Excavations in drug chirality: 1. Cyclothiazide.

abstract：:Resolution of mandelic acid with (-)-(1R,2S)-ephedrine in water and ethanol produces intermediate diastereomeric salts with greatly disparate solubilities and melting points. Single crystal X-ray analysis of the less (L) and more (M) soluble (-)-ephedrinium mandelates (I, II) shows crystal structures which are isoster...

journal_title：Chirality

authors： Valente EJ,Zubkowski J,Eggleston DS

更新日期：1992-01-01 00:00:00

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...

journal_title：Chirality

authors： Borkin DA,Landge SM,Török B

更新日期：2011-09-01 00:00:00

abstract：:Racemic ketoconazole (KTZ) was the first orally active azole antifungal agent used in clinical practice and has become widely used in the treatment of mucosal fungal infections associated with AIDS immunosuppression and cancer chemotherapy. However, the use of KTZ has been limited because of adverse drug-drug interact...

journal_title：Chirality

authors： Dilmaghanian S,Gerber JG,Filler SG,Sanchez A,Gal J

更新日期：2004-02-01 00:00:00

abstract：:The electronic circular dichroism (ECD) spectra of two sesquiterpenoids (1 and 2) related to oplopanone, obtained from a methanolic extract of the plant Serphidium stenocephalum (Artemisia stenocephala), were measured and reproduced by means of time-dependent density functional theory (TDDFT) calculations, establishin...

journal_title：Chirality

authors： Shafiq N,Saleem M,Riaz N,Tousif MI,Jabbar A,Tareen RB,Pescitelli G

更新日期：2014-01-01 00:00:00

abstract：:Chiral pesticides currently constitute about 50% of all pesticides dosage used in China, and this ratio is increasing as more complex structures are introduced. Dichlorprop methyl (DCPPM) is a chiral herbicide consisting of a pair of enantiomers. In this study, the enantiomeric separation of DCPPM was investigated by ...

journal_title：Chirality

authors： Ma Y,Xu C,Wen Y,Liu W

更新日期：2009-04-01 00:00:00

abstract：:A systematic and comprehensive study of the conformational spaces of the Cinchona alkaloids quinine, quinidine, cinchonine, cinchonidine, epiquinine, epiquinidine, epicinchonine, and epicinchonidine using the semiempirical PM3 method is described. The results were analyzed in terms of syn/anti and open/closed/hindered...

journal_title：Chirality

authors： Caner H,Biedermann PU,Agranat I

更新日期：2003-08-01 00:00:00

abstract：:Planar 2(5H)-furanones substituted at C4 with a chiral pyrrolidinyl group show CD spectra which are apparently due to the distortion of the C4-N1 bond of sp2 character from the plane defined by the 2(5H)-furanone ring atoms and/or due to the presence of substituents in the pyrrolidine ring. This is a new, previously n...

journal_title：Chirality

authors： Gawroński J,Gawrońska K,Kwit M,Kacprzak K,Rychlewska U

更新日期：2004-08-01 00:00:00

abstract：:A method is described for the HPLC analysis of oxamniquine enantiomers in liver fraction incubates, using a second-generation alpha 1-acid glycoprotein-based column (Chiral-AGP). Oxamniquine is extracted from the incubation media by liquid-liquid extraction, using diethyl ether. The dried residue is redissolved in elu...

journal_title：Chirality

authors： Noctor TA,Fell AF,Kaye B

更新日期：1990-01-01 00:00:00

abstract：:Three β-keto sulfoxides (1-3) were synthesized in enantiopure form and investigated by means of circular dichroism (CD) spectroscopy, both in electronic and vibrational range (ECD, VCD), in combination with quantum chemical calculations. For compound 2, the X-ray structure was available; thus, the ECD in the solid sta...

journal_title：Chirality

authors： Górecki M,Capozzi MAM,Albano G,Cardellicchio C,Di Bari L,Pescitelli G

更新日期：2018-01-01 00:00:00

abstract：:Kinetic and equilibrium binding studies were performed on the interaction of warfarin enantiomers with human serum albumin (HSA) in the absence and presence of lorazepam acetate (LoAc) enantiomers. Binding kinetics were followed by recording changes in the fluorescence of warfarin upon binding to HSA using the stopped...

