cas 93379-54-5, S(-)-ATENOLOL | Articles data

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Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC
A triazole-bridged bis(β-cyclodextrin) was synthesized via a high-yield Click Chemistry reaction between 6-azido-β-cyclodextrin and 6-propynylamino-β-cyclodextrin, and then it was bonded onto ordered silica gel SBA-15 to obtain a novel triazole-bridged bis (β-cyclodextrin)–bonded chiral stationary phase (TBCDP). The structures of the bridged cyclodextrin and TBCDP were characterized by the infrared spectroscopy, mass spectrometry, elemental analysis, and thermogravimetric analysis. The chiral performance of TBCDP was evaluated by using chiral pesticides and drugs as probes including triazoles, flavanones, dansyl amino acids and β-blockers. Some effects of the composition in mobile phase and pH value on the enantioseparations were investigated in different modes. The nine triazoles, eight flavanones, and eight dansyl amino acids were successfully resolved on TBCDP under the reversed phase with the resolutions of hexaconazole, 2′-hydroxyflavanone, and dansyl-DL-tyrosine, which were 2.49, 5.40, and 3.25 within 30 minutes, respectively. The ten β-blockers were also separated under the polar organic mode with the resolution of arotinolol reached 1.71. Some related separation mechanisms were discussed preliminary. Compared with the native cyclodextrin stationary phase (CDSP), TBCDP has higher enantioselectivity to separate more analytes, which benefited from the synergistic inclusion ability of the two adjacent cavities and bridging linker of TBCDP, thereby enabling it a promising prospect in chiral drugs and food analysis.
Shuang, Yazhou,Liao, Yuqin,Wang, Hui,Wang, Yuanxing,Li, Laisheng
p. 168 - 184
(2019/11/25)

Enantioseparation of chiral pharmaceuticals by vancomycin-bonded stationary phase and analysis of chiral recognition mechanism
The drug chirality is attracting increasing attention because of different biological activities, metabolic pathways, and toxicities of chiral enantiomers. The chiral separation has been a great challenge. Optimized high-performance liquid chromatography (HPLC) methods based on vancomycin chiral stationary phase (CSP) were developed for the enantioseparation of propranolol, atenolol, metoprolol, venlafaxine, fluoxetine, and amlodipine. The retention and enantioseparation properties of these analytes were investigated in the variety of mobile phase additives, flow rate, and column temperature. As a result, the optimal chromatographic condition was achieved using methanol as a main mobile phase with triethylamine (TEA) and glacial acetic acid (HOAc) added as modifiers in a volume ratio of 0.01% at a flow rate of 0.3?mL/minute and at a column temperature of 5°C. The thermodynamic parameters (eg, ΔH, ΔΔH, and ΔΔS) from linear van 't Hoff plots revealed that the retention of investigated pharmaceuticals on vancomycin CSP was an exothermic process. The nonlinear behavior of lnk′ against 1/T for propranolol, atenolol, and metoprolol suggested the presence of multiple binding mechanisms for these analytes on CSP with variation of temperature. The simulated interaction processes between vancomycin and pharmaceutical enantiomers using molecular docking technique and binding energy calculations indicated that the calculated magnitudes of steady combination energy (ΔG) coincided with experimental elution order for most of these enantiomers.
Li, Jiaxi,Liu, Ruixia,Wang, Liyang,Liu, Xiaoling,Gao, Hongjie
p. 236 - 247
(2019/02/01)

