    abstract::Although the organocatalytic direct asymmetric Michael reactions of carbonyl compounds to nitroalkenes have been investigated intensely, the Michael reaction of the thioether-based donors remains a rather undeveloped field. This work concerns the asymmetric Michael addition of aryl sulfanyl-propan-2-one to nitroalkene...


    pub_type: 杂志文章


    authors: Jiang X,Zhang B,Zhang Y,Lin L,Yan W,Wang R

    更新日期:2010-07-01 00:00:00

  • Configuration of heptopyranoside and heptofuranoside side chains: 2-anthroate, a powerful chromophore for exciton coupled CD.

    abstract::The absolute configuration of the acyclic side chain of heptopyranosides and heptofuranosides was determined by exciton coupled CD, employing the strongly fluorescent 2-anthroate chromophore. The usage of this chromophore offers significant improvements over previous chemical and spectroscopic procedures since its int...


    pub_type: 杂志文章


    authors: Akritopoulou-Zanze I,Nakanishi K,Stepowska H,Grzeszczyk B,Zamojski A,Berova N

    更新日期:1997-01-01 00:00:00

  • Evaluation of "click" binaphthyl chiral stationary phases by liquid chromatography.

    abstract::Two "click" binaphthyl chiral stationary phases were synthesized and evaluated by liquid chromatography. Their structures incorporate S-(-)-1,1'-binaphthyl moiety as the chiral selector and 1,2,3-triazole ring as the spacer. These chiral stationary phases (CSPs) allowed the efficient resolution for a wide range of rac...


    pub_type: 杂志文章


    authors: Yu H,Yin C,Jia C,Jin Y,Ke Y,Liang X

    更新日期:2012-05-01 00:00:00

  • Stereoselective chiral inversion of pantoprazole enantiomers after separate doses to rats.

    abstract::(+/-)-Pantoprazole ((+/-)-PAN), (+/-)-5-(difluoromethoxy)-2-[[3.4-dimethoxy-2-pyridinyl)methyl]sul finyl]- 1H-benzimidazole) is a chiral sulfoxide that is used clinically as a racemic mixture. The disposition kinetics of (+)-PAN and (-)-PAN given separately has been studied in rats. Serum levels of (+)- and (-)-PAN an...


    pub_type: 杂志文章


    authors: Masubuchi N,Yamazaki H,Tanaka M

    更新日期:1998-01-01 00:00:00

  • Plant and soil enantioselective biodegradation of racemic phenoxyalkanoic herbicides.

    abstract::The biodegradation of the chiral phenoxyalkanoic herbicides 2-(2,4-dichlorophenoxy)propionic aid (2,4-DP) and 2-(4-chloro-2-methylphenoxy)propionic acid (MCPP) was investigated using enantioselective HPLC and chiroptical detection. Racemic mixtures of 2,4-DP and MCPP were applied to three species of turf grass, four s...


    pub_type: 杂志文章


    authors: Schneiderheinze JM,Armstrong DW,Berthod A

    更新日期:1999-01-01 00:00:00

  • Spectroscopic studies on nicotine and nornicotine in the UV region.

    abstract::The UV absorption and electronic circular dichroism (ECD) spectra of (R)- and (S)-nicotine and (S)-nornicotine in aqueous solution were measured to a significantly lower wavelength range than previously reported, allowing the identification of four previously unobserved electronic transitions. The ECD spectra of the t...


    pub_type: 杂志文章


    authors: Clayton PM,Vas CA,Bui TT,Drake AF,McAdam K

    更新日期:2013-05-01 00:00:00

  • Enantioselective Friedel-Crafts reaction of indoles with trifluoroacetaldehyde catalyzed by Cinchona alkaloids.

    abstract::The first direct asymmetric synthetic preparation of trifluoro-1-(indol-3-yl)ethanols (TFIEs) is described by an enantioselective organocatalytic method from indoles and inexpensive trifluoroacetaldehyde methyl hemiacetal. The reaction is catalyzed by hydroquinine to produce TFIEs in an almost quantitative yield and w...


    pub_type: 杂志文章


    authors: Borkin DA,Landge SM,Török B

    更新日期:2011-09-01 00:00:00

  • Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism.

    abstract::Advances in the measurement, calculation, and application of vibrational circular dichroism (VCD) for the determination of absolute configuration are described. The purpose of the review is to provide an up-to-date perspective on the capability of VCD to solve problems of absolute stereochemistry for chiral molecules ...


    pub_type: 杂志文章


    authors: Freedman TB,Cao X,Dukor RK,Nafie LA

    更新日期:2003-11-01 00:00:00

  • Synthesis and pharmacological investigation of stereoisomeric muscarines.

