PL EN


Preferences help
enabled [disable] Abstract
Number of results
Journal
2014 | 1 | 1 |
Article title

Biocatalytic synthesis of (S)-Practolol, a selective
β-blocker

Content
Title variants
Languages of publication
EN
Abstracts
EN
The present study describes an efficient
chemoenzymatic synthesis of enantiopure (S)-Practolol,
a selective β-adrenergic receptor blocker. Prior to
the synthesis of the target, a synthetic protocol for
(RS)-N-4-(3-chloro-2-hydroxypropoxy)phenylacetamide,
an essential precursor, was developed. Various commercial
lipases were screened for the kinetic resolution of (RS)-
N-4-(3-chloro-2-hydroxypropoxy)phenylacetamide using
toluene as solvent and vinyl acetate as an acyl donor.
Among various lipases screened, Pseudomonas cepacia
sol-gel AK showed the highest enantioselectivity (96%
enantiomeric excess with 50% conversion), affording
(S)-1-(4-acetamidophenoxy)-3-chloropropan-2-yl acetate.
Optimization of the reaction parameters was carried
out in order to find the best-suited conditions for the
biocatalysis. Furthermore, the enantiopure intermediate
was hydrolyzed and the resulting product was reacted with
isopropylamine to afford (S)-Practolol. This biocatalytic
procedure depicts a green technology for the synthesis of
(S)-Practolol with better yield and enantiomeric excess.
Publisher

