Coumarin derivatives explained

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.[8] In basic research, preliminary evidence exists for coumarin having various biological activities, including anti-inflammatory, anti-tumor, antibacterial, and antifungal properties, among others.

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]

Notes and References

  1. Jacobowitz . Joseph R. . Weng . Jing-Ke . 2020-04-29 . Exploring Uncharted Territories of Plant Specialized Metabolism in the Postgenomic Era . . . 71 . 1 . 631–658 . 10.1146/annurev-arplant-081519-035634 . 1543-5008 . 32176525 . 212740956.
  2. Web site: International Programme on Chemical Safety . Brodifacoum (pesticide data sheet) . dead . https://web.archive.org/web/20061209133155/http://inchem.org/documents/pds/pds/pest57_e.htm . 2006-12-09 . 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 . 10.1056/NEJMcpc069032 . 17215536.
  4. Web site: International Programme on Chemical Safety . Bromadiolone (pesticide data sheet) . dead . https://web.archive.org/web/20061221043656/http://www.inchem.org/documents/pds/pds/pest88_e.htm . 2006-12-21 . 2006-12-14.
  5. Web site: International Programme on Chemical Safety . Difenacoum (health and safety guide) . 2006-12-14.
  6. Syah . Y. M. . etal . 2009 . A modified oligostilbenoid, diptoindonesin C, from Shorea pinanga Scheff . Natural Product Research . 23 . 7 . 591–594 . 10.1080/14786410600761235 . 19401910 . 20216115.
  7. Venugopala . K. N. . Rashmi . V . Odhav . B . 2013 . Review on Natural Coumarin Lead Compounds for Their Pharmacological Activity . BioMed Research International . 2013 . 1–14 . 10.1155/2013/963248 . 3622347 . 23586066 . free.
  8. Bye . A. . King . H. K. . 1970 . The biosynthesis of 4-hydroxycoumarin and dicoumarol by Aspergillus fumigatus Fresenius . Biochemical Journal . 117 . 2 . 237–45 . 10.1042/bj1170237 . 1178855 . 4192639.
  9. Web site: Coumarin . 4 April 2019 . PubChem, National Library of Medicine, US National Institutes of Health . 13 April 2019.
  10. Web site: Coumarins and indandiones . Drugs.com . 2016 . 24 December 2016.
  11. Web site: Warfarin . Drugs.com . 13 April 2019 . 7 March 2019.
  12. Farinola. N. . N. . Piller. Lymphatic Research and Biology. June 1, 2005. 3. 2. 81–86. 10.1089/lrb.2005.3.81. Pharmacogenomics: Its role in re-establishing coumarin as treatment for lymphedema. 16000056.
  13. 10.1111/j.0954-6820.1964.tb00594.x. 0954-6820. 175. 4. 461–468. Christensen. Flemming. Uricosuric Effect of Dicoumarol. Acta Medica Scandinavica. 1964-01-12. 14149651.
  14. Book: F. P. Schäfer. Schäfer. F. P.. Dye Lasers. 3rd. Berlin. Springer-Verlag. 1990.
  15. Book: F. J. Duarte. Duarte. F. J.. L. W.. Hillman. Dye Laser Principles. New York. Academic. 1990.
  16. Book: Duarte, F. J.. Tunable Laser Optics. New York. Elsevier-Academic. 2003. Appendix of Laser Dyes.
  17. Chen . C. H. . Fox . J. L. . Duarte . F. J. . Lasing characteristics of new-coumarin-analog dyes: broadband and narrow-linewidth performance . Appl. Opt. . 27 . 3 . 443–445 . 1988 . 10.1364/ao.27.000443. 20523615 . 1988ApOpt..27..443C .
  18. Duarte . F. J. . Liao . L. S. . Vaeth . K. M. . Miller . A. M. . Widely tunable laser emission using the coumarin 545 tetramethyl dye as gain medium . J. Opt. A . 8 . 2 . 172–174 . 2006 . 10.1088/1464-4258/8/2/010. 2006JOptA...8..172D .
  19. Duarte . F. J. . Liao . L. S. . Vaeth . K. M. . Coherence characteristics of electrically excited tandem organic light-emitting diodes . Opt. Lett. . 30 . 22 . 3072–3074 . 2005 . 10.1364/ol.30.003072 . 16315725. 2005OptL...30.3072D .
  20. US. 4175982. Loutfy et al.. Nov. 27, 1978. Xerox Corp.

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