5α-androstan-3β,4β,17β-triol | 59599-19-8

• 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-3β,4β,17β-triol
• 英文别名: (3S,4R,5R,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,4,17-triol
• CAS: 59599-19-8
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: UXTGTYSFGWRVQF-VKFNVQGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5α-androstan-3β,4β,17β-triol 、 乙酸酐 在 吡啶 作用下， 生成 5α-androstanetriyl-(3β.4β.17β)-triacetate
  参考文献：
  名称：

  The Z/I Imaging Digital Camera System

  摘要：

  市场对摄影测量和地理信息系统应用中使用的机载和空间图像的需求正在发生变化。传感器、平台和应用正在发生根本性的变化。最近，新的高分辨率机载传感器已经问世。除了传统的摄影测量，新的专题应用也将推动未来的图像市场。成本和时间的节省，以及对更高和可重复的辐射分辨率或光谱信息的需求，将推动模拟图像向数字图像的转变。高分辨率卫星将与机载胶片摄影和数字照相系统展开竞争。有了数字机载照相机，就有可能实现从图像采集到利用和数据分发的完整数字链。在这种情况下，相机设计的关键决定因素是应使用线性还是面积阵列传感器。鉴于摄影测量中对几何精度的高要求，Z/I Imaging 将开发重点放在了基于面积传感器的数码相机上。这一决定的一个重要方面不仅是航空摄影系统，还包括从摄影测量过程到摄影或制图成品的整个过程。从这个角度看，数码相机的开发显然不仅仅是将胶片换成硅片那么简单。数据传输速率、飞行中的数据处理和存储、图像存档、地理参照、色彩融合、校准和预处理等方面对数码相机系统的经济评估具有同样的影响。本文介绍了数字模块化机载照相机系统目前的开发活动和应用方面的情况。

  DOI：

  10.1111/0031-868x.00158
• 作为产物：
  描述：

  (3S,4R,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,4,17-triol 在 乙醇 、 溶剂黄146 、 铂 作用下， 生成 5α-androstan-3β,4β,17β-triol
  参考文献：
  名称：

  The Z/I Imaging Digital Camera System

  摘要：

  市场对摄影测量和地理信息系统应用中使用的机载和空间图像的需求正在发生变化。传感器、平台和应用正在发生根本性的变化。最近，新的高分辨率机载传感器已经问世。除了传统的摄影测量，新的专题应用也将推动未来的图像市场。成本和时间的节省，以及对更高和可重复的辐射分辨率或光谱信息的需求，将推动模拟图像向数字图像的转变。高分辨率卫星将与机载胶片摄影和数字照相系统展开竞争。有了数字机载照相机，就有可能实现从图像采集到利用和数据分发的完整数字链。在这种情况下，相机设计的关键决定因素是应使用线性还是面积阵列传感器。鉴于摄影测量中对几何精度的高要求，Z/I Imaging 将开发重点放在了基于面积传感器的数码相机上。这一决定的一个重要方面不仅是航空摄影系统，还包括从摄影测量过程到摄影或制图成品的整个过程。从这个角度看，数码相机的开发显然不仅仅是将胶片换成硅片那么简单。数据传输速率、飞行中的数据处理和存储、图像存档、地理参照、色彩融合、校准和预处理等方面对数码相机系统的经济评估具有同样的影响。本文介绍了数字模块化机载照相机系统目前的开发活动和应用方面的情况。

  DOI：

  10.1111/0031-868x.00158

文献信息

• Regioselective enzymatic acylation of vicinal diols of steroids
  作者：M. Manuel Cruz Silva、Sergio Riva、M. Luisa Sá e Melo

  DOI：10.1016/j.tet.2005.01.104

  日期：2005.3

  Monoacylated derivatives of a complete set of 2,3- and 3,4-vicinal diols of steroids were prepared by regioselective lipase-catalysed transesterification reactions. The enzymes displayed different selectivities towards the vicinal diols depending on the configuration of the hydroxyl groups.

  完整的甾族化合物的2，3-和3，4-邻位二醇的单酰化衍生物是通过区域选择性脂肪酶催化的酯交换反应制备的。取决于羟基的构型，酶对邻二醇具有不同的选择性。
• Synthesis of 4-d1-testosterone and 4-d1-androstenedione.
  作者：TOSHIO NAMBARA、SHIGEO IKEGAWA、HIDEKI ISHIDA

  DOI：10.1248/cpb.24.2486

  日期：——

  In order to clarify the stereochemistry at C-4 in enzymatic saturation of Δ4-3-ketoste-roids synthesis of 4-deuterated testosterone and androst-4-ene-3, 17-dione (XVIII, XIX) has been undertaken. The key intermediate leading to the required substrate, 4α-d1-5α-androstane-3β, 4β, 17β-triol 3, 17-bis (dimethyl-tert-butylsilyl) ether (XVI), was prepared by stereospecific reduction with lithium aluminum deuteride from 3β, 17β-dihydroxy-5α-androstan-4-one disilyl ether (XIII), which was readily obtainable from androst-4-ene-3β, 17β-diol disilyl ether (XI) by hydroboration, followed by oxidation with chromium trioxide-pyridine complex. Dehydration of XVI with phosphorus oxychloride in pyridine provided the Δ4 olefine (XVIIb) which on chromium trioxide oxidation was led to the desired compounds. Reductive dehalogenation of 4-bromotestosterone silyl ether (II) with lithium aluminum deuteride and subsequent oxidation with chromium trioxide-pyridine complex afforded 4-d1-testosterone silyl ether (VII) in which the deuterium incorporation, however, proved to be unsatisfactory.

