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Tytuł artykułu

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

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Warianty tytułu
Języki publikacji
EN
Abstrakty
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.
Wydawca

Czasopismo
Rocznik
Tom
1
Numer
1
Opis fizyczny
Daty
otrzymano
2015-05-13
zaakceptowano
2015-09-28
online
2016-01-20
Twórcy
autor
  • 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
Bibliografia
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Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_1515_boca-2015-0006
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