1,4,6-雄甾三烯-3-酮-17beta-醇 | 4075-12-1

• 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
• 中文名称: 1,4,6-雄甾三烯-3-酮-17beta-醇
• 英文名称: 1,4,6-Androstatrien-17beta-ol-3-one
• 英文别名: 17β-hydroxyandrost-1,4,6-triene-3-one；17β-hydroxyandrosta-1,4,6-trien-3-one；3-oxo-1,4,6-androstatrien-17β-ol；17β-hydroxy-androsta-1,4,6-trien-3-one；17β-Hydroxy-androsta-1,4,6-trien-3-on；Androstatrien-(1,4,6)-on-(3)-ol-(17β)；1,4,6-Androstatrien-3-one-17beta-ol；(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-8,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one
• CAS: 4075-12-1
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: WGFQJPRCLLMHRT-DYKIIFRCSA-N

物化性质

• 溶解度：
  可溶于乙腈（少许）、氯仿（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4,6-雄甾三烯-3-酮-17beta-醇 生成 (1S,7S,8R,9S,10R,13S,14S,17S)-17-Hydroxy-1,7,10,13-tetramethyl-1,2,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  Antiprogestational agents. The synthesis of 7-alkyl steroidal ketones with anti-implantational and antidecidual activity

  摘要：

  A series of 7alpha- and 7beta- alkyl derivatives of steroidal 4-en- and 5-en-3-ones were prepared by 1,6-conjugate addition of organocopper reagents to various steroidal 4,6-dien-3-ones of the androstane, estrane and gonane series. Biological study of these and related compounds revealed that 17beta-hydroxy-7alpha-methyl-5-androsten-3-one (2), 17beta-hydroxy-7alpha-methyl-5-estren-3-one acetate and 17beta-hydroxy-7alpha-methyl-4-estren-3-one acetate had significant anti-implantational and antidecidual activities. The contragestative effects were associated with the latter anti-hormonal properties, and not with the androgenicity of these compounds.

  DOI：

  10.1016/0039-128x(76)90136-7
• 作为产物：
  描述：

  2α,6β-dibromo-17β-acetoxyandrost-3-en-3-one 在 2,4,6-三甲基吡啶 、 氢氧化钾 作用下， 生成 1,4,6-雄甾三烯-3-酮-17beta-醇
  参考文献：
  名称：

  Steroids. VII.¹ Contribution to the Bromination of ▵⁴-3-Ketosteroids and a New Partial Synthesis of the Natural Estrogens

  摘要：

  DOI：

  10.1021/ja01166a055

文献信息

• Synthesis of novel C17 steroidal carbamates
  作者：Vânia M.A. Moreira、Tadas S. Vasaitis、Zhiyong Guo、Vincent C.O. Njar、Jorge A.R. Salvador

  DOI：10.1016/j.steroids.2008.05.010

  日期：2008.11

  We have exploited the reaction of 1,1'-carbonylbis(2-methylimidazole) (CBMI) with several 17beta-hydroxy androstanes to synthesize a series of novel C17 steroidal carbamates. Structural elucidation features have been provided for the final compounds based on 1D and 2D NMR techniques, IR spectroscopy, and related literature. The new compounds were tested for inhibition of human cytochrome 17alpha-hydroxylase-C17

  我们利用 1,1'-羰基双 (2-甲基咪唑) (CBMI) 与几个 17beta-羟基雄甾烷的反应来合成一系列新型 C17 甾体氨基甲酸酯。已根据 1D 和 2D NMR 技术、IR 光谱和相关文献为最终化合物提供了结构解析特征。测试了新化合物对人类细胞色素 17α-羟化酶-C17,20-裂解酶 (CYP17) 和雄激素受体 (AR) 结合和功能影响的抑制作用。还评估了它们对 PC-3 细胞增殖的抑制潜力。发现化合物 11 和 23 抑制 CYP17，IC50 值分别为 17.1 和 11.5 microM。C17 处的氨基甲酸酯部分允许合成的化合物与野生型 (wt-) 和突变的 AR 紧密结合。当绑定到突变的 AR 时，发现这些化合物具有双重作用，在天然雄激素二氢睾酮 (DHT) 存在的情况下，在低浓度下刺激转录，而在测试的较高浓度下几乎完全阻断转录。化合物 8 和 12 对 PC-3 细胞增殖最有效，EC50
• Iodine, a Mild Reagent for the Aromatization of Terpenoids
  作者：Victoriano Domingo、Consuelo Prieto、Lucia Silva、Jesús M. L. Rodilla、José F. Quílez del Moral、Alejandro F. Barrero

