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Coumarin derivatives

March 15, 2024

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

Chemical structure of coumarin

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 edit

Medicine edit

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 edit

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 edit

  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. Annual Reviews. 71 (1): 631–658. doi:10.1146/annurev-arplant-081519-035634. ISSN 1543-5008. PMID 32176525. S2CID 212740956.
  2. ^ International Programme on Chemical Safety. . 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. . 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 

March 15, 2024
coumarin, derivatives, coumarins, redirects, here, class, anticoagulants, rodenticides, specifically, hydroxycoumarins, parent, compound, coumarin, derivatives, coumarin, considered, phenylpropanoids, among, most, important, derivatives, hydroxycoumarins, whic. Coumarins redirects here For the class of anticoagulants and rodenticides specifically see 4 Hydroxycoumarins For the parent compound see 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 Chemical structure of coumarinSome 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 Contents 1 Uses 1 1 Medicine 1 2 Laser dyes 2 ReferencesUses editMedicine edit 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 edit 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 edit 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 Annual Reviews 71 1 631 658 doi 10 1146 annurev arplant 081519 035634 ISSN 1543 5008 PMID 32176525 S2CID 212740956 International Programme on Chemical Safety Brodifacoum pesticide data sheet Archived from the original on 2006 12 09 Retrieved 2006 12 14 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 International Programme on Chemical Safety Bromadiolone pesticide data sheet Archived from the original on 2006 12 21 Retrieved 2006 12 14 International Programme on Chemical Safety Difenacoum health and safety guide Retrieved 2006 12 14 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 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 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 a b Coumarin PubChem National Library of Medicine US National Institutes of Health 4 April 2019 Retrieved 13 April 2019 Coumarins and indandiones Drugs com 2016 Retrieved 24 December 2016 a b Warfarin Drugs com 7 March 2019 Retrieved 13 April 2019 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 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 a b Schafer F P ed 1990 Dye Lasers 3rd ed Berlin Springer Verlag ISBN missing a b Duarte F J Hillman L W eds 1990 Dye Laser Principles New York Academic ISBN missing a b c Duarte F J 2003 Appendix of Laser Dyes Tunable Laser Optics New York Elsevier Academic ISBN missing 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 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 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 US 4175982 Loutfy et al issued Nov 27 1978 assigned to Xerox Corp Retrieved from https en wikipedia org w index php title Coumarin derivatives amp 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