journal_title：Chirality

authors： Fitos I,Visy J,Kardos J

更新日期：2002-05-15 00:00:00

abstract：:Both epimers of the naturally occurring nonproteinogenic amino acid L-cyclopentenylglycine, (2S,1'S)- and (2S, 1'R)-2-(cyclopent-2'-enyl)glycine, were obtained via a procedure involving condensation of 3-chlorocyclopentene with diethyl acetylaminomalonate, deethoxycarbonylation, chromatographic separation of the resul...

journal_title：Chirality

authors： Andersen L,Nielsen B,Jaroszewski JW

更新日期：2000-10-01 00:00:00

abstract：:4-l-menthyloxycarbonyl 5-aryl prolinates were studied as organocatalysts of a novel three-component reaction of cyclohexanone, benzoic acid, and β-nitrostyrene. The presence of ortho-halogen atom in 5-aryl fragment of the catalyst is favored for driving the formation of chiral 7a-hydroxyoctahydro-2H-indol-2-one scaffo...

journal_title：Chirality

authors： Ivantcova PM,Kudryavtsev KV

更新日期：2020-06-01 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：:The five-steps synthesis of a hemicryptophane cage combining a benzene-1,3,5-tricarboxamide unit and a cyclotriveratrylene (CTV) moiety is described. Chiral high-performance liquid chromatography (HPLC) was used to resolve the racemic mixture. The absolute configuration of the isolated enantiomers was assigned by comp...

journal_title：Chirality

authors： Long A,Jean M,Albalat M,Vanthuyne N,Giorgi M,Górecki M,Dutasta JP,Martinez A

更新日期：2019-11-01 00:00:00

abstract：:The perturbation of the racemic equilibrium of luminescent D3 terbium(III) complexes with chelidamic acid (CDA), a hydroxylated derivative of 2,6-pyridine-dicarboxylic acid (DPA), by added chiral biomolecules such as L-amino acids has been studied using circularly polarized luminescence and 13C NMR spectroscopy. It is...

journal_title：Chirality

authors： Moussa A,Pham C,Bommireddy S,Muller G

更新日期：2009-05-01 00:00:00

abstract：:Isophthalic and terephthalic acid monoesters of cyclic nigerosyl-(1→6)-nigerose (CNN), a cyclic tetrasaccharide composed of four d-glucopyranosyl residues connected by alternating α-1,3- and α-1,6-linkages, were synthesized as novel chiral supramolecular sensitizers for enantiodifferentiating photoisomerization of (Z)...

journal_title：Chirality

authors： Yang C,Liang W,Nishijima M,Fukuhara G,Mori T,Hiramatsu H,Dan-oh Y,Tsujimoto K,Inoue Y

更新日期：2012-11-01 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 rapid and effective RP-UHPLC-DAD method for enantioseparation of three flavanones, i.e., flavanone, naringenin, and hesperetin, was developed and validated. Chromatographic separation of the analytes was performed using a Chiralpak AD-3R analytical column under reverse phase conditions with methanol as the mobile ph...

journal_title：Chirality

authors： Baranowska I,Hejniak J,Magiera S

更新日期：2016-02-01 00:00:00

abstract：:Subcellular fractions of three human brain specimens were found to contain esterase activities which hydrolyzed racemic oxazepam 3-acetate (rac-OXA). All three human brain preparations were highly selective toward the S-enantiomer of rac-OXA. ...

journal_title：Chirality

authors： Yang SK,Huang A,Huang JD

更新日期：1993-01-01 00:00:00

abstract：:The known complex trans-RuCl2(NBD)Py2 (1, NBD is norbornadiene, Py is pyridine) reacts with either (R)-BINAP ((R)-2, 2'-bis(diphenylphosphino)-1,1'-binaphthyl), (S;S)-Chiraphos ((2S;3S-(-)-2,3-bis(diphenylphosphino)butane), (S;S)-Skewphos ((2S;4S)-(-)-2,4-bis(diphenylphosphino)pentane), (R)-(S)-Josiphos ((R)-(-)-1-[(S...

