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      Synthetic Approaches and Biological Activities of 4-Hydroxycoumarin Derivatives

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          Abstract

          The main purpose of this review is to summarize recent chemical syntheses and structural modifications of 4-hydroxycoumarin and its derivatives, of interest due to their characteristic conjugated molecular architecture and biological activities.

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          Most cited references47

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          Pharmacokinetics of eight anticoagulant rodenticides in mice after single oral administration.

          Sven P. F. I. van Ommeren, S Croubels, Paula A. Bousquet … (2008)
          The first aim of the study was to investigate the pharmacokinetics of eight anticoagulant rodenticides (brodifacoum, bromadiolone, chlorophacinone, coumatetralyl, difenacoum, difethialone, flocoumafen and warfarin) in plasma and liver of the mouse after single oral administration. Eight groups of mice dosed orally with a different anticoagulant rodenticide in a dose equal to one-half the lethal dose 50 (LD(50)), were killed at various times up to 21 days after administration. The eight anticoagulant rodenticides were assayed in plasma and liver by an LC-ESI-MS/MS method. Depending on the compound, the limit of quantification was set at 1 or 5 ng/mL in plasma. In liver, the limit of quantification was set at 250 ng/g for coumatetralyl and warfarin and at 100 ng/g for the other compounds. The elimination half-lives in plasma for first-generation rodenticides were shorter than those for second-generation rodenticides. Coumatetralyl, a first-generation product, had a plasma elimination half-life of 0.52 days. Brodifacoum, a second-generation product, showed a plasma elimination half-life of 91.7 days. The elimination half-lives in liver varied from 15.8 days for coumatetralyl to 307.4 days for brodifacoum. The second aim of the study was to illustrate the applicability of the developed method in a clinical case of a dog suspected of rodenticide poisoning.
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            Novel 4-hydroxycoumarin anticoagulants active against resistant rats.

            M Hadler, R Shadbolt (1975)
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              Pharmacogenomics of 4-hydroxycoumarin anticoagulants.

              Allan E. Rettie, N Au (2007)
              Oral anticoagulants of the 4-hydroxycoumarin class, typified by warfarin, are used worldwide to treat thromboembolic disease. These drugs show the beneficial attributes of high efficacy and low cost, but patient management can be complicated by their narrow therapeutic index and wide inter-individual variability in dosing. Our understanding of the latter complication has improved significantly in recent years due to intense investigation of genetic factors influencing drug pharmacokinetics (CYP2C9) and pharmacodynamic response (VKORC1). In particular, the discovery of polymorphisms in the VKORC1 gene that strongly impact oral anticoagulant dose has heightened expectations that genetic testing for a relatively small cadre of warfarin-response genes might substantially enhance patient care in this area, especially during the initiation phase of therapy. However, enthusiasm for genotype-based dosing of oral anticoagulants must be balanced against the ready availability of both a simple phenotypic test (prothrombin time) and an antidote to over-anticoagulation (vitamin K). Wide-spread acceptance of genetically based tests for establishing therapy with warfarin and its congeners will likely require additional evidence that such an approach offers protection against a variety of negative anticoagulation outcomes, especially severe bleeding, as well as offering utility across many racial populations. This article will review recent events in these and other related areas.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: Molecular Diversity Preservation International
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 23 November 2009
                Publication date Collection: November 2009
                Volume: 14
                Issue: 11
                Pages: 4790-4803
                Affiliations
                [1 ]Ewha Global Challenge, BK21 and Medical Research Institute, School of Medicine, Ewha Womans University, Seoul 158–710, Korea; E-Mail: jcjung10@ 123456yahoo.co.kr (J.-C.J.)
                [2 ]Department of Chemistry, Institute for Basic Sciences, College of Natural Sciences, Chungbuk National University, Cheongju 361–763, Chungbuk, Korea
                Author notes
                [* ]Author to whom correspondence should be addressed; E-Mail: ospark@ 123456cbnu.ac.kr .
                Article
                Publisher ID: molecules-14-04790
                DOI: 10.3390/molecules14114790
                PMC ID: 6254719
                SO-VID: bd89933b-9e6e-45e4-b410-e4338bf79c0e
                Copyright © © 2009 by the authors;
                License:

                licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

                History
                Date received : 19 October 2009
                Date revision received : 16 November 2009
                Date accepted : 18 November 2009
                Categories
                Subject: Review

                Keywords: 4-hydroxycoumarin,anticoagulant,rodenticide,ring cyclization,tetralone,coupling reaction
                Data availability:
                Keywords: 4-hydroxycoumarin, anticoagulant, rodenticide, ring cyclization, tetralone, coupling reaction

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