4-Hydroxycoumarin

The herbs of Guazuma ulmifolia

Microbial biosynthesis of the anticoagulant precursor 4-hydroxycoumarin.[Pubmed:24129598]

Nat Commun. 2013;4:2603.

4-Hydroxycoumarin (4HC) type anticoagulants (for example, warfarin) are known to have a significant role in the treatment of thromboembolic diseases--a leading cause of patient morbidity and mortality worldwide. 4HC serves as an immediate precursor of these synthetic anticoagulants. Although 4HC was initially identified as a naturally occurring product, its biosynthesis has not been fully elucidated. Here we present the design, validation, in vitro diagnosis and optimization of an artificial biosynthetic mechanism leading to the microbial biosynthesis of 4HC. Remarkably, function-based enzyme bioprospecting leads to the identification of a characteristic FabH-like quinolone synthase from Pseudomonas aeruginosa with high efficiency on the 4HC-forming reaction, which promotes the high-level de novo biosynthesis of 4HC in Escherichia coli (~500 mg l(-)(1) in shake flasks) and further in situ semisynthesis of warfarin. This work has the potential to be scaled-up for microbial production of 4HC and opens up the possibility of biosynthesizing diverse coumarin molecules with pharmaceutical importance.

Larvicidal activity of 4-hydroxycoumarin derivatives against Aedes aegypti.[Pubmed:21043993]

Pharm Biol. 2011 Feb;49(2):190-3.

CONTEXT: Coumarins are natural substances found in a variety of plants. It is well known that plant-derived natural products are extensively used as biologically active compounds. Among them, coumarins were the first preservatives used by man, originally in their natural state within plant tissues and then as natural materials obtained by water distillation. During our search for new types of coumarin derivatives possessing a larvicidal activity, we investigated the synthesis of 4-Hydroxycoumarin derivatives. OBJECTIVE: The coumarin derivatives were synthesized and the structure determination and larvicidal effects were studied. MATERIALS AND METHODS: The structure analyses were conducted by nuclear magnetic resonance (NMR), and mass (MS) spectroscopy revealed that the coumarin derivatives were obtained in good yields, and the eight coumarin derivatives were 3-{1,2,3,4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyl}-1-naphthalen-1-on (1), 3-{1,2,3,4-tetrahydro-3-[4-(4-trifluoro methylbenzyloxy)phenyl}-1-naphthalen-1-ol (2), brodifacoum (3), difethialone (4), bromadiolone (5), 4-hydroxy-3-(1,2,3,4-tetrahydronaphthalen-1-yl)-2H-chromen-2-one (coumatetralyl) (6), cis-flocoumafen (7) and trans-flocoumafen (8). RESULTS: The compounds were tested against the F(21) laboratory strain of Aedes aegypti L. Brodifacoum and cis-flocoumafen mediated strong activity with an LC(50) values of 8.23 and 9.34 ppm, respectively. DISCUSSION AND CONCLUSION: The above indicates that brodifacoum may play a more important role in the toxicity of 4-Hydroxycoumarin derivatives.

Synthesis and anticholinergic activity of 4-hydroxycoumarin derivatives containing substituted benzyl-1,2,3-triazole moiety.[Pubmed:26010139]

Chem Biol Drug Des. 2015 Nov;86(5):1215-20.

A series of 4-Hydroxycoumarin-derived compounds 8a-p containing N-benzyl-1,2,3-triazole motif were designed as AChE inhibitors. The title compounds were obtained conveniently using multicomponent click reaction. The in vitro anticholinesterase evaluation of synthesized compounds against AChE and BuChE showed that some of them are potent and selective inhibitors of AChE. Among them, 2-chlorobenzyl derivative 8k showed the most potent activity against AChE (IC50 = 0.18 mum). Its activity was also superior to that of standard drug tacrine. The kinetic study and molecular docking simulation of the most potent compound 8k were also described.

Effect of different C3-aryl substituents on the antioxidant activity of 4-hydroxycoumarin derivatives.[Pubmed:21964183]

Bioorg Med Chem. 2011 Nov 1;19(21):6233-8.

The antioxidant activity of 4-Hydroxycoumarin synthetic derivatives and 4-methylumbelliferone were determined taking 4-Hydroxycoumarin as the reference compound. Six 3-aryl-4-Hydroxycoumarin derivatives were synthesized from 4-Hydroxycoumarin as precursor in order to evaluate changes in their antioxidant properties due to C3-aryl substituent nature. Free radical scavenging capacities of these compounds against two different species DPPH(.) and ABTS(.+) and the protecting ability towards the beta-carotene-linoleic acid co-oxidation enzymatically induced by lipoxygenase were measured. In addition, the relationship between the activities of these molecules against DPPH radical and the bond dissociation energy of O-H (BDE) calculated using methods of computational chemistry was evaluated.

4-Hydroxycoumarin, a coumarin derivative, is one of the most versatile heterocyclic scaffolds and is frequently applied in the synthesis of various organic compounds. 4-Hydroxycoumarin possesses both electrophilic and nucleophilic properties. 4-Hydroxycoumarin derivatives are employed as the anticoagulant, antibacterial, antifungal, antiviral, antitumor, antiprotozoal, insecticidal, antimycobacterial, antimutagenic, antioxidant, anti-inflammatory agents, HIV protease inhibitors and tyrosine kinase inhibitors.

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