  DOI：10.1021/acs.jnatprod.5b00914

  日期：2016.4.22

  Efficient procedures based on the use of iodine for the aromatization of a series of terpenoids possessing diene and homoallylic or allylic alcohol functionalities are described. Different examples are reported as a proof-of-concept study. Furthermore, iodine also proved to mediate the dehydrogenation of testosterone.

  描述了基于碘的使用的有效方法，该方法用于使具有二烯和均烯丙基或烯丙基醇官能度的一系列萜类化合物芳构化。报告了不同的示例作为概念验证研究。此外，碘还被证明可介导睾丸激素的脱氢。
• Chemoselective reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by various hydride reagents
  作者：Eunjeong Kim、Eunsook Ma

  DOI：10.1016/j.steroids.2006.12.008

  日期：2007.4

  The chemoselectivity of rigid cyclic alpha,omega-unsaturated carbonyl group on the reducing agents was influenced by the ring size and steric factor. Cholesterol (cholest-5-en-3 beta-ol) and dehydroepiandrosterone (DHEA) were oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione. They were reduced with NaBH4, lithium tri-sec-butylborohydride (L-Selectride), LiAlH4, 9-borabicyclo[3.3.1]nonane (9-BBN), lithium triethylborohydride (Super-hydride), and BH3.(CH3)(2)S in various conditions, respectively. Reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by NaBH4 (4 equiv.) produced 4,6-cholestadien-3 beta-ol and 4,6-androstadiene-3 beta,17 beta-diol, respectively Reduction by L-Selectride (12 equiv.) afforded 4,6-cholestadien-3 alpha-ol and 4,6-androstadiene-3 alpha,17 beta-diol, chemoselectively Reaction with Super-hydride (12 equiv.) produced 4,6-cholestadien-3-one and 3-oxo-4,6-androstadien-17 beta-ol. Reduction of 1,4,6-cholestatrien-3-one by 9-BBN (14 equiv.) produced 1,4,6-cholestatrien-3 alpha-ol, but 1,4,6-androstatriene-3,17-dione was not reacted with 9-BBN in the reaction conditions. Reaction of LiAlH4 (6 equiv.) formed 4,6-cholestadien-3 beta-ol and 3-oxo-1,4,6-androstatrien-17 beta-ol. Reduction of 1,4,6-cholestatrien-3-one by BH3.(CH3)2S (11 equiv.) gave cholestane as major compound and unlike reactivity of cholesterol, 1,4,6-androstatriene-3,17-dione by 8 equiv. of BH3.(CH3)(2)s formed 3-oxo-1,4,6-androstatrien-17 beta-ol. LiAlH4 and BH3.(CH3)(2)S showed relatively low chemoselectivity. (c) 2007 Elsevier Inc. All rights reserved.
• Pelc,B. et al., Collection of Czechoslovak Chemical Communications, 1968, vol. 33, p. 1131 - 1142
  作者：Pelc,B. et al.

  DOI：——

  日期：——
• COMPOSITIONS AND METHODS THAT TARGET OLFACTORY RECEPTORS FOR REGULATION OF BREATHING
  申请人：The Board of Trustees of the Leland Stanford Junio

  公开号：US20170100353A1

  公开（公告）日：2017-04-13

  The olfactory receptor Olfr78/OR51E2 is shown to be expressed in the carotid body and to control breathing responses regulated by acute hypoxia sensing. Activation of Olfr78/OR51E2 increases breathing, while inhibitors of the receptor can counteract this activity. A native agonist of Olfr78/OR51E2 is shown to be lactate.