Bisdehydrodoisynolic acid

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Bisdehydrodoisynolic acid
Bisdehydrodoisynolic acid.svg
Identifiers
Chemical and physical data
Formula C18H20O3
Molar mass 284.36 g·mol−1
3D model (JSmol)

Bisdehydrodoisynolic acid (BDDA), as the (Z)-isomer ((Z)-BDDA), is a synthetic, nonsteroidal estrogen related to doisynolic acid that was never marketed.[1] It is one of the most potent estrogens known,[2][3] although it has more recently been characterized as a selective estrogen receptor modulator (SERM).[3][4] BDDA and other doisynolic acid derivatives display relatively low affinity accompanied by disproportionately high estrogenic potency in vivo,[5] which was eventually determined to be due to transformation into metabolites with greater estrogenic activity.[4] The drug was discovered in 1947 as a degradation product of the reaction of equilenin or dihydroequilenin with potassium hydroxide.[6] It is the seco-analogue of equilenin, while doisynolic acid is the seco-analogue of estrone.[7] These compounds, along with diethylstilbestrol, can be considered to be open-ring analogues of estradiol.[8] The methyl ether of BDDA, doisynoestrol, is also an estrogen, and in contrast to BDDA, has been marketed.[2][9]

See also[edit]

References[edit]

  1. ^ The Effects of (+)-Z-bisdehydrodoisynolic Acid on Diabetic Phenotype in Female Obese Zucker Rats. ProQuest. 2007. pp. 17–. ISBN 978-0-549-22172-2. 
  2. ^ a b Johnson, William S.; Graber, Robert P. (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. ISSN 0002-7863. 
  3. ^ a b Robert T. Blickenstaff; Anil C. Ghosh; Gordon C. Wolf (22 October 2013). Total Synthesis of Steroids: Organic Chemistry: A Series of Monographs. Elsevier Science. pp. 63–. ISBN 978-1-4832-1642-3. 
  4. ^ a b Adler, Molly; Hou, Yuqing; Sandrock, Paul; Meyers, Cal Y.; Winters, Todd A.; Banz, William J.; Adler, Stuart (2006). "Derivatives ofZ-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. ISSN 0013-7227. PMID 16709609. 
  5. ^ Banz, W.; Winters, T.; Hou, Y.; Adler, S.; Meyers, C. (2007). "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. ISSN 0018-5043. 
  6. ^ Gregory Pincus; Thimann Kenneth Vivian Pincus Gregory (2 December 2012). The Hormones V1: Physiology, Chemistry and Applications. Elsevier. pp. 364–366. ISBN 978-0-323-14206-9. 
  7. ^ Journal of Scientific & Industrial Research. Council of Scientific & Industrial Research. 1984. p. 213. 
  8. ^ Camille Georges Wermuth (2 May 2011). The Practice of Medicinal Chemistry. Academic Press. pp. 344–. ISBN 978-0-08-056877-5. 
  9. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 465–. ISBN 978-1-4757-2085-3.