Journal
Year
Volume
1
Issue
1
Physical description
Dates
received
13 - 5 - 2015
online
20 - 1 - 2016
accepted
28 - 9 - 2015
Contributors
author
  • Department of
    Pharmaceutical Technology (Biotechnology), National Institute
    of Pharmaceutical Education and Research, Sector-67,,S. A. S.
    Nagar-160062, Punjab
  • Department of
    Pharmaceutical Technology (Biotechnology), National Institute
    of Pharmaceutical Education and Research, Sector-67,,S. A. S.
    Nagar-160062, Punjab
  • Department of
    Pharmaceutical Technology (Biotechnology), National Institute
    of Pharmaceutical Education and Research, Sector-67,,S. A. S.
    Nagar-160062, Punjab
  • Department of
    Pharmaceutical Technology (Biotechnology), National Institute
    of Pharmaceutical Education and Research, Sector-67,,S. A. S.
    Nagar-160062, Punjab
References
  • [1] Brew J., Baxter A.D., Bannister R.M., Use ofbeta-aminoalcohols in the treatment of inflammatorydisorders and pain, EP1993525 A1. 2008.
  • [2] (a) Siebert C.D., Hansicke A., Nagel T., Stereochemicalcomparison of nebivolol with other β-blockers, Chirality,2008, 20, 103-109. (b) Ellison K.E., Gandhi G., Optimisingthe use of beta-adrenoceptor antagonists in coronary arterydisease, Drugs, 2005, 65, 787-797.[Crossref]
  • [3] Baran D., Horn E.M., Hryniewicz K., Katz S.D., Effects ofbeta-blockers on neurohormonal activation in patients withcongestive heart failure, Drugs, 2000, 60, 997-1016.[Crossref]
  • [4] Teerlink J.R., Massie B.M., Beta-adrenergic blocker mortalitytrials in congestive heart failure, Am. J. Cardiol., 1999, 84,94-102][Crossref]
  • [5] Bredikhin A.A., Bredikhina Z.A., Zakharychev D.V., AkhatovaF.S., Krivolapov D., Litvinov I.A., Solid-state properties of1, 2-epoxy-3-(2-cyanophenoxy) propane, a conglomerateformingchiral drug precursor, Mendeleev Commun., 2006,16, 245-247.[Crossref]
  • [6] Masuda K., Tamagake K., Katsu T., Torigoe F., Saito K.,Hanioka N., Yamano S., Yamamoto S., Narimatsu S., Roles ofphenylalanine at position 120 and glutamic acid at position222 in the oxidation of chiral substrates by cytochrome P4502D6, Chirality, 2006, 18, 167-176.
  • [7] Leftheris K., Goodman M., Synthesis and beta-adrenergicantagonist activity of stereoisomeric practolol andpropranolol derivatives, J. Med. Chem., 1990, 33, 216-223.[Crossref]
  • [8] Kumar P., Naidu V., Gupta P., Application of hydrolytic kineticresolution (HKR) in the synthesis of bioactive compounds,Tetrahedron, 2007, 63, 2745–2785.[Crossref]
  • [9] Zelaszczyk D., Kiec-Kononowicz K., Biocatalytic approachesto optically active β-blockers, Curr. Med. Chem., 2007, 14,53-65.[WoS][Crossref]
  • [10] Sayyed I.A., Thakur V.V., Nikalje M.D., Dewkar G.K., KotkarS.P., Sudalai A., Asymmetric synthesis of aryloxypropanolaminesvia OsO4-catalyzed asymmetric dihydroxylation,Tetrahedron, 2005, 61, 2831-2838.[Crossref]
  • [11] Bredikhina Z.A., Akhatova F.S., Zakharychev D.V., BredikhinA.A., Spontaneous resolution amongst chiral orthocyanophenylglycerol derivatives: an effective preferentialcrystallization approach to a single enantiomer of theβ-adrenoblocker bunitrolol, Tetrahedron: Asymm., 2008, 19,1430-1435.[WoS][Crossref]
  • [12] Bredikhin A.A., Bredikhina Z.A., Zakharychev D.V., AkhatovaF.S., Krivolapov D.B., Litvinov I.A., Solid-state properties of1,2-epoxy-3-(2-cyanophenoxy)propane, a conglo-merateformingchiral drug precursor, Mendeleev Commun., 2006,16, 245-247.[Crossref]
  • [13] Cepanec I., Litvic M., Mikuldaš H., Bartolinčić A., Vinković V.,Calcium trifluoromethanesulfonate-catalysed aminolysis ofepoxides, Tetrahedron, 2003, 59, 2435-2439.[Crossref]
  • [14] Yadav J.S., Reddy B.V.S., Basak A.K., Narsaiah A.V.,Ionic liquid: a novel reaction medium for the synthesisof beta-amino alcohols, Tetrahedron Lett., 2003, 44,1047-1050.[Crossref]
  • [15] Kitaori K., Furukawa Y., Yoshimoto H., Otera J., Regioselectivenucleophilic reactions of phenols with oxiranesleading to enantiopure ß-blockers, Tetrahedron, 1999, 55,14381-14390.[Crossref]
  • [16] Borude V.S., Shah R.V., Shukla S.R., Synthesis of β-aminoalcohol derivatives from phenols in presence of phasetransfer catalyst and lipase biocatalyst, Curr. Chem. Lett.,2013, 2, 1-12.[Crossref]
  • [17] Calleri E., Temporini C., Furlanetto S., Loiodice F., FracchiollaG., Massolini G., Lipases for biocatalysis: development of achromatographic bioreactor, J. Pharm. Biomed. Anal., 2003,32, 715-724.[Crossref]
  • [18] Khmelnitsky Y.L., Rich J.O., Biocatalysis in nonaqueoussolvents, Curr. Opin. Chem. Biol., 1999, 3, 47-53.[Crossref]
  • [19] Ader U., Schneider M.P., Enzyme assisted preparation ofenantiomerically pure β-adrenergic blockers II. Buildingblocks of high optical purity and their synthetic conversion,Tetrahedron: Asymm., 1992, 3, 205-208.[Crossref]
  • [20] Jacobsen E.E., Andresen L.S., Anthonsen T., Immobilizationdoes not influence the enantioselectivity of CAL-B catalyzedkinetic resolution of secondary alcohols, Tetrahedron:Asymm., 2005, 16, 847–850.[Crossref]
  • [21] Ader U., Schneider M.P., Enzyme assisted preparation ofenantiomerically pure β-adrenergic blockers III. Opticallyactive chlorohydrin derivatives and their conversion,Tetrahedron: Asymm., 1992, 3, 521.524.[Crossref]
  • [22] Khan F.A., Dash J., Jain D., Prabhudas B., Rearrangementof 1,4,5,6-tetrahalo-7,7-dimethoxybicyclo
  • [2.2.1]hept-5-en-2-ones to phenolic derivatives, J. Chem. Soc., PerkinTransactions, 2001, 1, 3132-3134.
  • [23] Thakkar N.V., Banerji A.A., Bevinakatti, H.S., Chemoenzymaticsynthesis of S (-) Practolol, Biotechnol. Lett., 1995,17, 217-218.[Crossref]
  • [24] Bermudez J.L., Campo C.D., Salazar L., Llama E.F., Jose V.Sinisterra J.V., A New Application of Candida antarcticaLipase for Obtaining Natural Homochiral BBAs Aryloxypropanolamine,Tetrahedron: Asymm, 1996, 7, 2485-2488.[Crossref]
  • [25] Hudson E.P., Eppler R.K., Clark D.S., Biocatalysis insemi-aqueous and nearly anhydrous conditions, Curr. Opin.Biotechnol., 2005, 16, 637-643.[Crossref]
  • [26] Dordick J.S., Enzymatic catalysis in monophasic organicsolvents, Enzym. Microb. Technol., 1989, 11, 194-211.[Crossref]
  • [27] Khmelnitsky Y.L., Levashov A.V., Klyachko N.L., Martinek K.,Engineering biocatalytic systems in organic media with lowwater content, Enzym. Microb. Technol., 1988, 10, 710-724.[Crossref]
  • [28] Laane C., Boeren S., Vos K., Veeger C., Rules for optimizationof biocatalysis in organic solvents, Biotechnol. Bioeng.,2004, 30, 81-87.[Crossref]
  • [29] Gonzalo G.D., Brieva R., Sanchez V.M., Bayod M., GotorV., Enzymatic alkoxy-carbonylation reactions on theintermediate in the synthesis of (-)-paroxetine, transN-benzyloxycarbonyl-4-(4’-fluorophenyl)-3-hydroxymethylpiperidine,Tetrahedron: Asymm., 2003, 14, 1725.[Crossref]
  • [30] Ferraboschi P., Pecora F., Reza-Elahi S., Santaniello E.,Chemoenzymatic synthesis of (25R)- and (25S)-25-hydroxy-27-nor-cholesterol, a steroid bearing a secondary hydroxygroup in the side chain, Tetrahedron: Asymm., 1999, 10,2497-2500.[Crossref]
  • [31] Queiroz N., Nascimento M.G., Pseudomonas sp. lipaseimmobilized in polymers versus the use of free enzyme inthe resolution of (R,S)-methyl mandelate, Tetrahedron Lett.,2002, 43, 5225-5227.[Crossref]
  • [32] Gotor-Fernández V., Ferrero M., Fernández S., Gotor V.,1α,25-Dihydroxyvitamin D3 A-Ring Precursors: Studies onregioselective enzymatic alkoxycarbonylation reactions oftheir stereoisomers. Chemoenzymatic synthesis of A-ringsynthon carbamate derivatives, including carbazates andpolyamino carbamates, J. Org. Chem., 1999, 64, 7504 -7510.
  • [33] Egri G., Baitz-Gacs E., Poppe L., Kinetic resolution of2-acylated-1,2-diols by lipase-catalyzed enantiomerselective acylation, Tetrahedron Asymm., 1996, 7,1437-1448.[Crossref]
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_1515_boca-2015-0006
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.