Literature DB >> 915911

Structure of warfarin in solution.

E J Valente, E C Lingafelter, W R Porter, W F Trager.   

Abstract

Warfarin in solution is shown to consist of three interconverting tautomeric structures, two of which are cyclic diastereomeric hemiketals, while the third and minor component is the open-chain intermediate form. The configurations of all the tautomers as well as the major conformations of the cyclic tautomers are assigned. The assignments are supported by comparison with the chemical shift and coupling constant parameters of structurally fixed model compounds.

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Year:  1977        PMID: 915911     DOI: 10.1021/jm00221a025

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  9 in total

Review 1.  Warfarin: history, tautomerism and activity.

Authors:  William R Porter
Journal:  J Comput Aided Mol Des       Date:  2010-03-30       Impact factor: 3.686

2.  Tautomerism of Warfarin: Combined Chemoinformatics, Quantum Chemical, and NMR Investigation.

Authors:  Laura Guasch; Megan L Peach; Marc C Nicklaus
Journal:  J Org Chem       Date:  2015-09-25       Impact factor: 4.354

3.  Warfarin glycosylation invokes a switch from anticoagulant to anticancer activity.

Authors:  Pauline Peltier-Pain; Shannon C Timmons; Agnès Grandemange; Etienne Benoit; Jon S Thorson
Journal:  ChemMedChem       Date:  2011-06-28       Impact factor: 3.466

4.  Multiple UDP-glucuronosyltransferases in human liver microsomes glucuronidate both R- and S-7-hydroxywarfarin into two metabolites.

Authors:  C Preston Pugh; Dakota L Pouncey; Jessica H Hartman; Robert Nshimiyimana; Linda P Desrochers; Thomas E Goodwin; Gunnar Boysen; Grover P Miller
Journal:  Arch Biochem Biophys       Date:  2014-10-19       Impact factor: 4.013

5.  Inclusion complexation of warfarin with cyclodextrins to improve some pharmaceutical characteristics.

Authors:  S Y Lin; J C Yang
Journal:  Pharm Weekbl Sci       Date:  1986-08-22

6.  Enumeration of ring-chain tautomers based on SMIRKS rules.

Authors:  Laura Guasch; Markus Sitzmann; Marc C Nicklaus
Journal:  J Chem Inf Model       Date:  2014-09-09       Impact factor: 4.956

7.  Sequestration Effect on the Open-Cyclic Switchable Property of Warfarin Induced by Cyclodextrin: Time-Resolved Fluorescence Study.

Authors:  Naji Al-Dubaili; Na'il Saleh
Journal:  Molecules       Date:  2017-08-11       Impact factor: 4.411

8.  The effect of CYP2C9*2, CYP2C9*3, and VKORC1-1639 G>A polymorphism in patients under warfarin therapy in city of Kermanshah.

Authors:  Zohreh Hosseinkhani; Mona Sadeghalvad; Fathemeh Norooznezhad; Reza Khodarahmi; Mohammad Fazilati; Azadeh Mahnam; Ali Fattahi; Kamran Mansouri
Journal:  Res Pharm Sci       Date:  2018-08

9.  Consequences of morphology on molecularly imprinted polymer-ligand recognition.

Authors:  Annika M Rosengren; Björn C G Karlsson; Ian A Nicholls
Journal:  Int J Mol Sci       Date:  2013-01-09       Impact factor: 5.923

  9 in total

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