    abstract::The synthesis of the eight stereoisomers of muscarine has been efficiently accomplished by utilizing the two enantiomers of lactic esters as starting material. The synthetic strategy is based on a SnCl4-catalyzed addition of allyltrimethylsilane to O-protected lactic aldehydes followed by an iodocyclization process. A...


    pub_type: 杂志文章


    authors: De Amici M,Dallanoce C,De Micheli C,Grana E,Dondi G,Ladinsky H,Schiavi G,Zonta F

    更新日期:1992-01-01 00:00:00

  • Synthesis of novel camphor-derived bifunctional thiourea organocatalysts.

    abstract::Synthesis and catalyst performance of 2,3- (types and ) and 2,8-disubstituted (type ) thiourea bifunctional organocatalysts was attempted. The synthesis of catalyst of type has, so far, not been realized, while catalysts of type , i.e., the 2,3-exo- and the 2-endo-3-exo-thiourea catalysts, were prepared in six steps s...


    pub_type: 杂志文章


    authors: Ričko S,Golobič A,Svete J,Stanovnik B,Grošelj U

    更新日期:2015-01-01 00:00:00

  • Enantioselective degradation of warfarin in soils.

    abstract::Environmental enantioselectivity information is important to fate assessment of chiral contaminants. Warfarin, a rodenticide and prescription medicine, is a chiral chemical but used in racemic form. Little is known about its enantioselective behavior in the environment. In this study, enantioselective degradation of w...


    pub_type: 杂志文章


    authors: Lao W,Gan J

    更新日期:2012-01-01 00:00:00

  • Research into the oxidation of abietic acid-derived enone with atmospheric oxygen.

    abstract::This work presents results of methyl 7-oxoabiet-13(14)-en-18-oate (3) self-oxidation with air-oxygen in the presence of various bases such as triethylamine or sodium t-butoxide. While under aerobic conditions, the use of sodium t-butoxide as a base results in the formation of four isomeric alcohols, an addition of tri...


    pub_type: 杂志文章


    authors: Masnyk M,Kuśmirek D,Trzybiński D,Frelek J

    更新日期:2020-04-01 00:00:00

  • Spectroscopic properties of the nonplanar amide group: a computational study.

    abstract::Experimental studies suggest that amide bond may significantly deviate from planar arrangement even in linear peptides and proteins. In order to find out the extent to which such deviation may influence principal amide spectroscopic properties, we conducted a computational study of nonplanar N-methylacetamide (NMA) co...


    pub_type: 杂志文章


    authors: Bednárová L,Malon P,Bour P

    更新日期:2007-11-01 00:00:00

  • Influence of endotoxin on the stereoselective pharmacokinetics of oxprenolol, propranolol, and verapamil in the rat.

    abstract::The influence of endotoxin-induced inflammation on the enantioselective pharmacokinetics of propranolol, oxprenolol, and verapamil, which bind to alpha 1-acid glycoprotein, was studied in the rat. The racemic mixtures were given orally. In the control animals, for propranolol and oxprenolol, the plasma concentrations ...


    pub_type: 杂志文章


    authors: Laethem ME,Belpaire FM,Wijnant P,Rosseel MT,Bogaert MG

    更新日期:1994-01-01 00:00:00

  • A new water soluble Zn-salophen derivative as a receptor for alpha-aminoacids: unexpected chiral discrimination.

    abstract::A new water soluble zinc-salophen complex with appended D-glucose moieties was synthesized and characterized. Its binding properties toward six aminoacids were investigated by UV-vis spectrophotometric titrations. Association constants showed to be unfavorably affected by increasing steric hindrance of the side chain....


    pub_type: 杂志文章


    authors: Dalla Cort A,De Bernardin P,Schiaffino L

    更新日期:2009-01-01 00:00:00

  • Chiral aggregates and asymmetric induction of the reduction of prochiral ketones.

    abstract::The aim of this work was to establish structure-reactivity relationships between chiral aggregates (micelles, vesicles, and "pseudo-micelles" of amphiphilic dendrimers) and asymmetric induction. In water, micelles or vesicles formed with sugar-headed surfactants gave less than 10% ee in the reduction of prochiral keto...


    pub_type: 杂志文章


    authors: Rico-Lattes I I,Schmitzer A,Perez E,Lattes A

    更新日期:2001-01-01 00:00:00

  • Structural Basis and Mechanism of Chiral Benzedrine Molecules Interacting With Third Dopamine Receptor.

    abstract::In order to investigate the chiral benzedrine molecules corresponding to their different characteristics in biochemical systems, we studied their interaction with D3 R using the docking method, molecular dynamic simulation, and quantum chemistry. The obtained results indicate that the active residues for R-benzedrine ...


    pub_type: 杂志文章


    authors: Wang M,Xie W,Li A,Xu S

    更新日期:2016-10-01 00:00:00

  • Natural alkaloids and synthetic relatives as chiral templates of the Orito's reaction.