Preparation and characterization of a new open-tubular capillary column for enantioseparation by capillary electrochromatography
In order to use the enantioseparation capability of cationic cyclodextrin and to combine the advantages of capillary electrochromatography (CEC) with open-tubular (OT) column, in this study, a new OT-CEC, coated with cationic cyclodextrin (1-allylimidazolium-β-cyclodextrin [AI-β-CD]) as chiral stationary phase (CSP), was prepared and applied for enantioseparation. Synthesized AI-β-CD was characterized by infrared (IR) spectrometry and mass spectrometry (MS). The preparation conditions for the AI-β-CD-coated column were optimized with the orthogonal experiment design L9(34). The column prepared was characterized by scanning electron microscopy (SEM) and elemental analysis (EA). The results showed that the thickness of stationary phase in the inner surface of the AI-β-CD-coated columns was about 0.2 to 0.5?μm. The AI-β-CD content in stationary phase based on the EA was approximately 2.77?mmol·m?2. The AI-β-CD-coated columns could separate all 14 chiral compounds (histidine, lysine, arginine, glutamate, aspartic acid, cysteine, serine, valine, isoleucine, phenylalanine, salbutamol, atenolol, ibuprofen, and napropamide) successfully in the study and exhibit excellent reproducibility and stability. We propose that the column, coated with AI-β-CD, has a great potential for enantioseparation in OT-CEC.
Li, Yingjie,Tang, Yimin,Qin, Shili,Li, Xue,Dai, Qiang,Gao, Lidi
p. 283 - 292
(2019/02/05)

Factors screening to statistical experimental design of racemic atenolol kinetic resolution via transesterification reaction in organic solvent using free Pseudomonas fluorescens lipase
As the (R)-enantiomer of racemic atenolol has no β-blocking activity and no lack of side effects, switching from the racemate to the (S)-atenolol is more favorable. Transesterification of racemic atenolol using free enzymes investigated as a resource to resolve the racemate via this method is limited. Screenings of enzyme, medium, and acetyl donor were conducted first to give Pseudomonas fluorescens lipase, tetrahydrofuran, and vinyl acetate. A statistical design of the experiment was then developed using Central Composite Design on some operational factors, which resulted in the conversions of 11.70–61.91% and substrate enantiomeric excess (ee) of 7.31–100%. The quadratic models are acceptable with R2 of 95.13% (conversion) and 89.63% (ee). The predicted values match the observed values reasonably well. Temperature, agitation speed, and substrate molar ratio factor have low effects on conversion and ee, but enzyme loading affects the responses highly. The interaction of temperature–agitation speed and temperature–substrate molar ratio show significant effects on conversion, while temperature–agitation speed, temperature–substrate molar ratio, and agitation speed–substrate molar ratio affect ee highly. Optimum conditions for the use of Pseudomonas fluorescens lipase, tetrahydrofuran, and vinyl acetate were found at 45°C, 175?rpm, 2000?U, and 1:3.6 substrate molar ratio.
Agustian, Joni,Kamaruddin, Azlina Harun,Aboul-Enein, Hassan Y.
p. 376 - 385
(2017/06/19)

Enantioseparation of (RS)-atenolol with the use of lipases immobilized onto new-synthesized magnetic nanoparticles
The enzymatic method was used for the direct resolution of racemic atenolol. The catalytic activities of commercially available lipases from Candida rugosa (MY and OF) immobilized onto new-synthesized chitosan magnetic nanoparticles [Fe3O4-CS-Et(NH2)2, Fe3O4-CS-Et(NH2)3] in the kinetic resolution of racemic atenolol were compared. The best results were obtained by using Candida rugosa lipase OF immobilized onto Fe3O4-CS-Et(NH2)3. Additionally, the enzyme reusability was investigated. It was established that even after 5 reaction cycles, both lipases from Candida rugosa maintained their high catalytic activities and operational stabilities. This approach is extremely important from an economical point of view, because it allows for a direct cost reduction of the biotransformation.
Sikora, Adam,Che?miniak-Dudkiewicz, Dorota,Ziegler-Borowska, Marta,Marsza??, Micha? Piotr
p. 374 - 380
(2017/02/18)

