5α-androstan-3-one-17-ethyleneketal | 15807-55-3

• 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: 5α-androstan-3-one-17-ethyleneketal
• 英文别名: spiro[[5α]-androstane-17,2'-[1,3]-dioxolan]-3-one；17-(Ethylenedioxy)-5α-androstan-3-one；3-oxo-5α-androstane-17-dioxolane；(5S,8R,9S,10S,13S,14S)-10,13-dimethyltetradecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3(2H)-one；(5α)-androstane-3,17-dione 17-(1,2-ethanediyl acetal)；androstane-3,17-dion-17-ethyleneketal；(5α)-androstane-3,17-dione；(5'S,8'R,9'S,10'S,13'S,14'S)-10',13'-dimethylspiro[1,3-dioxolane-2,17'-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene]-3'-one
• CAS: 15807-55-3
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: SLODIKZFXFILEX-PYNNRZRQSA-N

物化性质

• 熔点：
  182-185 °C
• 沸点：
  444.8±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5α-androstan-3-one-17-ethyleneketal 在 盐酸 、 正丁基锂 、 高氯酸 、 magnesium 、 1,2-二溴乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 79.5h， 生成 2-anthracen-9-yl-5-[(5S,8R,9S,10S,13S,14S,17E)-10,13-dimethyl-17-[(5-thiophen-2-ylthiophen-2-yl)methylidene]-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl]thiophene
  参考文献：
  名称：

  Steroid-Bridged Anthryloligothienylporphyrins:  Synthesis and Study on the Intramolecular Energy Transfer

  摘要：

  The novel steroid-bridged energy transfer system 2 was prepared starting from epi-androsterone, The linkage of both the anthrylthienyl and the bithienyl group in the 3- and 17-position of the steroid was achieved by Grignard reaction of the respective carbonyl function of the steroid component. The synthesis was accomplished by linkage of the porphyrin group according to Lindsey's method. This synthetic strategy also enables the approach to molecular subunits required as reference compounds. The photophysical properties were studied using time-resolved fluorescence and fluorescence excitation spectroscopy. Reference donor molecule 6 exhibits-in analogy to other anthryloligothiophenes studied-a dual fluorescence: a blue anthracene-like fluorescence and a dynamically coupled delayed red fluorescence resulting from the relaxed excited state. On the basis of these results, supermolecule 2 was investigated. Besides the typical porphyrin emission, a high energetic fluorescence (blue fluorescence) was detected in 2 which results unambiguously, as stated from spectra of 6, from the donor part of 2. The lifetime of this fluorescence is shortened compared with that of 6. Supermolecule 2 is the first in the series of our energy transfer systems exhibiting donor fluorescence despite a very efficient intramolecular energy transfer (at least 99%).

  DOI：

  10.1021/jo980251e
• 作为产物：
  描述：

  去氢表雄酮 在 D(+)-10-樟脑磺酸 、 氨 、 aluminum isopropoxide 、 lithium 作用下， 以 四氢呋喃 、 环己酮 、 甲苯 、 苯 为溶剂， 反应 5.5h， 生成 5α-androstan-3-one-17-ethyleneketal
  参考文献：
  名称：

  Design and Synthesis of Non-peptide RGD Mimics for Evaluation of Their Utility as Anti-platelet Agents

  摘要：

  合成了Arg-Gly-Asp（RGD）模拟物并评估了它们的抗血小板活性。开发了一种简便的方法，从脱氢表雄酮、Wieland-Miescher酮和Hajos-Parrish酮合成目标化合物，这些酮适用于易于获得的平台。在合成的化合物中，具有3-(4-哌啶基)丙氧基结构的全氢萘框架3e表现出最高的抗聚集活性。3e的IC50值分别为0.91 mM（ADP诱导）和0.54 mM（胶原蛋白诱导）。

  DOI：

  10.1248/cpb.c16-00594

文献信息

• Design, chemical synthesis and biological evaluation of 3-spiromorpholinone/3-spirocarbamate androsterone derivatives as inhibitors of 17β-hydroxysteroid dehydrogenase type 3
  作者：Guy Bertrand Djigoué、Lucie Carolle Kenmogne、Jenny Roy、René Maltais、Donald Poirier

  DOI：10.1016/j.bmc.2015.07.049

  日期：2015.9

  17β-Hydroxysteroid dehydrogenase type 3 (17β-HSD3) is a key enzyme involved in the biosynthesis of testosterone and dihydrotestosterone. These hormones are known to stimulate androgen-dependent prostate cancer. In order to generate effective inhibitors of androgen biosynthesis without androgenic effect, we synthesized a new family of 3-spiromorpholinone and 3-spirocarbamate androsterone derivatives

