Coumarin derivatives

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Chemical structure of coumarin Coumarin acsv.svg
Chemical structure of coumarin

Coumarin derivatives are derivatives of coumarin and are considered phenylpropanoids. [1] Among the most important derivatives are the 4-hydroxycoumarins, which exhibit anticoagulant properties, a characteristic not present for coumarin itself.

Contents

Some naturally occurring coumarin derivatives include umbelliferone (7-hydroxycoumarin), aesculetin (6,7-dihydroxycoumarin), herniarin (7-methoxycoumarin), psoralen and imperatorin.

4-Phenylcoumarin is the backbone of the neoflavones, a type of neoflavonoids.

Coumarin pyrazole hybrids have been synthesized from hydrazones, carbazones and thiocarbazones via Vilsmeier Haack formylation reaction.

Compounds derived from coumarin are also called coumarins or coumarinoids; this family includes:

Coumarin is transformed into the natural anticoagulant dicoumarol by a number of species of fungi. [7] This occurs as the result of the production of 4-hydroxycoumarin, then further (in the presence of naturally occurring formaldehyde) into the actual anticoagulant dicoumarol, a fermentation product and mycotoxin. Dicoumarol was responsible for the bleeding disease known historically as "sweet clover disease" in cattle eating moldy sweet clover silage. [7] [8] In basic research, preliminary evidence exists for coumarin having various biological activities, including anti-inflammatory, anti-tumor, antibacterial, and antifungal properties, among others. [7]

Uses

Medicine

Warfarin a coumarin with brand name, Coumadin, is a prescription drug used as an anticoagulant to inhibit formation of blood clots, and so is a therapy for deep vein thrombosis and pulmonary embolism. [9] [10] [11] It may be used to prevent recurrent blood clot formation from atrial fibrillation, thrombotic stroke, and transient ischemic attacks. [11]

Coumarins have shown some evidence of biological activity and have limited approval for few medical uses as pharmaceuticals, such as in the treatment of lymphedema. [9] [12] Both coumarin and 1,3-indandione derivatives produce a uricosuric effect, presumably by interfering with the renal tubular reabsorption of urate. [13]

Laser dyes

Coumarin dyes are extensively used as gain media in blue-green tunable organic dye lasers. [14] [15] [16] Among the various coumarin laser dyes are coumarins 480, 490, 504, 521, 504T, and 521T. [16] Coumarin tetramethyl laser dyes offer wide tunability and high laser gain, [17] [18] and they are also used as active medium in coherent OLED emitters. [19] [14] [15] [16] and as a sensitizer in older photovoltaic technologies. [20]

Related Research Articles

<span class="mw-page-title-main">Anticoagulant</span> Class of drugs

An anticoagulant, commonly known as a blood thinner, is a chemical substance that prevents or reduces the coagulation of blood, prolonging the clotting time. Some occur naturally in blood-eating animals, such as leeches and mosquitoes, which help keep the bite area unclotted long enough for the animal to obtain blood.

<span class="mw-page-title-main">Warfarin</span> Anticoagulant medication

Warfarin is an anticoagulant used as a medication under several brand names including Coumadin. While the drug is described as a "blood thinner", it does not reduce viscosity but rather inhibits coagulation. Accordingly, it is commonly used to prevent blood clots in the circulatory system such as deep vein thrombosis and pulmonary embolism, and to protect against stroke in people who have atrial fibrillation, valvular heart disease, or artificial heart valves. Less commonly, it is used following ST-segment elevation myocardial infarction (STEMI) and orthopedic surgery. It is usually taken by mouth, but may also be administered intravenously.

<span class="mw-page-title-main">Dye laser</span> Equipment using an organic dye to emit coherent light

A dye laser is a laser that uses an organic dye as the lasing medium, usually as a liquid solution. Compared to gases and most solid state lasing media, a dye can usually be used for a much wider range of wavelengths, often spanning 50 to 100 nanometers or more. The wide bandwidth makes them particularly suitable for tunable lasers and pulsed lasers. The dye rhodamine 6G, for example, can be tuned from 635 nm (orangish-red) to 560 nm (greenish-yellow), and produce pulses as short as 16 femtoseconds. Moreover, the dye can be replaced by another type in order to generate an even broader range of wavelengths with the same laser, from the near-infrared to the near-ultraviolet, although this usually requires replacing other optical components in the laser as well, such as dielectric mirrors or pump lasers.

<span class="mw-page-title-main">Coumarin</span> Aromatic chemical compound

Coumarin or 2H-chromen-2-one is an aromatic organic chemical compound with formula C9H6O2. Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring −(CH)=(CH)−(C=O)−O−, forming a second six-membered heterocycle that shares two carbons with the benzene ring. It belongs to the benzopyrone chemical class and considered as a lactone.