Enantioselective potential of polysaccharide-based chiral stationary phases in supercritical fluid chromatography
The enantioselective potential of two polysaccharide-based chiral stationary phases for analysis of chiral structurally diverse biologically active compounds was evaluated in supercritical fluid chromatography using a set of 52 analytes. The chiral selectors immobilized on 2.5?μm silica particles were tris-(3,5-dimethylphenylcarmabate) derivatives of cellulose or amylose. The influence of the polysaccharide backbone, different organic modifiers, and different mobile phase additives on retention and enantioseparation was monitored. Conditions for fast baseline enantioseparation were found for the majority of the compounds. The success rate of baseline and partial enantioseparation with cellulose-based chiral stationary phase was 51.9% and 15.4%, respectively. Using amylose-based chiral stationary phase we obtained 76.9% of baseline enantioseparations and 9.6% of partial enantioseparations of the tested compounds. The best results on cellulose-based chiral stationary phase were achieved particularly with propane-2-ol and a mixture of isopropylamine and trifluoroacetic acid as organic modifier and additive to CO2, respectively. Methanol and basic additive isopropylamine were preferred on amylose-based chiral stationary phase. The complementary enantioselectivity of the cellulose- and amylose-based chiral stationary phases allows separation of the majority of the tested structurally different compounds. Separation systems were found to be directly applicable for analyses of biologically active compounds of interest.
Kucerova, Gabriela,Kalikova, Kveta,Tesarova, Eva
supporting information
p. 239 - 246
(2017/05/29)

Enantio-conversion and -selectivity of racemic atenolol kinetic resolution using free Pseudomonas fluorescens lipase (Amano) conducted via transesterification reaction
In this report, effects of reaction parameters on kinetic resolution of racemic atenolol using Pseudomonas fluorescens lipase were investigated via transesterification for production of pharmacologically active eutomer (S)-atenolol with high enantiomeric purity. It was found that a temperature of 45 °C produced an acceptable enantioselectivity (E: 17). Good agitation speeds were found at 170-230 rpm producing E values of 12-15, whilst an enzyme activity of ≥2500 U gave 100% conversion of the (S)-atenolol. Substrate concentrations of 11.26-18.80 mM gave E values of 11.6-12.3. Variation of the substrate molar ratio yielded (S)-atenolol conversions of 44.67-61.58% with E = 12-23.
Agustian, Joni,Kamaruddin, Azlina Harun,Aboul-Enein, Hassan Y.
p. 26077 - 26085
(2016/03/25)

The Reaction Mechanism and Kinetics Data of Racemic Atenolol Kinetic Resolution via Enzymatic Transesterification Process Using Free Pseudomonas fluorescence Lipase
A thorough study on free-enzyme transesterification kinetic resolution of racemic atenolol in a batch system was investigated to gain knowledge for (S)-atenolol kinetics. Analyses of enzyme kinetics using Sigma-Plot 11 Enzyme Kinetics Module on the process are based-on Michaelis-Menten and Lineweaver-Burk plot, which give first-order reaction and ordered-sequential Bi-Bi mechanism, where Vmax, KM-vinyl acetate, and KM-(S)-atenolol are 0.80 mM/h, 29.22 mM, and 25.42 mM, respectively. Further analyses on enzyme inhibitions find that both substrates inhibit the process where (S)-atenolol and vinyl acetate develop competitive inhibition and mixed inhibition, respectively. Association of (S)-atenolol with free enzyme to inhibit the enzyme is higher than reaction of active enzyme-substrate complex with vinyl acetate.
Agustian, Joni,Harun Kamaruddin, Azlina
p. 253 - 265
(2016/04/06)

Lipase-catalyzed green synthesis of enantiopure atenolol
A new green route is proposed for the synthesis of enantiopure atenolol (a β1-blocker). An enzymatic kinetic resolution approach was used to synthesize the enantiopure intermediates (R)- and (S)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetamide from the corresponding racemic alcohol. Of the commercially available lipases screened, Candida antarctica lipase-A (CLEA) showed maximum enantioselectivity in the transesterification of the racemic alcohol using vinyl acetate as the acyl donor. The reactions afforded the (S)-alcohol along with the (R)-acetate, with 48.9% conversion (E = 210, eeP = 96.9% and eeS = 91.1%). Various reaction parameters were optimized in order to achieve maximum enantioselectivity. N-alkylation of the (S)-alcohol with isopropylamine afforded the (S)-atenolol, and the (R)-acetate was chemically hydrolyzed to the corresponding alcohol and further converted to the (R)-atenolol via N-alkylation of the (R)-alcohol with isopropylamine. The use of ionic liquids, to solve the solubility related problems of the drug intermediates, made this process greener and more efficient compared to the previously reported methods. This journal is
Dwivedee, Bharat Prasad,Ghosh, Saptarshi,Bhaumik, Jayeeta,Banoth, Linga,Chand Banerjee, Uttam
p. 15850 - 15860
(2015/03/04)

