Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

Dienolone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Dienolone
Clinical data
Other namesRU-3118; Nordienolone, Dehydronandrolone.
ATC code
  • None
Identifiers
  • (8S,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.125.823Edit this at Wikidata
Chemical and physical data
FormulaC18H24O2
Molar mass272.388 g·mol−1
3D model (JSmol)
  • CC12CCC3=C4CCC(=O)C=C4CCC3C1CCC2O
  • InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,15-17,20H,2-9H2,1H3/t15-,16+,17+,18+/m1/s1
  • Key:PUQSDJZESAQGQS-OWSLCNJRSA-N

Dienolone (developmental code nameRU-3118; online product namesTrenazone,[1]Dienazone), ornordienolone, also known as19-nor-δ9(10)-testosterone,δ9(10)-nandrolone, orestra-4,9(10)-dien-17β-ol-3-one, is asyntheticanabolic-androgenic steroid (AAS) of the19-nortestosterone group that was never marketed.[2] It has been found to possess slightly loweraffinity for theandrogen receptor (AR) andprogesterone receptor (PR) relative tonandrolone inrat andrabbittissuebioassays, whereas trenbolone was found to possess the same affinity for the AR as dienolone but several-fold increased affinity for the PR.[3]Dienedione (the 17-ketoanalogue of dienolone, also known as 19-nor-4,9-androstadienedione) is thought to be aprohormone of dienolone,[4] whilemethyldienolone andethyldienolone areorally active17α-alkylated AAS derivatives of dienolone.[5][6] In contrast,dienogest, the 17α-cyanomethyl derivative of dienolone, is a potentprogestogen andantiandrogen.[7]

Chemistry

[edit]

Synthesis

[edit]
Polyvinylpyridine

Prenortestosterone [1089-78-7][8] (see undernandrolone synthesis) can be brominated. 2xdehydrohalogenation step then leads to dienolone.[9][10]In the old method a mixture of molecular bromine and pyridine had been used as the reagents. However, in the new and improved synthesis the reagent was changed to poly(vinylpyridine) bromide perbromide (P(4-VPBPB)) [91650-35-0],[11] polyvinyl(pyridine) (PVP orP4VP) [25232-41-1] and pyridine. This gives an improved yield of product

Application

[edit]

WhilstDienedione can be used as a precursor totrenbolone, it is also fully possible to employ Dienolone (Dehydronandrolone), as was recently claimed.[12][13][14]

The synthesis of11β-methyl-19-nortestosterone is an additional use of dienolone.

See also

[edit]

References

[edit]
  1. ^Waller CC, McLeod MD (December 2014). "A simple method for the small scale synthesis and solid-phase extraction purification of steroid sulfates".Steroids.92:74–80.doi:10.1016/j.steroids.2014.09.006.hdl:1885/15429.PMID 25286236.S2CID 11504510.
  2. ^"STATUS DECISION OF CONTROLLED AND NON-CONTROLLED SUBSTANCE(S)"(PDF). August 12, 2011. RetrievedApril 29, 2025.
  3. ^Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors".Journal of Steroid Biochemistry.27 (1–3):255–269.doi:10.1016/0022-4731(87)90317-7.PMID 3695484.
  4. ^"2009 - Final Rule: Classification of Three Steroids as Schedule III Anabolic Steroids Under the Controlled Substances Act". Archived fromthe original on January 8, 2010.
  5. ^Thevis M, Schanzer W (18 December 2009)."Synthetic Anabolic Agents: Steroids and Nonsteroidal Selective Androgen Receptor Modulators". In Thieme D, Hemmersbach P (eds.).Doping in Sports. Springer Science & Business Media. pp. 103, 157,162–164.ISBN 978-3-540-79088-4.
  6. ^Potts GO, Arnold A, Beyler AL (6 December 2012)."Dissociation of the androgenic and other hormonal activities from the protein anabolic effects of steroids". In Kochakian CD (ed.).Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 380–381.doi:10.1007/978-3-642-66353-6_11.ISBN 978-3-642-66353-6.
  7. ^Foster RH, Wilde MI (November 1998). "Dienogest".Drugs.56 (5):825–33, discussion 834–5.doi:10.2165/00003495-199856050-00007.PMID 9829156.S2CID 262326901.
  8. ^Patrick J. Bednarski, et al.U.S. patent 4,745,109 (1988 to Washington Research Foundation).
  9. ^Menzenbach, B.; Hübner, M. (October 1986)."Synthese von 3‐Keto‐4,9‐diensteroiden mit polymeren Reagenzien".Zeitschrift für Chemie.26 (10):371–371.doi:10.1002/zfch.19860261007.
  10. ^Muddana, S. S.; Price, A. M.; MacBride, M. M.; Peterson, B. R. (1 October 2004)."11β-Alkyl-Δ 9 -19-Nortestosterone Derivatives: High-Affinity Ligands and Potent Partial Agonists of the Androgen Receptor".Journal of Medicinal Chemistry.47 (21):4985–4988.doi:10.1021/jm0342515.
  11. ^Wood WF (2001)."Poly(4-vinylpyridinium bromide perbromide)".Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons.doi:10.1002/047084289X.rp188.
  12. ^Anna Rencurosi, WO2022106574 (to Fabbrica Italiana Sintetici SpA (FIS)).
  13. ^Anna Rencurosi & Roberto Brescello, WO2022106566 (to Fabbrica Italiana Sintetici SpA (FIS)).
  14. ^张峥斌, et al. CN117659109 (2024 to Inner Mongolia Junye Biological Pharmaceutical Co ltd, Jiangxi Junye Biological Pharmaceutical Co ltd, Zhejiang Xianju Junye Pharmaceutical Co ltd).
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
Retrieved from "https://en.wikipedia.org/w/index.php?title=Dienolone&oldid=1337285844"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2026 Movatter.jp