Strategic use of preparative chiral chromatography for the synthesis of a preclinical pharmaceutical candidate.

abstract：:The direct Michael addition reaction of cyclohexanone/aliphatic aldehydes with nitroolefins, catalyzed by a novel chiral pyrrolidine-thiourea catalyst 1a, is described. The desired 1,4-adducts were obtained in moderate yields with enantioselectivities up to 99% ee and dr up to 99:1 of the syn product. ...

journal_title：Chirality

authors： Shen Z,Zhang Y,Jiao C,Li B,Ding J,Zhang Y

更新日期：2007-05-05 00:00:00

abstract：:Perfluorooctane sulfonate (PFOS) is one of the most frequently detected perfluoroalkyl substances in environmental and human samples. Previous studies have shown that nonracemic PFOS in biological samples can be used as a marker of PFOS exposure sources. In recent years, supercritical fluid chromatography (SFC) has em...

journal_title：Chirality

authors： Zhao L,Chen F,Guo F,Liu W,Liu K

更新日期：2019-10-01 00:00:00

abstract：:Weinreb amide 3 was synthesized using isobutyl chloroformate, carbonyldiimidazole, or ethylcarbodiimide as the coupling agent in the reaction of Boc-phenylalanine with O,N-dimethylhydroxylamine hydrochloride. An optically active oil was isolated along with an optically inactive solid irrespective of the type of coupli...

journal_title：Chirality

authors： Zheng X,Donkor IO,Miller DD,Ross CR 2nd

更新日期：2000-01-01 00:00:00

abstract：:A rapid and simple procedure for enantioselective preparation of 2- and 3-substituted 2,3-dihydro[1,4]dioxino[2,3-b]pyridine derivatives (A and B, respectively) is described. The enantiomeric purity of each isomer was determined by capillary electrophoresis using a dual-cyclodextrin system (S-beta-CD/beta-CD) dissolve...

journal_title：Chirality

authors： Lazar S,Soukri M,El Haddad M,Akssira M,Leger JM,Jarry C,Morin P,Guillaumet G

更新日期：2005-01-01 00:00:00

abstract：:The R enantiomers of some of the 2-arylpropionic acid non-steroidal antiinflammatory drugs (NSAIDs) are known to undergo metabolic chiral inversion to their more pharmacologically active antipodes. This process is drug and species dependent and usually unidirectional. The S to R chiral inversion, on the other hand, is...

journal_title：Chirality

authors： Jamali F,Lovlin R,Aberg G

更新日期：1997-01-01 00:00:00

abstract：:A new colorimetric chiral sensor material consisting of three different functional sites such as chromophore (2,4-dinitrophenylazophenol dye), binding site (crown ether), and chiral barrier (3,3'-diphenyl-1,1'-binaphthyl group) was prepared and applied to the recognition of the two enantiomers of primary amino alcohol...

journal_title：Chirality

authors： Cho EN,Li Y,Kim HJ,Hyun MH

更新日期：2011-04-01 00:00:00

abstract：:The present study describes the development of two approaches for the determination of the enantiopurity of both enantiomers of indatraline. Initially, a method was developed using different chiral solvating agents (CSAs) for diastereomeric discrimination regarding signal separation in (1)H nuclear magnetic resonance ...

journal_title：Chirality

authors： Grimm SH,Allmendinger L,Höfner G,Wanner KT

更新日期：2013-12-01 00:00:00

abstract：:Caffeic acid-derived polyethers are a class of natural products isolated from the root extracts of comfrey and bugloss, which are endowed with intriguing pharmacological properties as anticancer agents. The synthesis of new polyether derivatives is achieved through ring-opening polymerization of chiral 2,3-disubstitut...

journal_title：Chirality

authors： Tedesco D,Fabini E,Barbakadze V,Merlani M,Zanasi R,Chankvetadze B,Bertucci C

更新日期：2015-12-01 00:00:00

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...

journal_title：Chirality

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

更新日期：1998-01-01 00:00:00

abstract：:The enantiomeric resolution of DL-alanine-DL-tryptophan dipeptide is described on amylose stationary phase. The eluent used was CH3 OH─CH3 COONH4 (10mM)─CH3 CN (50: 40, 10) at 0.8-mL/min flow, 230-nm detection, 25-minute run time, and 25°C ± 1°C temperature. The chiral phase was amylose [AmyCoat RP (15 cm × 0.46 cm × ...