Effect of basic and acidic additives on the separation of some basic drug enantiomers on polysaccharide-based chiral columns with acetonitrile as mobile phase
The separation of enantiomers of 16 basic drugs was studied using polysaccharide-based chiral selectors and acetonitrile as mobile phase with emphasis on the role of basic and acidic additives on the separation and elution order of enantiomers. Out of the studied chiral selectors, amylose phenylcarbamate-based ones more often showed a chiral recognition ability compared to cellulose phenylcarbamate derivatives. An interesting effect was observed with formic acid as additive on enantiomer resolution and enantiomer elution order for some basic drugs. Thus, for instance, the enantioseparation of several β-blockers (atenolol, sotalol, toliprolol) improved not only by the addition of a more conventional basic additive to the mobile phase, but also by the addition of an acidic additive. Moreover, an opposite elution order of enantiomers was observed depending on the nature of the additive (basic or acidic) in the mobile phase.
Gogaladze, Khatuna,Chankvetadze, Lali,Tsintsadze, Maia,Farkas, Tivadar,Chankvetadze, Bezhan
p. 228 - 234
(2015/03/18)

Chiral separations of some β-adrenergic agonists and antagonists on AmyCoat column by HPLC
Sixteen β-adrenergic antagonists namely acebutalol, alprenolol, atenolol, bisoprolol, bopindolol, bufurolol, carazolol, celiprolol, indenolol, metaprolol, nebivolol, oxprenolol, practolol, propranolol, tertalol, and timolol, and two β-adrenergic agonists namely cimeterol and clenbuterol were resolved on AmyCoat (150 x 46 mm, 3 μm size of silica particle) by using (85:15:0.1, v/v/v), (90:10:0.1, v/v/v), and (95:05:0.1, v/v/v) combinations of η-heptane, ethanol, and diethylamine solvents, respectively. The flow rates used were 0.5, 1.0, 2.0, and 3.0 ml/min with detection at 225 nm. The values of capacity, separation, and resolution factors ranged from 0.38 to 19.70, 1.08-2.33, and 1.0 and 4.50, respectively. The maximum and minimum resolutions were achieved for celiprolol and bufurolol, respectively. The chiral recognition mechanisms were also discussed. The values of validation parameters were calculated.
Ali, Imran,Saleem, Kishwar,Gaitonde, Vinay D.,Aboul-Enein, Hassan Y.,Hussain, Iqbal
experimental part
p. 24 - 28
(2010/09/14)

Enantioselective synthesis of β-blockers via hydrolytic kinetic resolution of terminal oxiranes by using bimetallic chiral {{2,2′- [cyclohexane-1,2-diylbis(nitrilomethylidyne)]bis[phenolato]}(2-)}cobalt ([Co(salen)])-type complexes
The synthesis of chirally pure β-blockers was successfully achieved via hydrolytic kinetic resolution of butyl (±)-4-(oxiran-2-ylmethoxy) benzeneacetate ((±)-1) and (±)-4-(oxiran-2-ylmethoxy) benzeneacetonitrile ((±)-2) in the presence of bimetallic chiral [Co(salen)]-type complexes. The newly synthesized bimetallic chiral [Co(salen)]-type complexes exhibited excellent enantioselectivities of up to >98% ee in good yields (Tables 1-3).
Kawthekar, Rahul B.,Kim, Geon-Joong
scheme or table
p. 317 - 332
(2009/02/07)

Process for producing atenolol of high optical purity
The present invention relates to an improved process for producing optically active (S)-atenolol of formula (1) in high optical purity by reacting a phenol with an epichlorohydrin.
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(2008/06/13)