journal_title：Chirality

authors： Akotsi OM,Metera K,Reid RD,McDonald R,Bergens SH

更新日期：2000-06-01 00:00:00

abstract：:Chiral Eu3+ -based systems are frequently studied via circularly polarized luminescence spectroscopy. The emission lifetimes of each circular polarization, however, are virtually always ignored, because in a homogeneous sample of emitters, there should be no difference between the two. However, we show that in less ro...

journal_title：Chirality

authors： Hananel U,Schwartz G,Paiss G,Arrico L,Zinna F,Di Bari L,Cheshnovsky O,Markovich G

更新日期：2020-12-30 00:00:00

abstract：:The application of the Cartesian coordinate tensor transfer (CCT) technique for simulations of the IR absorption and vibrational circular dichroism (VCD) spectra of relatively large nucleic acid fragments is demonstrated on several case studies. The approach is based on direct ab initio calculations of atomic tensors,...

journal_title：Chirality

authors： Andrushchenko V,Bouř P

更新日期：2010-01-01 00:00:00

abstract：:C(25) highly branched isoprenoid (HBI) alkenes are ubiquitous lipids found in geochemical samples around the globe. The origins of these widespread geochemicals are believed to be restricted to a limited number of diatoms, including Haslea ostrearia (and related species), Rhizosolenia setigera, and Pleurosigma interme...

journal_title：Chirality

authors： Belt ST,Allard WG,Johns L,König WA,Massé G,Robert JM,Rowland S

更新日期：2001-08-01 00:00:00

abstract：:Here, we report the general strategies by which NMR spectroscopy can be used to determine the enantiopurity and absolute configuration of chalcogen containing secondary alcohols, including the evaluation of the use of chiral solvating and chiral derivatizing agents. The BINOL/DMAP ternary complex demonstrated a simple...

journal_title：Chirality

authors： Marques NBG,Jacob RG,Perin G,Lenardão EJ,Alves D,Silva MS

更新日期：2019-01-01 00:00:00

abstract：:[3β,5β,7α,12α]-3-(4-t-Butylbenzoilamine)-7,12-dihydroxycholan-24-oic acid was synthesized and recrystallized from chlorobenzene and acetone. Orthorhombic P2(1)2(1)2(1) and monoclinic P2(1) crystals were obtained, respectively, and both crystals include solvent and water molecules with a 1:1:1 stoichiometry. In the sec...

journal_title：Chirality

authors： Meijide F,Trillo JV,Soto VH,Jover A,Tato JV

更新日期：2011-11-01 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：: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：:(S)-(-)-2-(α-hydroxyethyl)-benzimidazole and (S)-(+)-2-(α-hydroxybenzyl)-benzimidazole work as chiral Brønsted bases (BBs) in Diels-Alder reaction between anthrone and maleimides under mild reaction condition. These chiral BBs cause asymmetric induction. ...

journal_title：Chirality

authors： Mirgane NA,Karnik AV

更新日期：2011-05-01 00:00:00

abstract：:Benalaxyl (BX), methyl-N-phenylacetyl-N-2,6-xylyl alaninate, is a potent acylanilide fungicide and consist of a pair of enantiomers. The stereoselective metabolism of BX was investigated in rat and rabbit microsomes in vitro. The degradation kinetics and the enantiomer fraction (EF) were determined using normal high-p...

journal_title：Chirality

authors： Zhang P,Zhu W,Dang Z,Shen Z,Xu X,Huang L,Zhou Z

更新日期：2011-02-01 00:00:00

abstract：:In the past years, enantioanalysis became very important for clinical analysis; biomarkers/substances of biomedical importance with chiral structure should be analyzed and their presence correlated with the specific disorder. Therefore, we developed a method for the assay of l- and d-glucose, based on molecular recogn...

journal_title：Chirality

authors： Stefan-van Staden RI,Mitrofan G

更新日期：2018-05-01 00:00:00