| 词条 | Bisdehydrodoisynolic acid |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = 1-Ethyl-7-hydroxy-2-methyl-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid | image = Bisdehydrodoisynolic acid.svg | width = 250 | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = | CAS_supplemental = | ATCvet = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = | UNII = | KEGG = | ChEBI = | ChEMBL = | C=18 | H=20 | O=3 | smiles = CCC1C2=C(CCC1(C)C(O)=O)C1=CC=C(O)C=C1C=C2 | StdInChI_Ref = | StdInChI = 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) | StdInChIKey_Ref = | StdInChIKey = HMYBVYBHZVQZNH-UHFFFAOYNA-N | synonyms = }}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][5] BDDA and other doisynolic acid derivatives display relatively low affinity accompanied by disproportionately high estrogenic potency in vivo,[4] which was eventually determined to be due to transformation into metabolites with greater estrogenic activity.[5] 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
References1. ^{{cite book|title=The Effects of (+)-Z-bisdehydrodoisynolic Acid on Diabetic Phenotype in Female Obese Zucker Rats|url=https://books.google.com/books?id=L3V0ypHV1H8C&pg=PA17|year=2007|publisher=ProQuest|isbn=978-0-549-22172-2|pages=17–}} {{Estrogen receptor modulators}}2. ^1 {{cite journal|last1=Johnson|first1=William S.|last2=Graber|first2=Robert P.|title=The Stobbe Condensation with 6-Methoxy-2-propionylnaphthalene. A Synthesis of Bisdehydrodoisynolic Acid1|journal=Journal of the American Chemical Society|volume=72|issue=2|year=1950|pages=925–935|issn=0002-7863|doi=10.1021/ja01158a075}} 3. ^1 {{cite book|author1=Robert T. Blickenstaff|author2=Anil C. Ghosh|author3=Gordon C. Wolf|title=Total Synthesis of Steroids: Organic Chemistry: A Series of Monographs|url=https://books.google.com/books?id=Vpb-BAAAQBAJ&pg=PA63|date=22 October 2013|publisher=Elsevier Science|isbn=978-1-4832-1642-3|pages=63–}} 4. ^{{cite journal|last1=Banz|first1=W.|last2=Winters|first2=T.|last3=Hou|first3=Y.|last4=Adler|first4=S.|last5=Meyers|first5=C.|title=Comparative Effects of the Selective Estrogen Receptor Modulators (-)-, (+)- and (±)-Z-Bisdehydrodoisynolic Acids on Metabolic and Reproductive Parameters in Male and Female Rats|journal=Hormone and Metabolic Research|volume=30|issue=12|year=2007|pages=730–736|issn=0018-5043|doi=10.1055/s-2007-978968}} 5. ^1 {{cite journal|last1=Adler|first1=Molly|last2=Hou|first2=Yuqing|last3=Sandrock|first3=Paul|last4=Meyers|first4=Cal Y.|last5=Winters|first5=Todd A.|last6=Banz|first6=William J.|last7=Adler|first7=Stuart|title=Derivatives ofZ-Bisdehydrodoisynolic Acid Provide a New Description of the Binding-Activity Paradox and Selective Estrogen Receptor Modulator Activity|journal=Endocrinology|volume=147|issue=8|year=2006|pages=3952–3960|issn=0013-7227|doi=10.1210/en.2006-0316|pmid=16709609}} 6. ^{{cite book|author1=Gregory Pincus|author2=Thimann Kenneth Vivian Pincus Gregory|title=The Hormones V1: Physiology, Chemistry and Applications|url=https://books.google.com/books?id=Thtz7On_lhEC&pg=PA364|date=2 December 2012|publisher=Elsevier|isbn=978-0-323-14206-9|pages=364–366}} 7. ^{{cite book|title=Journal of Scientific & Industrial Research|url=https://books.google.com/books?id=0Z0jAAAAMAAJ|year=1984|publisher=Council of Scientific & Industrial Research.|page=213}} 8. ^{{cite book|author=Camille Georges Wermuth|title=The Practice of Medicinal Chemistry|url=https://books.google.com/books?id=Qmt1_DQkCpEC&pg=PA344|date=2 May 2011|publisher=Academic Press|isbn=978-0-08-056877-5|pages=344–}} 9. ^{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA465|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=465–}} 3 : Carboxylic acids|Phenanthrenes|Synthetic estrogens |
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