    abstract::The enantioselective hydrogenation of methyl or ethyl pyruvate over cinchona-platinum catalyst system (Orito's reaction) is one of the most intensively studied heterogeneous catalytic asymmetric hydrogenation reactions. Studies aiming at systematic changes of the chiral template have played a crucial role in creating ...


    pub_type: 杂志文章,评审


    authors: Tálas E,Margitfalvi JL

    更新日期:2010-01-01 00:00:00

  • Stereoselective renal secretion of carbenicillin in rabbits: role of the organic anion transporter at the renal brush border membrane.

    abstract::Stereoselectivity in the renal secretion of carbenicillin (CBPC) was studied in rabbits. Significant renal secretion of CBPC was observed in vivo, with the secretion of the S-epimer being greater than that of the R-epimer. Stereoselective transport of CBPC was further studied in vitro using basolateral and brush borde...


    pub_type: 杂志文章


    authors: Itoh T,Nakaura H,Koyano S,Tsuda Y,Yamada H

    更新日期:1998-01-01 00:00:00

  • Stereospecific pH-dependent degradation kinetics of R- and S-naproxen-beta-l-O-acyl-glucuronide.

    abstract::The hydrolysis and acyl migration of biosynthetic S-naproxen-beta-l-O-acyl glucuronide (I) and R-naproxen-beta-l-O-acyl glucuronide (II) was followed by HPLC. Nine first-order kinetic rate constants for the hydrolysis and acyl migration between the beta-l-O-acyl glucuronide, its alpha/beta-2, alpha/beta-3-, alpha/beta...


    pub_type: 杂志文章


    authors: Mortensen RW,Sidelmann UG,Tjørnelund J,Hansen SH

    更新日期:2002-05-05 00:00:00

  • Four conformers characterized in allyl nitrite.

    abstract::Allyl nitrite, O=NOCH(2)CH=CH(2), can exist in conformations which include syn (S) and anti (A) configurations of O=N-O-C, anti or gauche (G) configurations of N-O-C-C, and syn or skew (Sk) configurations of O-C-C=C. Four of them have been observed and characterized by their microwave spectra and quantum chemical calc...


    pub_type: 杂志文章


    authors: Lee SG,Breeze L,Bohn RK,True NS

    更新日期:2002-02-01 00:00:00

  • Enantioselective separation of (±)-β-hydroxy-1,2,3-triazoles by supercritical fluid chromatography and high-performance liquid chromatography.

    abstract::This paper reports the enantioseparation of β-hydroxy-1,2,3-triazole derivatives, which present a broad range of biological properties, by supercritical fluid chromatography (SFC) and high-performance liquid chromatography techniques (HPLC). Polysaccharide-based chiral columns (cellulose and amylose) were used to eval...


    pub_type: 杂志文章


    authors: Alvarenga N,Porto ALM,Barreiro JC

    更新日期:2018-07-01 00:00:00

  • Discrimination of chiral guests by chiral channels: variable temperature studies by SXRD and solid state 13C NMR of the deoxycholic acid complexes of camphorquinone and endo-3-bromocamphor.

    abstract::3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid (deoxycholic acid DCA) is able to discriminate between the R- and S-enantiomers of camphorquinone and endo-(+)-3-bromocamphor and select only the S-enantiomers from a racemic mixture. DCA forms novel well ordered 1:1 adducts with (1S)-(+)-camphorquinone and (1S)-endo-(...


    pub_type: 杂志文章


    authors: Tahir MI,Rees NH,Heyes SJ,Cowley AR,Prout K

    更新日期:2008-07-01 00:00:00

  • Highly enantiomeric reduction of acetophenone and its derivatives by locally isolated Rhodotorula glutinis.

    abstract::Ninety isolates of microorganisms belonging to different taxonomical groups (30 bacteria, 20 yeast, and 40 fungi) were previously isolated from various samples. These isolates were screened as reducing agents for acetophenone 1a to phenylethanol 2a. It was found that the isolate EBK-10 was the most effective biocataly...


    pub_type: 杂志文章


    authors: Zilbeyaz K,Kurbanoglu EB

    更新日期:2010-10-01 00:00:00

  • Nonlinear chiral interactions in resolutions with benzylamine derivatives.

    abstract::N-formylphenylalanine was subjected to optical resolution using a chiral agent such as phenylethylamine enantiomer, (R)-phenylglycine methyl ester, (S)-N-benzyl-2-aminobutanol, alone or in a mixture with each other or in a mixture with benzylamine. ...


    pub_type: 杂志文章


    authors: Pálovics E,Fogassy E,Schindler J,Nógrádi M

    更新日期:2007-01-01 00:00:00