Yet little detail is known about the molecular interactions between 4-hydroxycoumarins with vitamin K epoxide reductase (VKER), inhibition of which produces a deficiency of vitamin K and consequently a deficiency of vitamin K-dependent proteins involved in thrombus formation.

Herein, this was the first application of bio-catalytic synthesis and fluorescence for the determination of warfarin.


Asymmetric synthesis of warfarin by the Michael addition of 4-hydroxycoumarin to benzylideneacetone.

4-Hydroxycoumarins such as warfarin 1 have been the mainstay of oral anticoagulation therapy for over 20 years.

Continuous Flow Stereoselective Synthesis of (S)-Warfarin The same catalytic packed-bed reactor was used for the preparation of (S)-warfarin 107 under continuous flow conditions (Scheme ).A solution of 4-OH-coumarin 104, benzalacetone105, and trifluoroacetic acid as a cocatalyst in dioxane was flowed into the reactor containing the polystyrene-supported 9-amino-epi-quinine 122. Royal Society of Chemistry Warfarin acts by inhibiting the synthesis of vitamin K-dependent clotting factors, which include Factors II, VII, IX, and X, and the anticoagulant proteins C and S. Vitamin K is an essential cofactor for the post ribosomal synthesis of the vitamin K-dependent clotting factors. Kucherenko AS, Lisnyak VG, Kostenko AA, Kochetkov SV, Zlotin SG.Org Biomol Chem. This file is licensed under the Creative Commons Attribution-Share Alike 3.0 Unported license. Unable to load your delegates due to an error 2012 Apr 20;14(8):2038-41. doi: 10.1021/ol300489q. Amitava Dasgupta PhD, DABCC, Amer Wahed MD, in Clinical Chemistry, Immunology and Laboratory Quality Control, 2014. Epub 2012 Apr 6.Chem Rec. 20.4 Pharmacogenomics and Warfarin Therapy. Warfarin, also called Coumadin, is an anticoagulant.

Recyclability of the developed catalysts and synthetic utility of the prepared Michael adducts for asymmetric synthesis of potential chiral medications via acylation reactions were demonstrated. Clipboard, Search History, and several other advanced features are temporarily unavailable.

In this experiment, students synthesize either enantiomer of warfarin, a widely used anticoagulant, in a single step from inexpensive starting materials. The enantioselective synthesis of drugs is of fundamental importance in the pharmaceutical industry.

2016 Oct 18;14(41):9751-9759. doi: 10.1039/c6ob01606e.Org Biomol Chem. : You are free: to share – to copy, distribute and transmit the work; to remix – to adapt the work; Under the following conditions: attribution – You must give appropriate credit, provide a link to the license, and indicate if changes were made.

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COVID-19 is an emerging, rapidly evolving situation. 2016 Apr;16(2):897-906. doi: 10.1002/tcr.201500266. Both enantiomers of the anticoagulant warfarin and its analogs were prepared in up to 96% yield and with 96% ee.

However, the activity and metabolism of both enantiomeric forms are dissimilar.

2012 Oct 28;10(40):8125-31. doi: 10.1039/c2ob26334c.Molecules.

Unable to load your collection due to an error Stereoselectivity is induced by a commercial organocatalyst, (R,R)- or (S,S)-1,2-diphenylethylenediamine.

Name must be less than 100 characters The application of enantiomerically pure (We use cookies to help provide and enhance our service and tailor content and ads.

Epub 2016 Mar 10. The asymmetric Michael addition of 4-hydroxycoumarin to α,β-unsaturated ketones on water without organic co-solvents is reported to be catalysed by organic primary amines. An anticoagulant helps prevent the formation of blood clots.



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Recyclability of the developed catalysts and synthetic utility of the prepared Michael adducts for asymmetric synthesis of potential chiral medications via … Novel C2-symmetric N,N'-bis(2-amino-1,2-diphenylethyl)squaramides with 1,2-di(pyridin-2-yl)ethane and 1,2-diphenylethane spacer groups were designed and applied as organocatalysts in asymmetric additions of 4-hydroxycoumarin and 4-hydroxy-6-methyl-2H-pyran-2-one to α,β-unsaturated ketones.

Royal Society of Chemistry

Furthermore, the spectrofluorometry was used to detect the concentration of warfarin with a linear range and detection limit (3σ/k) of 0.04-12.0μmolL-1 (R2=0.994) and 0.01μmolL-1, respectively. Both enantiomers of the anticoagulant warfarin and its analogs were prepared in up to 96% yield and with 96% ee.



As one of the most effective anticoagulants, warfarin has been introduced for clinical use (warfarin®, jantoven®, uniwarfin®, coumadin®, marevan®) as a racemate. By continuing you agree to the Copyright © 2020 Elsevier B.V. or its licensors or contributors. ScienceDirect ® is a registered trademark of Elsevier B.V.Asymmetric synthesis of warfarin and its analogues on waterCopyright © 2014 Elsevier Ltd. All rights reserved.ScienceDirect ® is a registered trademark of Elsevier B.V. 2016 Oct 14;21(10):1327. doi: 10.3390/molecules21101327.Org Lett.