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Coumarin derivatives

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"Coumarins" redirects here. For the class of anticoagulants and rodenticides specifically, see 4-Hydroxycoumarins. For the parent compound, see Coumarin.
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.

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

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Medicine

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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

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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

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  1. ^ Jacobowitz, Joseph R.; Weng, Jing-Ke (2020-04-29). "Exploring Uncharted Territories of Plant Specialized Metabolism in the Postgenomic Era". Annual Review of Plant Biology. 71 (1). Annual Reviews: 631–658. doi:10.1146/annurev-arplant-081519-035634. ISSN 1543-5008. PMID 32176525. S2CID 212740956.
  2. ^ International Programme on Chemical Safety. "Brodifacoum (pesticide data sheet)". Archived from the original on 2006-12-09. Retrieved 2006-12-14.
  3. ^ Laposata, M; Van Cott, E. M.; Lev, M. H. (2007). "Case 1-2007—A 40-Year-Old Woman with Epistaxis, Hematemesis, and Altered Mental Status". New England Journal of Medicine. 356 (2): 174–82. doi:10.1056/NEJMcpc069032. PMID 17215536.
  4. ^ International Programme on Chemical Safety. "Bromadiolone (pesticide data sheet)". Archived from the original on 2006-12-21. Retrieved 2006-12-14.
  5. ^ International Programme on Chemical Safety. "Difenacoum (health and safety guide)". Retrieved 2006-12-14.
  6. ^ Syah, Y. M.; et al. (2009). "A modified oligostilbenoid, diptoindonesin C, from Shorea pinanga Scheff". Natural Product Research. 23 (7): 591–594. doi:10.1080/14786410600761235. PMID 19401910. S2CID 20216115.
  7. ^ a b c Venugopala, K. N.; Rashmi, V; Odhav, B (2013). "Review on Natural Coumarin Lead Compounds for Their Pharmacological Activity". BioMed Research International. 2013: 1–14. doi:10.1155/2013/963248. PMC 3622347. PMID 23586066.
  8. ^ Bye, A.; King, H. K. (1970). "The biosynthesis of 4-hydroxycoumarin and dicoumarol by Aspergillus fumigatus Fresenius". Biochemical Journal. 117 (2): 237–45. doi:10.1042/bj1170237. PMC 1178855. PMID 4192639.
  9. ^ a b "Coumarin". PubChem, National Library of Medicine, US National Institutes of Health. 4 April 2019. Retrieved 13 April 2019.
  10. ^ "Coumarins and indandiones". Drugs.com. 2016. Retrieved 24 December 2016.
  11. ^ a b "Warfarin". Drugs.com. 7 March 2019. Retrieved 13 April 2019.
  12. ^ Farinola, N.; Piller, N. (June 1, 2005). "Pharmacogenomics: Its role in re-establishing coumarin as treatment for lymphedema". Lymphatic Research and Biology. 3 (2): 81–86. doi:10.1089/lrb.2005.3.81. PMID 16000056.
  13. ^ Christensen, Flemming (1964-01-12). "Uricosuric Effect of Dicoumarol". Acta Medica Scandinavica. 175 (4): 461–468. doi:10.1111/j.0954-6820.1964.tb00594.x. ISSN 0954-6820. PMID 14149651.
  14. ^ a b Schäfer, F. P., ed. (1990). Dye Lasers (3rd ed.). Berlin: Springer-Verlag.[ISBN missing]
  15. ^ a b Duarte, F. J.; Hillman, L. W., eds. (1990). Dye Laser Principles. New York: Academic.[ISBN missing]
  16. ^ a b c Duarte, F. J. (2003). "Appendix of Laser Dyes". Tunable Laser Optics. New York: Elsevier-Academic.[ISBN missing]
  17. ^ Chen, C. H.; Fox, J. L.; Duarte, F. J. (1988). "Lasing characteristics of new-coumarin-analog dyes: broadband and narrow-linewidth performance". Appl. Opt. 27 (3): 443–445. Bibcode:1988ApOpt..27..443C. doi:10.1364/ao.27.000443. PMID 20523615.
  18. ^ Duarte, F. J.; Liao, L. S.; Vaeth, K. M.; Miller, A. M. (2006). "Widely tunable laser emission using the coumarin 545 tetramethyl dye as gain medium". J. Opt. A. 8 (2): 172–174. Bibcode:2006JOptA...8..172D. doi:10.1088/1464-4258/8/2/010.
  19. ^ Duarte, F. J.; Liao, L. S.; Vaeth, K. M. (2005). "Coherence characteristics of electrically excited tandem organic light-emitting diodes". Opt. Lett. 30 (22): 3072–3074. Bibcode:2005OptL...30.3072D. doi:10.1364/ol.30.003072. PMID 16315725.
  20. ^ US 4175982, Loutfy et al., issued Nov. 27, 1978, assigned to Xerox Corp 
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