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Bisdehydrodoisynolic acid

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Bisdehydrodoisynolic acid
Identifiers
  • 1-Ethyl-7-hydroxy-2-methyl-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid
PubChemCID
UNII
Chemical and physical data
FormulaC18H20O3
Molar mass284.355g·mol−1
3D model (JSmol)
  • CCC1C2=C(CCC1(C)C(O)=O)C1=CC=C(O)C=C1C=C2
  • InChI=1/C18H20O3/c1-3-16-15-6-4-11-10-12(19)5-7-13(11)14(15)8-9-18(16,2)17(20)21/h4-7,10,16,19H,3,8-9H2,1-2H3,(H,20,21)
  • Key:HMYBVYBHZVQZNH-UHFFFAOYNA-N

Bisdehydrodoisynolic acid(BDDA), as the (Z)-isomer ((Z)-BDDA), is asynthetic,nonsteroidalestrogenrelated todoisynolic acidthat was never marketed.[1]It is one of the most potent estrogens known,[2][3]although it has more recently been characterized as aselective estrogen receptor modulator(SERM).[3][4]BDDA and other doisynolic acid derivatives display relatively lowaffinityaccompanied by disproportionately high estrogenicpotencyin vivo,[5]which was eventually determined to be due to transformation intometaboliteswith greater estrogenic activity.[4]The drug was discovered in 1947 as a degradation product of the reaction ofequileninordihydroequileninwithpotassium hydroxide.[6]It is the seco-analogue of equilenin, while doisynolic acid is the seco-analogue ofestrone.[7]These compounds, along withdiethylstilbestrol,can be considered to be open-ring analogues ofestradiol.[8]Themethyletherof BDDA,doisynoestrol,is also an estrogen, and in contrast to BDDA, has been marketed.[2][9]

See also

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References

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  1. ^Banz W, Strader A, Ajuwon K, Ortiz L, James B, Higginbotham DA, Hou Y, Meyers C (May 2007)."The Effects of (+)-Z-bisdehydrodoisynolic Acid on Diabetic Phenotype in Female Obese Zucker Rats".Experimental Biology.pp. 17–.ISBN978-0-549-22172-2.[permanent dead link]
  2. ^abJohnson WS, Graber RP (1950). "The Stobbe Condensation with 6-Methoxy-2-propionylnaphthalene. A Synthesis of Bisdehydrodoisynolic Acid1".Journal of the American Chemical Society.72(2): 925–935.doi:10.1021/ja01158a075.ISSN0002-7863.
  3. ^abBlickenstaff RT, Ghosh AC, Wolf GC (22 October 2013).Total Synthesis of Steroids: Organic Chemistry: A Series of Monographs.Elsevier Science. pp. 63–.ISBN978-1-4832-1642-3.
  4. ^abAdler M, Hou Y, Sandrock P, Meyers CY, Winters TA, Banz WJ, Adler S (August 2006)."Derivatives of Z-bisdehydrodoisynolic acid provide a new description of the binding-activity paradox and selective estrogen receptor modulator activity".Endocrinology.147(8): 3952–3960.doi:10.1210/en.2006-0316.PMID16709609.
  5. ^Banz WJ, Winters TA, Hou Y, Adler S, Meyers CY (December 1998). "Comparative effects of the selective estrogen receptor modulators (-)-, (+)- and (+/-)-Z bisdehydrodoisynolic acids on metabolic and reproductive parameters in male and female rats".Hormone and Metabolic Research.30(12): 730–736.doi:10.1055/s-2007-978968.PMID9930631.
  6. ^Pincus G, Thimann KV (2 December 2012).The Hormones V1: Physiology, Chemistry and Applications.Elsevier. pp. 364–366.ISBN978-0-323-14206-9.
  7. ^Journal of Scientific & Industrial Research.Council of Scientific & Industrial Research. 1984. p. 213.
  8. ^Morice C,Wermuth CG (2 May 2011)."Ring transformations".In Wermuth CG (ed.).The Practice of Medicinal Chemistry.Academic Press. pp. 343-362 (344).ISBN978-0-08-056877-5.
  9. ^Elks J (14 November 2014)."Doisynoestrol".The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies.Springer. pp. 465–.ISBN978-1-4757-2085-3.
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