3β-acetoxy-6-nitro-Δ5-androst-5-en-17-one | 31559-86-1

• 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: 3β-acetoxy-6-nitro-Δ5-androst-5-en-17-one
• 英文别名: 3β-acetoxy-6-nitroandrost-5-en-17-one；3β-acetoxy-6-nitroandrosten-17-one；3β-Hydroxy-6-nitro-androsten-(5)-on-(17)-acetat；3β-Acetoxy-6-nitro-androst-5-en-17-on；3Beta-acetoxy-6-nitroandrost-5-en-17-one；[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-6-nitro-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 31559-86-1
• 化学式: C₂₁H₂₉NO₅
• 分子量: 375.465
• InChiKey: QKVQVEKOCYORMD-AVZJEMISSA-N

物化性质

• 熔点：
  219 °C(Solv: ethyl ether (60-29-7); ethyl acetate (141-78-6))
• 沸点：
  501.1±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-6-nitro-Δ5-androst-5-en-17-one 在 水 、 magnesium 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以92%的产率得到3β-acetoxyandrostane-6,17-dione
  参考文献：
  名称：

  Das, Nalin B.; Sarangi, Chintamani; Nanda, Bhagabat, Journal of Chemical Research - Part S, 1996, # 1, p. 28 - 29

  摘要：

  DOI：
• 作为产物：
  描述：

  醋酸去氢表雄酮 在 吡啶 、 亚硝酰氯 作用下， 以 四氯化碳 为溶剂， 生成 3β-acetoxy-6-nitro-Δ5-androst-5-en-17-one
  参考文献：
  名称：

  类固醇系列。九。获得6-硝基类固醇衍生物的新途径。

  摘要：

  胆固醇乙酸酯（Ia）、雄甾-5-烯-3β,17β-二醇二乙酸酯（Ib）以及3β-羟基雄甾-5-烯-17-酮乙酸酯（Ic）与亚硝酰氯反应，以高产率得到了相应的5α-氯-6β-硝基化合物。该加合物在碱性条件下可直接转化为Δ5-6-硝基化合物，并可转化为Δ4-3-氧代-6α-硝基甾体衍生物。

  DOI：

  10.1248/cpb.10.1177

文献信息

• Tin(<scp>II</scp>) chloride dihydrate–a mild reagent for the transformation of 6-nitro-Δ⁵-steroids to 5α-hydroxy-6-ketosteroids
  作者：Gireesh M. Singhal、Nalin B. Das、Ram P. Sharma

  DOI：10.1039/c39900000498

  日期：——

  Reaction of excess hydrated tin(II) chloride with 6-nitro-Δ5-steroids (1a–g) and (5) in tetrahydrofuran furnishes 5α-hydroxy-6-ketosteroids (2a–g) and (6) respectively, in good yields.

  过量水合氯化亚锡与6-硝基-Δ5-甾体（1a-g）及（5）在四氢呋喃中的反应，分别以良好产率得到5α-羟基-6-酮甾体（2a-g）及（6）。
• INHIBITORS OF CYP17A1
  申请人：University of Kansas

  公开号：US20160031929A1

  公开（公告）日：2016-02-04

  Compounds according to formula I or II are provided. Such compounds are useful in treating cancers, such as leukemia, colon cancer, breast cancer, or prostate cancer by beneficially inhibiting CYP17A1. Pharmaceutical compositions and methods including the compounds are also provided.

  根据公式I或II提供了化合物。这些化合物对治疗白血病、结肠癌、乳腺癌或前列腺癌等癌症具有用处，通过有益地抑制CYP17A1。还提供了包括这些化合物的药物组合物和方法。
• The effects of DHEA, 3β-hydroxy-5α-androstane-6,17-dione, and 7-amino-DHEA analogues on short term and long term memory in the mouse
  作者：Marc-Antoine Bazin、Laïla El Kihel、Michel Boulouard、Valentine Bouët、Sylvain Rault

  DOI：10.1016/j.steroids.2009.06.010

  日期：2009.11

  Neurosteroids have been reported to modulate memory processes in rodents. Three analogues of dehydroepiandrosterone (DHEA), two of them previously described (7 beta-aminoDHEA and 7 beta-amino-17-ethylenedioxy-DHEA), and a new one (3 beta-hydroxy-5 alpha-androstane-6,17-dione) were synthesized, and their effects were evaluated on memory. This study examined their effects on long term and short term memory in male (6 weeks old) NMRI mice in comparison with the reference drug. Long term memory was assessed using the passive avoidance task and short term memory (spatial working memory) using the spontaneous alternation task in a Y maze. Moreover, the effects of DHEA and its analogues on spontaneous locomotion were measured. In all tests, DHEA and analogues were injected at three equimolar doses (0.300-1.350-6.075 mu M/kg). DHEA and its three analogues administered immediately post-training at the highest doses (6.075 mu M/kg, s.c.) improved retention in passive avoidance test. Without effect per se in the spatial working memory task, the four compounds failed to reverse scopolamine (1 mg/kg, i.p.)-induced deficit in spontaneous alternation. These data suggested an action of DHEA and analogues in consolidation of long term memory particularly when emotional components are implied. Moreover, data indicated that pharmacological modulation of DHEA as performed in this study provides derivatives giving the same mnemonic profile than reference molecule. Published by Elsevier Inc.
• A rearrangement in the nitration of 3β, 17β-diacetoxy-7-norandrost-5-ene
  作者：James R. Hanson、Peter B. Hitchcock、Revathy Manickavasagar

  DOI：10.1039/p19940002073

  日期：——

  The nitration of 3 beta,17 beta-diacetoxy-7-norandrost-5-ene by fuming nitric acid leads to 3 beta,17 beta-diacetoxy-5 beta-nitroxy-6 alpha-nitro-7-norandrostane and to the rearrangement product 2. A number of minor products were also identified. The formation of these can be rationalized in terms of a Markownikoff directed diaxial (5 beta,6 alpha) addition to the Delta(5)-double bond of the B-norsteroid which contrasts with the 5 alpha,6 beta-diaxial addition found in the normal steroids.
• SINGHAL, GIREESH M.;DAS, NALIN B.;SHARMA, RAM P., J. CHEM. SOC. CHEM. COMMUN.,(1990) N, C. 498-499
  作者：SINGHAL, GIREESH M.、DAS, NALIN B.、SHARMA, RAM P.

  DOI：——

  日期：——