journal_title：Chirality

authors： Ali I,Khattab RA,Alothman ZA,Badjah AY,Alwarthan A

更新日期：2018-04-01 00:00:00

abstract：:The stereochemistry of tolperisone, a chiral aryl-alkyl basic ketone was investigated by means of circular dichroism (CD) and ultraviolet (UV) spectroscopy. The unusually high optical activity of tolperisone hydrochloride in the n-->pi* region is interpreted by the presence of a chiral conformer in solution. For stere...

journal_title：Chirality

authors： Zsila F,Hollósi M,Gergely A

更新日期：2000-11-01 00:00:00

abstract：:Acyl glucuronides formed from carboxylic acids can undergo hydrolysis, acyl migration, and covalent binding to proteins. In buffers at physiological pH, the degradation of acylglucuronide of a chiral NSAID, carprofen, consisted mainly of acyl migration. Acidic pH reduced hydrolysis and acyl migration, thus stabilizing...

journal_title：Chirality

authors： Georges H,Presle N,Buronfosse T,Fournel-Gigleux S,Netter P,Magdalou J,Lapicque F

更新日期：2000-02-01 00:00:00

abstract：:To investigate the impacts of the widely used chiral herbicide fenoxaprop-ethyl (FE) on aquatic organisms, the enrichment, metabolism, acute toxicity, and oxidative stress of fenoxaprop-ethyl and its main metabolites fenoxaprop (FA), ethyl-2-(4-hydroxyphenoxy)propanoate (EHPP), 2-(4-hydroxyphenoxy)propanoic acid (HPPA...

journal_title：Chirality

authors： Xu Y,Jing X,Zhai W,Li X

更新日期：2020-07-01 00:00:00

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...

journal_title：Chirality

authors： Lao W,Gan J

更新日期：2012-01-01 00:00:00

abstract：:The optically active mixed-ligand fac(S)-tris(thiolato)rhodium(III) complexes, ΔL -fac(S)-[Rh(aet)2 (L-cys-N,S)](-) (aet = 2-aminoethanethiolate, L-cys = L-cysteinate) () and ΔLL -fac(S)-[Rh(aet)(L-cys-N,S)2 ](2-) were newly prepared by the equatorial preference of the carboxyl group in the coordinated L-cys ligand. T...

journal_title：Chirality

authors： Aizawa S,Tsubosaka S

更新日期：2016-01-01 00:00:00

abstract：:Ifosfamide (IF), a potent chemotherapeutic agent for solid tumors, is known to cause high rates of nephrotoxicity in children with cancer, which is most likely due to the renal production of the metabolite chloroacetaldehyde. Using plasma samples obtained from pediatric oncology patients, we developed a simple nonderi...

journal_title：Chirality

authors： Aleksa K,Nava-Ocampo A,Koren G

更新日期：2009-07-01 00:00:00

abstract：:Cyclodextrins that are indiscriminately carboxymethylated at the 2-, 3-, and 6-positions are used as chiral NMR solvating agents for cationic substrates with phenyl, naphthyl, pyridyl, indoline, and indole rings. Enantiodifferentiation with the alpha-, beta-, and gamma-cyclodextrin derivatives is compared. The carboxy...

journal_title：Chirality

authors： Provencher KA,Weber MA,Randall LA,Cunningham PR,Dignam CF,Wenzel TJ

更新日期：2010-03-01 00:00:00

abstract：:A method for the determination of (R)- and (S)-atenolol in human plasma and urine is described. The enantiomers of atenolol are extracted into dichloromethane containing 3% heptafluorobutanol followed by acetylation with acetic anhydride at 60 degrees C for 2 h. The acetylated enantiomers were separated on a chiral al...

journal_title：Chirality

authors： Enquist M,Hermansson J

更新日期：1989-01-01 00:00:00

abstract：:The chiral squaramide catalysts (8-15) were synthesized, and their catalytic efficiency in the enantioselective conjugate addition of pyrazolones to nitroalkenes was described. This protocol provides excellent chemical yields (up to 93%) of chiral 5-methyl-4-(2-nitro-1-arylethyl)pyrazol-3-ol derivatives with high enan...

