Английская Википедия:Coumarin derivatives
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.
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:
- brodifacoum[2][3]
- bromadiolone[4]
- difenacoum[5]
- auraptene
- ensaculin
- phenprocoumon (Marcoumar)
- PSB-SB-487
- PSB-SB-1202
- scopoletin can be isolated from the bark of Shorea pinanga[6]
- warfarin (Coumadin)
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]
References
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite web
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite web
- ↑ Шаблон:Cite web
- ↑ Шаблон:Cite journal
- ↑ 7,0 7,1 7,2 Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ 9,0 9,1 Шаблон:Cite web
- ↑ Шаблон:Cite web
- ↑ 11,0 11,1 Шаблон:Cite web
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ 14,0 14,1 Шаблон:Cite bookШаблон:ISBN missing
- ↑ 15,0 15,1 Шаблон:Cite bookШаблон:ISBN missing
- ↑ 16,0 16,1 16,2 Шаблон:Cite bookШаблон:ISBN missing
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite patent