<i>Dipteryx odorata</i> Species of flowering tree in the pea family

Dipteryx odorata is a species of flowering tree in the pea family, Fabaceae. The tree is native to Northern South America and is semi-deciduous. Its seeds are known as tonka beans. They are black and wrinkled and have a smooth, brown interior. They have a strong fragrance similar to sweet woodruff due to their high content of coumarin.

<span class="mw-page-title-main">Warfarin necrosis</span> Medical condition

Warfarin-induced skin necrosis is a condition in which skin and subcutaneous tissue necrosis occurs due to acquired protein C deficiency following treatment with anti-vitamin K anticoagulants.

Karl Paul Gerhard Link was an American biochemist best known for his discovery of the anticoagulant warfarin.

<span class="mw-page-title-main">Acenocoumarol</span> Anticoagulant

Acenocoumarol is an anticoagulant that functions as a vitamin K antagonist. It is a derivative of coumarin and is generic, so is marketed under many brand names worldwide.

<span class="mw-page-title-main">Dicoumarol</span> Chemical compound

Dicoumarol (INN) or dicumarol (USAN) is a naturally occurring anticoagulant drug that depletes stores of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.

<span class="mw-page-title-main">4-Hydroxycoumarins</span> Group of anticoagulant drugs

4-Hydroxycoumarins are a class of vitamin K antagonist (VKA) anticoagulant drug molecules. Chemically, they are derived from coumarin by adding a hydroxy group at the 4 position to obtain 4-hydroxycoumarin, then adding a large aromatic substituent at the 3-position. The large 3-position substituent is required for anticoagulant activity.

<span class="mw-page-title-main">Brodifacoum</span> Chemical compound

Brodifacoum is a highly lethal 4-hydroxycoumarin vitamin K antagonist anticoagulant poison. In recent years, it has become one of the world's most widely used pesticides. It is typically used as a rodenticide, but is also used to control larger pests such as possums.

<span class="mw-page-title-main">Bromadiolone</span> Chemical compound

Bromadiolone is a potent anticoagulant rodenticide. It is a second-generation 4-hydroxycoumarin derivative and vitamin K antagonist, often called a "super-warfarin" for its added potency and tendency to accumulate in the liver of the poisoned organism. When first introduced to the UK market in 1980, it was effective against rodent populations that had become resistant to first generation anticoagulants.

<span class="mw-page-title-main">F. J. Duarte</span> Laser physicist and author/editor

Francisco Javier "Frank" Duarte is a laser physicist and author/editor of several books on tunable lasers.

Beam expanders are optical devices that take a collimated beam of light and expand its width.

<span class="mw-page-title-main">Vitamin K antagonist</span>

Vitamin K antagonists (VKA) are a group of substances that reduce blood clotting by reducing the action of vitamin K. The term "vitamin K antagonist" is technically a misnomer, as the drugs do not directly antagonize the action of vitamin K in the pharmacological sense, but rather the recycling of vitamin K. Vitamin K antagonists (VKAs) have been the mainstay of anticoagulation therapy for more than 50 years.

<span class="mw-page-title-main">Solid-state dye laser</span>

A solid-state dye laser (SSDL) is a solid-state lasers in which the gain medium is a laser dye-doped organic matrix such as poly(methyl methacrylate) (PMMA), rather than a liquid solution of the dye. These lasers are also referred to as solid-state organic lasers and solid-state dye-doped polymer lasers.

<span class="mw-page-title-main">Multiple-prism grating laser oscillator</span>

Multiple-prism grating laser oscillators, or MPG laser oscillators, use multiple-prism beam expansion to illuminate a diffraction grating mounted either in Littrow configuration or grazing-incidence configuration. Originally, these narrow-linewidth tunable dispersive oscillators were introduced as multiple-prism Littrow (MPL) grating oscillators, or hybrid multiple-prism near-grazing-incidence (HMPGI) grating cavities, in organic dye lasers. However, these designs were quickly adopted for other types of lasers such as gas lasers, diode lasers, and more recently fiber lasers.

<span class="mw-page-title-main">Laser dye</span> Dye used as a laser medium

A Laser dye is a dye used as laser medium in a dye laser.

<span class="mw-page-title-main">4-Hydroxycoumarin</span> Chemical compound

4-Hydroxycoumarin is a coumarin derivative with a hydroxy group at the 4-position.

<span class="mw-page-title-main">Organic laser</span> Laser that uses a carbon-based material as the gain medium

An organic laser is a laser which uses an organic material as the gain medium. The first organic laser was the liquid dye laser. These lasers use laser dye solutions as their gain media.

References

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