Coumarin derivatives
Organic compounds derived from coumarin / From Wikipedia, the free encyclopedia
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]