journal_title：Chirality

authors： Aydin AE,Culha S

更新日期：2021-01-11 00:00:00

abstract：:Two new carotenoids, sapotexanthin 5,6-epoxide and sapotexanthin 5,8-epoxide, have been isolated from the ripe fruits of red mamey (Pouteria sapota). Sapotexanthin 5,6-epoxide was also prepared by partial synthesis via epoxidation of sapotexanthin, and the (5R,6S) and (5S,6R) stereoisomers were identified by high-perf...

journal_title：Chirality

authors： Murillo E,Agócs A,Nagy V,Király SB,Kurtán T,Toribio EM,Lakey-Beitia J,Deli J

更新日期：2020-05-01 00:00:00

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...

journal_title：Chirality

authors： Bednárová L,Malon P,Bour P

更新日期：2007-11-01 00:00:00

abstract：:The adsorption of heptahelicene, a helically shaped polyaromatic hydrocarbon (C(30)H(18)), on a Cu(111) surface was studied by means of thermal desorption mass spectrometry (TDMS) and low energy electron diffraction (LEED) at temperatures between 130-1,000 K under ultrahigh vacuum (UHV) conditions. The molecule in the...

journal_title：Chirality

authors： Ernst KH,Kuster Y,Fasel R,Müller M,Ellerbeck U

更新日期：2001-01-01 00:00:00

abstract：:In order to cope with the increasing number of publications on the separation of enantiomers by chromatography on a chiral stationary phase, the graphical molecular database CHIRBASE was created. In the present state, the database package covers information (structural, bibliographic, and chromatographic data) on liqu...

journal_title：Chirality

authors： Koppenhoefer B,Nothdurft A,Pierrot-Sanders J,Piras P,Popescu C,Roussel C,Stiebler M,Trettin U

更新日期：1993-01-01 00:00:00

abstract：:Herein, we present the solution-state NMR studies on dextromethorphan (1) under both isotropic and anisotropic conditions. From the measurement of 22 residual dipolar couplings using a stretched polystyrene gel (PS), we show that accurate and detailed structural information is readily determined including the relative...

journal_title：Chirality

authors： Swarbrick JD,Ashton TD

更新日期：2010-01-01 00:00:00

abstract：:Integrating spheres are widely used with UV-Vis and occasionally with infrared spectrophotometers to measure different types of samples, either in transmission mode (scattered transmission accessories) or in total/diffuse reflectance mode. We built a prototype sphere of the demountable type, which fits easily the samp...

journal_title：Chirality

authors： Castiglioni E,Albertini P

更新日期：2000-05-01 00:00:00

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 ...

journal_title：Chirality

authors： Wang M,Xie W,Li A,Xu S

更新日期：2016-10-01 00:00:00

abstract：:Novel chiral diisopropyl spiro bis(isoxazoline) ligands, anti-i-Pr-SPRIX and syn-i-Pr-SPRIX, were designed and synthesized. Their catalytic utility, X-ray crystallographic analyses, and complexation studies demonstrated the structural features of tetraisopropyl spiro bis(isoxazoline) ligand, i-Pr-SPRIX, which is a pro...

journal_title：Chirality

authors： Takenaka K,Lin X,Takizawa S,Sasai H

更新日期：2015-08-01 00:00:00

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....

journal_title：Chirality

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

更新日期：2009-01-01 00:00:00

abstract：:The impact of crystalline forces on the solid-state circular dichroism (CD) spectrum of hypothemycin (), a biologically active molecule extracted from natural sources, has been analyzed by means of time-dependent density functional theory CD calculations. Input structures were extracted from the X-ray geometry of and ...

journal_title：Chirality

authors： Pescitelli G

更新日期：2012-09-01 00:00:00

abstract：:Novel enantiopure 1,2,4-trizole-3-thiones containing a benzensulfonamide moiety were synthesized via multistep reaction sequence starting with D-phenylalanine methyl ester and L-phenylalanine ethyl ester as a source of chirality. The chemical structures of all compounds were characterized by elemental analysis, UV, IR...

journal_title：Chirality

authors： Başaran E,Karaküçük-Iyidoğan A,Schols D,Oruç-Emre EE

更新日期：2016-06-01 00:00:00