  17β-羟基类固醇脱氢酶3（17β-HSD3）是参与睾丸激素和二氢睾丸激素生物合成的关键酶。已知这些激素可刺激雄激素依赖性前列腺癌。为了产生没有雄激素作用的雄激素生物合成的有效抑制剂，我们合成了带有多个疏水基团的新的3-spiromorpholinone和3-spirocarbamate雄甾酮衍生物家族。我们还测试了它们在含有17β-HSD3的大鼠睾丸的微粒体中的抑制活性，以及​​它们对雄激素敏感性LAPC-4细胞的雄激素作用。从我们的第一个结构-活性关系（SAR）研究中，我们注意到化合物7e与我们的参考化合物RM-532-105（0.1μM时76％）相比，抑制17β-HSD3（0.1μM时77％），但表现出残留的雄激素作用。接下来合成7e类似化合物的文库，以生成具有降低的雄激素活性的化合物。在这项新的SAR研究中，磺酰胺化合物7e21和羧酰胺化合物7e22抑制了17β-HSD3（IC 50分别 为28和88
• Synthesis and Optimization of a New Family of Type 3 17β-Hydroxysteroid Dehydrogenase Inhibitors by Parallel Liquid-Phase Chemistry
  作者：René Maltais、Van Luu-The、Donald Poirier

  DOI：10.1021/jm010286y

  日期：2002.1.1

  (D) of 3-carbamate-ADT derivatives (25 members) using the efficient parallel liquid-phase method III, which allowed the synthesis of more rigid molecules with two levels of molecular diversity (R(1)/R(2) and R(3)) in the local area occupied by the adamantane group of C-7-3. Interestingly, one of the most potent inhibitors of library D, the 3R-spiro-[3'-[3' '-N-morpholino-2' '-(3' "-cyclopentyl-prop

  3型17β-羟基类固醇脱氢酶（17 beta-HSD）将4-雄烯3,17-二酮（Delta（4）-二酮）转化为雄激素睾丸激素。为了生产这种关键的类固醇生成酶的有效抑制剂，我们以较高的收率和平均高效液相色谱（HPLC）纯度为92-94％进行了3beta-取代的雄甾酮（ADT）文库（AD）的并行液相合成。使用并行液相法合成了3个β-氨基甲基ADT衍生物（168个成员）的第一文库（A），其中包括酰胺上的两个分子多样性水平（R（1）和R（2））（方法I）比传统的化学方法花费的时间更少。库A的筛选显示，R（1）（5-8个碳）处的疏水链相对较小，R（2）（1-4个碳）处的疏水取代基较小，提供了最有效的抑制剂。根据这些抑制结果，使用基于清除剂树脂和液相平行化学的改进方法，在很短的时间内生成了3个β-氨基甲基-ADT衍生物（56个成员）的第二个文库（B）。库B比库A产生了更强的抑制剂，并提供了有用的结构-
• [EN] NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF<br/>[FR] STÉROÏDES NEUROACTIFS, COMPOSITIONS ET LEURS UTILISATIONS
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2013036835A1

  公开（公告）日：2013-03-14

  Compounds are provided according to Formula (I) and pharmaceutically acceptable salts thereof, wherein Z is a group of the formula (i), (ii), (iii), (iv), or (v), and wherein L1, L2, L3, X1, X2, Y, Rz4, Rz5, Rz6, n, R1, R2, R3a, R3b, R4a, R4b, R6a, R6b, R7a, R7b, R11a, R11b, R14, R17, R19, R20, R23a, R23b, and R24 are as defined herein, and pharmaceutical compositions thereof. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of CNS-related conditions in mammals.

  根据公式（I）提供化合物及其药学上可接受的盐，其中Z是公式（i）、（ii）、（iii）、（iv）或（v）的基团，L1、L2、L3、X1、X2、Y、Rz4、Rz5、Rz6、n、R1、R2、R3a、R3b、R4a、R4b、R6a、R6b、R7a、R7b、R11a、R11b、R14、R17、R19、R20、R23a、R23b和R24如本文所定义，并且其药物组合物。本发明的化合物被认为对哺乳动物的多种与中枢神经系统相关的疾病的预防和治疗有用。
• NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
  申请人：SAGE THERAPEUTICS, INC.

  公开号：US20160022701A1

  公开（公告）日：2016-01-28

  Provided are methods of evaluating or treating a patient, e.g., a patient having a disorder described herein, comprising: a) optionally, acquiring a patient sample; b) acquiring an evaluation of and/or evaluating the sample for an alteration in the level S24(S)-hydroxycholesterol compared to a reference standard.

  提供了评估或治疗患者的方法，例如，患有本文所述疾病的患者，包括：a) 可选地，获取患者样本；b) 获取对样本的评估和/或评估其S24(S)-羟基胆固醇水平与参考标准相比是否发生改变。
• NOVEL CYP17 INHIBITORS
  申请人：Chu Daniel

  公开号：US20110178065A1

  公开（公告）日：2011-07-21

  Provided herein are inhibitors of CYP17 enzyme. Also described herein are pharmaceutical compositions that include at least one compound described herein and the use of a compound or pharmaceutical composition described herein to treat androgen-dependent diseases, disorders and conditions.

  本文提供了CYP17酶的抑制剂。本文还描述了包括本文所述至少一种化合物的药物组合物，以及使用本文所述的化合物或药物组合物来治疗雄激素依赖性疾病、疾病和症状。