Coumestan
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Names | |
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IUPAC name
Pterocarp-6a(11a)-en-6-one
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Systematic IUPAC name
6H-[1]Benzofuro[3,2-c][1]benzopyran-6-one | |
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3D model (JSmol)
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ChEBI | |
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PubChemCID
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UNII | |
CompTox Dashboard(EPA)
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Properties | |
C15H8O3 | |
Molar mass | 236.22 g/mol |
Melting point | 187 to 188 °C (369 to 370 °F; 460 to 461 K)[1] |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Coumestanis aheterocyclicorganic compound.Coumestan forms the central core of a variety of natural compounds known collectively as coumestans. Coumestans are oxidation products ofpterocarpan[2]that are similar tocoumarin.Coumestans, includingcoumestrol,aphytoestrogen,are found in a variety of plants. Food sources high in coumestans includesplit peas,pinto beans,lima beans,and especiallyalfalfaandcloversprouts.[3]
Coumestrolhas about the same binding affinity for theER-βestrogen receptoras17β-estradiol,but much less affinity than17α-estradiol,although the estrogenic potency of coumestrol at both receptors is much less than that of 17β-estradiol.[4]
Because of the estrogenic activity of some coumestans, a variety ofsyntheseshave been developed that allow the preparation of coumestans so that their pharmacological effects can be explored.[5][6]
Coumestans
[edit]References
[edit]- ^Singh, Rishi Pal; Singh, Daljeet (1985)."An elegant synthesis of 6H-benzofuro[3,2-c][1]benzopyran-6-ones".Heterocycles.23(4): 903.doi:10.3987/R-1985-04-0903.
- ^V. A. Tuskaev (April 2013). "Synthesis and biological activity of coumestan derivatives (Review)".Pharmaceutical Chemistry Journal.47(1): 1–11.doi:10.1007/s11094-013-0886-5.S2CID32550281.
- ^Barbour S. Warren; Carol Devine (July 2001)."Phytoestrogens and Breast Cancer".Program on Breast Cancer and Environmental Risk Factors.Cornell University.Retrieved2011-03-19.
- ^Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA (1998)."Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta".Endocrinology.139(10): 4252–4263.doi:10.1210/endo.139.10.6216.PMID9751507.
- ^Yao, Tuanli; Yue, Dawei; Larock, Richard C (2005). "An Efficient Synthesis of Coumestrol and Coumestans by Iodocyclization and Pd-Catalyzed Intramolecular Lactonization".Journal of Organic Chemistry.70(24): 9985–9989.doi:10.1021/jo0517038.PMID16292831.
- ^Takeda, Norihiko; Miyata, Okiko; Naito, Takeaki (2007). "Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: short synthesis of natural 2-arylbenzofurans".European Journal of Organic Chemistry.2007(9): 1491–1509.doi:10.1002/ejoc.200601001.