NOVEL DIASTERIOMERIC SALTS OF ATENOLOL AND THEIR USE IN THE PRODUCTION OF OPTICALLY ACTIVE ATENOLOL
Novel diasteriomeric tartaric acid salts of atenolol namely, (2S)-1-isopropylamino-3-[4-(2-acetamido)phenoxy]-2-propanol-(2S,3S)-O,O-di-p-toluoyltartrate, (2R)-1-isopropylamino-3-[p-(2-methoxyethyl)phenoxy]-2-propanol-(2R,3R)-O,O-di-p-toluoyltartrate and their use in the preparation of optically active atenolol by a simple industrial racemic resolution is disclosed herein.
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(2008/06/13)

An efficient asymmetric synthesis of (S)-atenolol: Using hydrolytic kinetic resolution
Enantiomerically pure (S)-atenolol was prepared by using (R,R) salen Co(III) complex for the resolution of terminal epoxide. This process was carried out at room temperature in excellent enantio selectivity. The method can be applied for large-scale preparation of (S)-atenolol without any problem.
Subhas Bose,Venkat Narsaiah
p. 627 - 630
(2007/10/03)

Process for the preparation of 3-amino-2-hydroxy-1-propyl ethers
PCT No. PCT/JP97/03220 Sec. 371 Date Apr. 28, 1999 Sec. 102(e) Date Apr. 28, 1999 PCT Filed Sep. 12, 1997 PCT Pub. No. WO98/12171 PCT Pub. Date Mar. 26, 1998A process for preparation of 3-amino-2-hydroxy-1-propyl ether of the formula wherein R1 is substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic ring, R2 and R3 are the same or different hydrogen atom, a substituted or unsubstituted alkyl, or may form a ring together with an adjacent nitrogen atom, which ring may be interrupted with nitrogen atom, oxygen atom or sulfur atom, which is characterized in reacting an epoxy compound of the formula wherein X is halogen, in the presence of a fluoride salt, with an alcohol and then reacting an amine. According to the above method, an intermediates for synthesis of medicines is obtained in good yield and highly optical purity.
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(2008/06/13)

Biotransformations with Rhizopus arrhizus and Geotrichum candidum for the preparation of (S)-atenolol and (S)-propranolol
(±)-Atenolol/(±)-propranolol and their acetates were incubated with the fungus Rhizopus arrhizus and Geotrichum candidum separately for different time intervals to afford (S)-atenolol/(S)-propranolol in good optical yield. The time and pH for this biotransformation was optimised. The present biodegradations using Rhizopus arrhizus and Geotrichum candidum provides a simple and useful method to obtain (S)-atenolol and (S)-propranolol which are active enantiomers of the β-adrenergic blockers. Copyright (C) 2000 Elsevier Science Ltd.
Damle, Subhash V.,Patil, Prashant N.,Salunkhe, Manikrao M.
p. 2067 - 2070
(2007/10/03)

One pot synthesis of (±)/(S)-atenolol and (±)/(S)-propranolol by employing polymer supported reagent
(±)/(S)-Atenolol and (±)/(S)-propranolol were synthesized by using reaction of (±)/(S)-epichlorohydrin with polymer supported phenoxide anion followed by reaction with isopropylamine.
Damle, Subhash V.,Patil, Prashant N.,Salunkhe, Manikrao M.
p. 1639 - 1644
(2007/10/03)

Chemoenzymatic synthesis of (R)- and (S)-atenolol and propranolol employing lipase catalyzed enantioselective esterification and hydrolysis
Chemoenzymatic synthesis of (R) - and (S) - atenolol and propranolol employing lipase catalyzed enantioselective esterification and hydrolysis is described.
Damle, Subhash V.,Patil, Prashant N.,Salunkhe, Manikrao M.
p. 3855 - 3862
(2007/10/03)

