Coumarin derivatives

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Chemical structure of coumarin Coumarine nu.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. Whereas, coumarin-pyridine hybrids have been prepared from the Knoevenagel condensation of pyridylacetontriles with substituted salicylaldehydes. [2]

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. [8] 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] [9] In basic research, preliminary evidence exists for coumarin having various biological activities, including anti-inflammatory, anti-tumor, antibacterial, and antifungal properties, among others. [8]

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. [10] [11] [12] It may be used to prevent recurrent blood clot formation from atrial fibrillation, thrombotic stroke, and transient ischemic attacks. [12]

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. [10] [13] Both coumarin and 1,3-indandione derivatives produce a uricosuric effect, presumably by interfering with the renal tubular reabsorption of urate. [14]

Laser dyes

Arising from tunable intramolecular charge transfer (ICT) properties within the molecule, coumarins have found purpose as dyes and stains, particularly those featuring electron-donating substituents at the 7-position, which can be used to enhance this behavior. Coumarin dyes are extensively used as gain media in blue-green tunable organic dye lasers. [15] [16] [17] Among the various coumarin laser dyes are coumarins 480, 490, 504, 521, 504T, and 521T. [17] Coumarin tetramethyl laser dyes offer wide tunability and high laser gain, [18] [19] and they are also used as active medium in coherent OLED emitters. [20] [15] [16] [17] and as a sensitizer in older photovoltaic technologies. [21]

References

  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. ↑ Burden, Thomas J.; Fernandez, Kathryn P. R.; Kagoro, Mary; Eastwood, Jonathan B.; Tanner, Theo F. N.; Whitwood, Adrian C.; Clark, Ian P.; Towrie, Michael; Krieger, Jean-Philippe; Lynam, Jason M.; Fairlamb, Ian J. S. (2023). "Coumarin C−H Functionalization by Mn(I) Carbonyls: Mechanistic Insight by Ultra-Fast IR Spectroscopic Analysis". Chemistry – A European Journal. 29 (25) e202203038. doi:10.1002/chem.202203038. ISSN   1521-3765. PMC   10947090 . PMID   36625067.
  3. ↑ International Programme on Chemical Safety. "Brodifacoum (pesticide data sheet)". Archived from the original on 2006-12-09. Retrieved 2006-12-14.
  4. ↑ 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.
  5. ↑ International Programme on Chemical Safety. "Bromadiolone (pesticide data sheet)". Archived from the original on 2006-12-21. Retrieved 2006-12-14.
  6. ↑ International Programme on Chemical Safety. "Difenacoum (health and safety guide)" . Retrieved 2006-12-14.
  7. ↑ 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.
  8. 1 2 3 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.
  9. ↑ 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.
  10. 1 2 "Coumarin". PubChem, National Library of Medicine, US National Institutes of Health. 4 April 2019. Retrieved 13 April 2019.
  11. ↑ "Coumarins and indandiones". Drugs.com. 2016. Retrieved 24 December 2016.
  12. 1 2 "Warfarin". Drugs.com. 7 March 2019. Retrieved 13 April 2019.
  13. ↑ 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.
  14. ↑ 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.
  15. 1 2 Schäfer, F. P., ed. (1990). Dye Lasers (3rd ed.). Berlin: Springer-Verlag.[ ISBN missing ]
  16. 1 2 Duarte, F. J.; Hillman, L. W., eds. (1990). Dye Laser Principles. New York: Academic.[ ISBN missing ]
  17. 1 2 3 Duarte, F. J. (2003). "Appendix of Laser Dyes". Tunable Laser Optics. New York: Elsevier-Academic.[ ISBN missing ]
  18. ↑ 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.
  19. ↑ 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.
  20. ↑ 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.
  21. ↑ US 4175982,Loutfy et al.,issued Nov. 27, 1978, assigned to Xerox Corp
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