7β-hydroxyandrost-5-ene-3,17-dione 3,17-diethylene diketal | 202415-48-3

• 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: 7β-hydroxyandrost-5-ene-3,17-dione 3,17-diethylene diketal
• 英文别名: 3,3,17,17-diethylenedioxy-7β-hydroxyandrost-5-ene
• CAS: 202415-48-3
• 化学式: C₂₃H₃₄O₅
• 分子量: 390.52
• InChiKey: XPPSGMMFJFOCFW-OLGWUGKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7β-hydroxyandrost-5-ene-3,17-dione 3,17-diethylene diketal 在 cerium(III) chloride 、 sodium iodide 作用下， 生成 4,6-雄烯二醇-3,17-二酮
  参考文献：
  名称：

  Synthesis of Some Novel 3,3-Ethylenedioxyandrost-7β-Acyloxy-5-Ene-17-One Derivatives as Potent Aromatase Inhibitors

  摘要：

  3,3,17,17-二亚乙基二氧基雄甾-5-烯由雄烯二酮酮化而得，雄烯二酮与 PDC 和 t-BuOOH 氧化生成 3,3,17,17-二亚乙基二氧基雄甾-5-烯-7-酮。在 CeCl3.6H2O 的存在下，NaBH4 对 3,3,17,17-二亚乙二氧基雄-5-烯-7-酮进行立体选择性还原，得到 3,3,17,17-二亚乙二氧基-7β-羟基雄-5-烯，用对甲苯磺酸对其进行脱保护，得到 3,3-亚乙二氧基雄-5-烯-7β-羟基和雄-4,6-二烯-3,17-二酮。通过酯化反应，从 3,3-亚乙二氧基雄-5-烯-7β-羟基得到了一系列雄烯二酮衍生物。通过质谱、1H NMR、13C NMR 和 HRMS 确认了它们的结构。

  DOI：

  10.3184/174751911x13129058638242
• 作为产物：
  描述：

  雄烯二酮 在 3,5-二甲基吡唑 、 chromium(VI) oxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 38.75h， 生成 7β-hydroxyandrost-5-ene-3,17-dione 3,17-diethylene diketal
  参考文献：
  名称：

  对连续甾醇合成的研究：甾体 A、B 环系统的功能化

  摘要：

  摘要雄甾烷-3α,4β,6α,7β-tetrol-17-one (2) 是制备 contignasterol (1) 的潜在关键中间体，其合成是通过 A,B 环部分的功能化实现的。容易获得的 androst-4-ene-3,17-dione (3)。

  DOI：

  10.1081/scc-120012989

文献信息

• C19-Steroids as androgen receptor modulators: Design, discovery, and structure-activity relationship of new steroidal androgen receptor antagonists
  作者：Padma Marwah、Ashok Marwah、Henry A. Lardy、Hiroshi Miyamoto、Chawnshang Chang

  DOI：10.1016/j.bmc.2006.05.022

  日期：2006.9

  Dehydroepiandrosterone (DHEA), the most abundant steroid in human circulating blood, is metabolized to sex hormones and other C-19-steroids. Our previous collaborative study demonstrated that androst-5-ene-3 beta,17 beta-diol (Adiol) and androst-4-ene-3,17-dione (Adione), metabolites of DHEA, can activate androgen receptor (AR) target genes. Adiol is maintained at a high concentration in prostate cancer tissue; even after androgen deprivation therapy and its androgen activity is not inhibited by the antiandrogens currently used to treat prostate cancer patients. We have synthesized possible metabolites of DHEA and several synthetic analogues and evaluated their role in androgen receptor transactivation to identify AR modulators. Steroids with low androgenic potential in PC-3 cell lines were evaluated for anti-dihydrotestosterone (DHT) and anti-Adiol activity. We discovered three potent antiandrogens: 3 beta-acetoxyandrosta-1,5-diene-17-one 17-ethylene ketal (ADEK), androsta-1,4-diene-3,17-dione 17-ethylene ketal (OAK), and 3 beta-hydroxyandrosta-5,16-diene (HAD) that antagonized the effects of DHT as well as of Adiol on the growth of LNCaP cells and on the expression of prostate-specific antigen (PSA). In vivo tests of these compounds will reveal their potential as potent antiandrogens for the treatment of prostate cancer. (c) 2006 Elsevier Ltd. All rights reserved.
• STUDIES TOWARD THE SYNTHESIS OF CONTIGNASTEROL: FUNCTIONALIZATION OF THE STEROIDAL A,B RING SYSTEM
  作者：Christine Rogers、Yaping Shen、David Burgoyne、Edward Piers

  DOI：10.1081/scc-120012989

  日期：2002.1

  ABSTRACT The synthesis of androstane-3α,4β,6α,7β-tetrol-17-one (2), a potentially key intermediate for the preparation of contignasterol (1), was achieved by functionalization of the A,B-ring portion of the readily available androst-4-ene-3,17-dione (3).

  摘要雄甾烷-3α,4β,6α,7β-tetrol-17-one (2) 是制备 contignasterol (1) 的潜在关键中间体，其合成是通过 A,B 环部分的功能化实现的。容易获得的 androst-4-ene-3,17-dione (3)。
• Synthesis of Some Novel 3,3-Ethylenedioxyandrost-7β-Acyloxy-5-Ene-17-One Derivatives as Potent Aromatase Inhibitors
  作者：Shao-Rui Chen、Dong-Zhi Liu

  DOI：10.3184/174751911x13129058638242

  日期：2011.8

  3,3,17,17-Diethylenedioxyandrost-5-ene was obtained by ketalisation of androstenedione, which was oxidised with PDC and t-BuOOH to form 3,3,17,17-diethylene-dioxyandrost-5-ene-7-one. Stereoselective reduction of 3,3,17,17-diethylene-dioxyandrost-5-ene-7-one by NaBH₄ in the presence of CeCl₃.6H₂O gave 3,3,17,17-diethylenedioxy-7β-hydroxy-androst-5-ene, which was deprotected with p-toluenesulfonic acid to gave 3,3-ethylenedioxyandrost-5-ene-7β-hydroxy and androst-4,6-dien-3,17-dione. A series of androstenedione derivatives were obtained from 3,3-ethylenedioxyandrost-5-ene-7β-hydroxy by the esterification reaction. Their structures were confirmed by MS, ¹H NMR, ¹³C NMR and HRMS.

  3,3,17,17-二亚乙基二氧基雄甾-5-烯由雄烯二酮酮化而得，雄烯二酮与 PDC 和 t-BuOOH 氧化生成 3,3,17,17-二亚乙基二氧基雄甾-5-烯-7-酮。在 CeCl3.6H2O 的存在下，NaBH4 对 3,3,17,17-二亚乙二氧基雄-5-烯-7-酮进行立体选择性还原，得到 3,3,17,17-二亚乙二氧基-7β-羟基雄-5-烯，用对甲苯磺酸对其进行脱保护，得到 3,3-亚乙二氧基雄-5-烯-7β-羟基和雄-4,6-二烯-3,17-二酮。通过酯化反应，从 3,3-亚乙二氧基雄-5-烯-7β-羟基得到了一系列雄烯二酮衍生物。通过质谱、1H NMR、13C NMR 和 HRMS 确认了它们的结构。