CsF in organic synthesis. Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure β-blockers
The two modes of the paths in the reaction of oxiranes with phenols are completely controlled by CsF. Glycidyl nosylate undergoes exclusive substitution at the C1 position whereas the ring-opening (C-3 attack) occurs with epichlorohydrin, glycidol, and 1,2-epoxyalkanes. These reactions provide convenient access to enantiopure β-blockers.
Kitaori, Kazuhiro,Furukawa, Yoshiro,Yoshimoto, Hiroshi,Otera, Junzo
p. 14381 - 14390
(2007/10/03)

Convenient preparation of enantiopure atenolol by means of preferential crystallization
(R)- or (S)-Atenolol (1) in enantiopure form was prepared in an extremely simple way. Atenolol of ca. 95% ee was prepared in one-pot from p- hydroxyphenylacetamide (2) and (R)- or (S)-epichlorohydrin (3). Then, preferential crystallization of the Brensted's acid salts of the resulting atenolol improved the enantiomeric purity up to 99.8% ee.
Kitaori, Kazuhiro,Takehira, Yosikazu,Furukawa, Yoshiro,Yoshimoto, Hiroshi,Otera, Junzo
p. 505 - 507
(2007/10/03)

A practical synthesis of optically active atenolol from chiral epichlorohydrin
The synthesis of (R)- and (S)-atenolol (1) was achieved in two steps starting from p-hydroxyphenylacetamide (2). Both enantiomers of the glycidyl ether 4 were synthesized from 2 and (R)- and (S)-epichlorohydrin (3) using an alkali metal hydroxide and/or BTA (benzyltrimethylammonium chloride), respectively. Subsequent treatment of 4 with isopropylamine afforded atenolol (1) with excellent enantiomeric excess (> 98% ee).
Kitaori, Kazuhiro,Takehira, Yoshikazu,Furukawa, Yoshiro,Yoshimoto, Hiroshi,Otera, Junzo
p. 412 - 414
(2007/10/03)

Process of preparing enriched enantiomers of glycerol carbonate and derivatives thereof for synthesis of β-blockers
Enriched enantiomers of glycerol Carbonate are produced under the influence of a hydrolytic enzyme, either by selective esterification of racemic glycerol carbonate or by selective hydrolysis of an ester of the racemate. The enriched enantiomeric product is readily converted to starting materials and intermediates useful in the synthesis of enantiomerically pure therapeutic agents, such as β-adrenergic blockers.
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(2008/06/13)

Lipase catalysis in organic solvents. Application to the synthesis of (R)- and (S)-atenolol
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Bevinakatti,Banerji
p. 6003 - 6005
(2007/10/02)

Process for producing optically active atenolol and intermediate thereof
Improved process for producing an optically active atenolol useful as a β-adrenergic blocker for the treatment of angina pectoris, arrhythmia and hypertension, which comprising reacting a phenol compound with an optically active epihalohydrin to give an intermediate, optically active glycidyl ether compound, followed by reacting the intermediate with isopropylamine, and purification method of the optically active atenolol in high yield by means of forming a salt of atenolol with a Bronsted's acid whereby the salt of optically active atenolol having high optical purity can be separated from the salt of racemic atenolol by solid-liquid separation method.
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(2008/06/13)

Process for the preparation of esters of 4-(2,3-epoxypropoxy)phenylacetic acid and 4-(2-hydroxy-3-isopropylamino-propoxy)phenylacetic acid and/or atenolol in stereospecific form
S-(-)-atenolol (4-(2-hydroxy-3-isopropylaminopropoxy)phenyl acetamide) is obtained by a process including the step of stereo-specific epoxidation by an ester of 4-allyloxyphenyl-acetic acid using a micro-organism capable of stereo-selective epoxidation, e.g. Pseudomonasoleovorans, to produce the corresponding ester of 4-(2,3-epoxypropoxy)phenylacetic acid which is predominantly in S configuration. PseudomonasoleovoransATCC 29347 produces at least about 90% of the epoxypropoxy compound in Sconfiguration. The resulting epoxypropoxy compound can be converted into atenolol, maintaining the high proportion of Sconfiguration, by reacting the epoxypropoxy compound with isopropylamine and converting the ester group to an amide group by reaction with ammonia.
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(2008/06/13)