  为了弄清Δ4-3-酮基类固醇酶饱和合成 4-氚代睾酮和雄甾-4-烯-3，17-二酮（XVIII，XIX）过程中 C-4 的立体化学结构，我们进行了一项研究。所需底物 4α-d1-5α 雄甾烷-3β，4β，17β-三醇 3，17-双（二甲基-叔丁基硅基）醚（XVI）的关键中间体是用氘化铝锂从 3β、17β-二羟基-5α-雄甾烷-4-酮二硅基醚（XIII）的立体还原，然后用三氧化铬-吡啶络合物进行氧化，制备了 3β，17β-二羟基-5α-雄甾烷-4-酮二硅基醚（XVI）。XVI 在吡啶中与氧氯化磷脱水后得到 Δ4 烯烃（XVIIb），再用三氧化铬氧化后得到所需的化合物。用氘化铝锂对 4-溴睾酮硅基醚 (II) 进行还原脱卤反应，然后用三氧化铬-吡啶络合物进行氧化，得到了 4-d1-睾酮硅基醚 (VII)。
• Role of human 3α-hydroxysteroid dehydrogenase isoforms (AKR1C1-AKR1C3) in the extrahepatic metabolism of the steroidal aromatase inactivator Formestane
  作者：Runlan Wan、Xi Kong、Youzhe Yang、Siwen Tao、Youyou Chen、Alexander Tobias Teichmann、Frank Heinrich Wieland

  DOI：10.1016/j.jsbmb.2019.105527

  日期：2020.4

  The clinical use of the steroidal aromatase inhibitor Formestane (4-hydroxandrostenedione, 4-OHA) in the treatment of advanced ER+ breast cancer has been discontinued, and therefore, interest in this remarkable drug has vanished. As a C-19 sterol, 4-OHA can undergo extensive intracellular metabolism depending on the expression of specific enzymes in the corresponding cells. We used the metabolites

  甾体芳香酶抑制剂福尔坦斯坦（4-羟氧杂戊二酮，4-OHA）在治疗晚期ER +乳腺癌中的临床应用已中止，因此，对这种显着药物的兴趣已消失。作为C-19固醇，4-OHA可以进行大量的细胞内代谢，具体取决于特定酶在相应细胞中的表达。我们使用代谢物4β-羟基雄甾酮，4β-羟基表雄酮及其17β还原衍生物作为标准，以证明存在于细胞培养基中并由分离的酶表达的催化活性。所有的醛基酮还原酶AKR1C1，AKR1C2，AKR1C3和AKR1C4均同时催化4-OHA的3-酮基和Δ4,5双键的还原。使用微尺度热泳的分子对接实验以及对带有底物4-OHA的分离酶的动力学行为的研究证明，AKR1C3对底物具有最高的亲和力，而AKR1C1是最有效的酶。两种酶（AKR1C1和AKR1C3）都在脂肪组织和肺中高表达，表现出3β-HSD活性。4-OHA产生生物活性衍生物的可能性，例如雄激素4-羟基睾丸激素或5α还原的代谢物的一
• Al-Fouti, Khaled; Hanson, James R., Journal of Chemical Research, Miniprint, 2003, # 1, p. 143 - 152
  作者：Al-Fouti, Khaled、Hanson, James R.

  DOI：——

  日期：——
• Metabolism of 4-hydroxyandrostenedione and 4-hydroxytestosterone: Mass spectrometric identification of urinary metabolites
  作者：Maxie Kohler、Maria K. Parr、Georg Opfermann、Mario Thevis、Nils Schlörer、Franz-Josef Marner、Wilhelm Schänzer

  DOI：10.1016/j.steroids.2006.11.018

  日期：2007.3

  4-Hydroxyandrost-4-ene-3,17-dione is a second generation, irreversible aromatase inhibitor and commonly used as anti breast cancer medication for postmenopausal women. 4-Hydroxytestosterone is advertised as anabolic steroid and does not have any therapeutic indication. Both substances are prohibited in sports by the World Anti-Doping Agency, and, due to a considerable increase of structurally related steroids with anabolic effects offered via the internet, the metabolism of two representative candidates was investigated.Excretion studies were conducted with oral applications of 100mg of 4-hydroxyandro-stenedione or 200mg of 4-hydroxytestosterone to healthy male volunteers. Urine samples were analyzed for metabolic products using conventional gas chromatography-mass spectrometry approaches, and the identification of urinary metabolites was based on reference substances, which were synthesized and structurally characterized by nuclear magnetic resonance spectroscopy and high resolution/high accuracy mass spectrometry.Identified phase-I as well as phase-II metabolites were identical for both substances. Regarding phase-I metabolism 4-hydroxyandrostenedione (1) and its reduction products 3 beta-hydroxy-5 alpha-androstane-4,17-dione (2) and 3 alpha-hydroxy-5 beta-androstane-4,17-dione (3) were detected. Further reductive conversion led to all possible isomers of 3 xi,4 xi-dihydroxy,-5 xi-androstan-17-one (4, 6-11) except 3 alpha,4 alpha-dihydroxy-5 beta-androstan-17-one (5).Out of the 17 beta-hydroxylated analogs 4-hydroxytestosterone (18), 3 beta,17 beta-dihydroxy-alpha-androstan-4-one (19),3 alpha,17 beta-dihydroxy-5 beta-androstan-4-one (20), 5 alpha-androstane-3 beta,4 beta,17 beta-triol (21), 5 alpha-androstane-3 alpha,4 beta,17 beta-triol (26) and 5 alpha-androstane-3 alpha,4 alpha,17 beta-triol (28) were identified in the post administration urine specimens. Furthermore 4-hydroxyandrosta-4,6-diene-3,17-dione (29) and 4-hydroxyandrosta-1,4-diene-3,17-dione (30) were determined as oxidation products. Conjugation was diverse and included glucuronidation and sulfatation. (c) 2006 Elsevier Inc. All rights reserved.