11β-hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one | 17521-90-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 11β-hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one
• 英文别名: 11β-hydroxy-3-methoxy-estra-1,3,5(10)-trien-17-one；11β-Hydroxy-3-methoxy-oestra-1,3,5(10)-trien-17-on；(8S,9S,11S,13S,14S)-11-hydroxy-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 17521-90-3
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: ATNWIRRJSYPIJW-FYAJOAKPSA-N

物化性质

• 沸点：
  471.8±45.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11β-hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one 生成 11β-Chloroestrone 3-Methyl Ether
  参考文献：
  名称：

  CROWE, DAVID E.;TANABE, MASATO;PETERS, RICHARD

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-雄二烯-11-beta-醇-3,17-二酮 在 氢氧化钾 、 mineral oil 作用下， 生成 11β-hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  Preparation and Reactions of 11-Substituted 1,3,5(10)-Estratrienes.¹ I. 11-Oxygenated Estrones and Estradiols

  摘要：

  DOI：

  10.1021/ja01542a045

文献信息

• Stereochemistry of Steroids containing Aromatic A-Ring. II. Reaction of 9α, 11α-Epoxyestrone.
  作者：Hiroko Hasegawa、Shigeo Nozoe、Kyosuke Tsuda

  DOI：10.1248/cpb.11.1037

  日期：——

  The reduction of 3-hydroxy-9α, 11α-epoxyestra-1, 3, 5 (10)-trien-17-one (III) with lithium aluminum hydride gave estra-1, 3, 5 (10)-triene-3, 11α, 17β-triol. The reaction of III with hydrogen chloride in methanol yielded 3-hydroxy-9β-estra-1, 3, 5 (10)-triene-11, 17-dione (IXa). On the other hand, the reaction in chloroform afforded 9ξ-chloro-3, 11α-dihydroxyestra-1, 3, 5 (10)-trien-17-one (VIIIa). With alkali 3-hydroxyestra-1, 3, 5 (10)-triene-11, 17-dione (Va) is converted into 9β-isomer (IXa).

  3-羟基-9α,11α-环氧雌甾-1,3,5(10)-三烯-17-酮（III）与氢化铝锂反应生成雌甾-1,3,5(10)-三烯-3,11α,17β-三醇。III与甲醇中的氯化氢反应生成3-羟基-9β-雌甾-1,3,5(10)-三烯-11,17-二酮（IXa）。另一方面，在氯仿中的反应生成9ξ-氯-3,11α-二羟基雌甾-1,3,5(10)-三烯-17-酮（VIIIa）。在碱的作用下，3-羟基雌甾-1,3,5(10)-三烯-11,17-二酮（Va）转化为9β-异构体（IXa）。
• Synthesis of 11.beta.-[18F]Fluoro-5.alpha.-dihydrotestosterone and 11.beta.-[18F]Fluoro-19-nor-5.alpha.-dihydrotestosterone: Preparation via Halofluorination-Reduction, Receptor Binding, and Tissue Distribution
  作者：Yearn Seong Choe、Pelle J. Lidstroem、Dae Yoon Chi、Thomas A. Bonasera、Michael J. Welch、John A. Katzenellenbogen

  DOI：10.1021/jm00005a009

  日期：1995.3

  We have prepared 11 beta-fluoro-5 alpha-dihydrotestosterone (11 beta-F-DHT, 1) and 11 beta-fluoro-19-nor-5 alpha-dihydrotestosterone (11 beta-F-19-nor-DHT, 2) in order to investigate the properties of these new androgens labeled with fluorine-18 as potential androgen receptor (AR)-based imaging agents for prostate cancer. These compounds were synthesized in 6 steps from hydrocortisone and in 13 steps from 1,4-androstadiene-3,11,17-trione, respectively. Relative binding affinities (RBA) of 11 beta-F-DHT and 11 beta-F-19-nor-DHT to AR are 53.1 and 75.3 (R1881 = 100), respectively, the latter being the highest reported among fluorine-substituted androgens. The fluorination step, which involves addition of halogen fluoride across the 9(11)-double bond, followed by reductive dehalogenation at the 9 alpha-position has been adapted to introduce a fluorine-18-label at the 11 beta-position of DHT and 19-nor-DHT. The two high-affinity F-18-labeled ligands [F-18]-1 and [F-18]-2 were evaluated in vivo, in tissue distribution studies using diethylstilbestrol-pretreated mature male rats. 11 beta-F-DHT shows high prostate uptake and selective prostate to blood and prostate to muscle uptake ratios, the latter two ratios increasing from 5 and 8 at 1 h to 12 and 19 at 4 h postinjection. Moreover, this compound has low uptake in bone, displaying the lowest in vivo defluorination among all androgens labeled with fluorine-18 tested so far. The in vive properties of 11 beta-F-DHT in rats are thus favorable for imaging of prostate cancer. On the other hand, 11 beta-F-19-nor-DHT shows low prostate uptake with low selectivity and high uptake in liver, kidney, and bladder. Even though this ligand has the highest RBA and undergoes little metabolic defluorination, it appears to suffer from rapid metabolism in vivo. Therefore, it is apparent that the biodistribution properties of androgens are affected by their structure and metabolism as well as by their RBA.
• Estrone compounds
  申请人：UPJOHN CO

  公开号：US02874173A1

  公开（公告）日：1959-02-17
• CYCLIC HYDROCARBONS WITH AN AMINOALKYL SIDECHAIN
  申请人：THE UPJOHN COMPANY

  公开号：EP0356454B1

  公开（公告）日：1992-06-17
• US5001234A
  申请人：——

  公开号：US5001234A

  公开（公告）日：1991-03-19