Disease relevance of 22105-09-5

• Cholestasis may occur in response to exposure to derivations of 4-hydroxycoumarin [1].
• This investigation reports on the important finding of a carboxamide functionally appropriately added to the 4-hydroxycoumarin and the 4-hydroxy-2-pyrone templates which resulted in a new promising series of nonpeptidic HIV protease inhibitors with improved enzyme-binding affinity [2].
• The two best inhibitors found, NSC 32180, a "dimer" of 4-hydroxycoumarin, and NSC 117027, a "tetramer" of 2-hydroxy quinone, had ID50 values of 0.32 and 0.75 microM for HIV-1 protease inhibition, respectively, and two other inhibitors had ID50 values close to 1 microM [3].
• Bromadiolone (BRD), a substituted 4-hydroxycoumarin derivative, is known to possess anti-coagulant activity with acute toxicity [4].
• This study determined the in vitro effects of 4-hydroxycoumarin (4-HC) employing the melanoma cell line B16-F10 and the non-malignant fibroblastic cell line B82 [5].

High impact information on 22105-09-5

• Greater than 99% of the covalent incorporation is precluded by the addition of 15 microM dicoumarol, consistent with the specific labeling of the 4-hydroxycoumarin binding site of this enzyme by this photoaffinity reagent [6].
• Two missense mutations on one allele of UGT1A6 (UGT1A6*2) result in T181A and R184S amino acid substitutions and reduced activity against phenolics, such as 4-nitrophenol, 4-hydroxycoumarin and butylated hydroxy anisole [7].
• From a broad screening program, the 4-hydroxycoumarin phenprocoumon (I) was previously identified as a lead template with HIV protease inhibitory activity [8].
• Sterigmatocystin, coumarin, and 4-hydroxycoumarin did not give a cross-reaction with the antibody [9].
• In this study we investigated biological activity of ferulenol, a prenylated 4-hydroxycoumarin from Ferula communis [10].

Chemical compound and disease context of 22105-09-5

• Warfarin is a 4-hydroxycoumarin anticoagulant drug used for the prevention and management of thromboembolic and vascular diseases [11].
• Addition of the MAS and CIM-MAS increased the developmental toxicities of coumarin and, particularly, 4-hydroxycoumarin [12].
• Acute toxicity of ferulenol, a 4-hydroxycoumarin isolated from Ferula communis L [13].

Biological context of 22105-09-5

• The outstanding activity of 1a, its low toxicity, and the evidence for definite structure-activity relationships make this prenylated 4-hydroxycoumarin an interesting antibacterial chemotype worth further investigation [14].
• Methylation of 4-hydroxycoumarin with diazomethane [15].

Anatomical context of 22105-09-5

• A liquid chromatographic method was developed for the analysis of indandione and 4-hydroxycoumarin anticoagulant rodenticides in blood serum and liver [16].
• Synthesis of 4-hydroxycoumarin and 2,4-quinolinediol derivatives and evaluation of their effects on the viability of HepG2 cells and human hepatocytes culture [17].
• Vitamin K epoxide reductase (VKOR) activity in liver microsomes from a susceptible and a genetically warfarin-resistant strain of mice (Mus Musculus domesticus) was analyzed to determine the mechanism of resistance to this 4-hydroxycoumarin derivative [18].
• 4-Hydroxycoumarin disorganizes the actin cytoskeleton in B16-F10 melanoma cells but not in B82 fibroblasts, decreasing their adhesion to extracellular matrix proteins and motility [5].
• Furthermore, the increased toxicity of coumarin or 4-hydroxycoumarin following co-incubation with CHO-treated microsomes indicated that highly toxic epoxide intermediates may be produced from oxidative P-450 metabolism and that epoxide hydrolase may play a role in detoxification of the reactive intermediates [12].

Associations of 22105-09-5 with other chemical compounds

• The fluorescence spectroscopic behavior of bromadiolone (anticoagulant rodenticide), a substituted 4-hydroxycoumarin derivative, was investigated in water and in organized media like micelles and cyclodextrins [19].
• Electrooxidation of iodide in the presence of 4-hydroxycoumarin: application to a simple coulometric titration of 4-hydroxycoumarin [20].

Gene context of 22105-09-5

• 4-Hydroxycoumarin in heterocyclic synthesis. Part III. Synthesis of some new pyrano[2,3-d]pyrimidine, 2-substitute [21].
• 4-Hydroxycoumarin and coumarin had no effect on either 5-lipoxygenase or cyclooxygenase at concentrations of up to 1 mM [22].

Analytical, diagnostic and therapeutic context of 22105-09-5

• Multicomponent determination of 4-hydroxycoumarin anticoagulant rodenticides in blood serum by liquid chromatography with fluorescence detection [23].
• According to the obtained results, a new and simple coulometric titration method with potentiometric end-point detection for the determination of 4-hydroxycoumarin (1) is presented [20].

References