1-雄烯-3,17-二酮 | 21507-41-5

• 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-雄烯-3,17-二酮
• 英文名称: 1-androstenedione
• 英文别名: delta 4-androstene-3,17-dione；androsten-3,17-dione；1-androstendione；androstene-3,17-dione；3,17-diketoandrostene；Androst-1-ene-3,17-dione；(8R,9S,10R,13S,14S)-10,13-dimethyl-5,6,7,8,9,11,12,14,15,16-decahydro-4H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 21507-41-5
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: WJIQCDPCDVWDDE-RNQTWYFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.789
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-雄烯-3,17-二酮 、 N-甲基-N-(三甲基硅烷基)三氟乙酰胺 在 碘化铵 、 2-巯基乙醇 作用下， 反应 0.33h， 生成
  参考文献：
  名称：

  使用大气压化学电离源联用气相色谱法测定合成代谢雄激素类固醇的质谱行为。第一部分：电离

  摘要：

  合成代谢雄激素类固醇（AAS）的检测是兴奋剂控制分析中最重要的主题之一。气相色谱联用电子电离（串联）质谱分析法（GC-MS（/ MS））和液相色谱联用的质谱联用已被传统地用于此目的。但是，这两种方法仍然具有重要的局限性，因此，目前通过这些策略的组合可以检测所有AAS。替代电离技术可以最大程度地减少这些缺点，并有助于实施一种用于检测AAS的单一方法。在当前工作中，已经测试了一种商业化的气相色谱与四极杆飞行时间分析仪结合使用的新型常压化学电离（APCI）源，以评估60型AAS的电离。已对未衍生化和三甲基甲硅烷基（TMS）衍生的化合物进行了研究。使用GC–APCI–MS可以将所有测定的AAS离子化，无论其结构如何。源中水作为改性剂的存在促进了质子化分子的形成（[M + H]+），成为大多数研究化合物的光谱基峰。在这些条件下，非衍生化AAS的[M + H] +，[M + H-H 2 O] +和[M

  DOI：

  10.1002/jms.3367

文献信息

• [EN] INDOMETHACIN ANALOGS FOR THE TREATMENT OF CASTRATE-RESISTANT PROSTATE CANCER<br/>[FR] ANALOGUES DE L'INDOMÉTACINE DESTINÉS AU TRAITEMENT DU CANCER DE LA PROSTATE RÉSISTANT À LA CASTRATION
  申请人：UNIV VANDERBILT

  公开号：WO2013059245A1

  公开（公告）日：2013-04-25

  Provided are compositions for inhibiting a biological activity of an aldoketo reductase family 1, member C3 (AKR1 C3) polypeptide. In some embodiments, the compositions are indomethacin derivatives that are AKR1 C3-specific inhibitors. Also provided are methods for producing disclosed indomethacin derivatives that substantially lack cyclooxygenase inhibitory activity but that have AKR1C3 inhibitory activity, methods for inhibiting AKR1C3 polypeptide biological activities, and methods for treating prostate tumors in subjects.

  提供了用于抑制醛酮还原酶家族1成员C3（AKR1 C3）多肽的生物活性的组合物。在某些实施例中，这些组合物是吲哚美酸衍生物，是AKR1 C3特异性抑制剂。还提供了生产所述吲哚美酸衍生物的方法，这些衍生物基本缺乏环氧合酶抑制活性，但具有AKR1C3抑制活性，以及抑制AKR1C3多肽生物活性的方法，以及治疗受试者前列腺肿瘤的方法。
• Selective thioketalization process, process for preparing thioenol ethers from thioketals, and process for the preparation of thioketals
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0524813A1

  公开（公告）日：1993-01-27

  A selective thioketalization process for the preparation of a thioketal from a dione where one, but not the other, keto group of the dione is α,β-unsaturated, and where selective thioketalization occurs at the keto group of the dione which is not α,β-unsaturated, comprising the step of contacting the dione with a thiol, in the presence of a protic acid catalyst which is a complex of a Lewis acid and a protic source, wherein the temperature of the reaction medium is maintained below about 25°C during the reaction. Preferably, further, (i) the acid catalyst is employed in excess and/or (ii) the thiol is employed in excess. The inventive process may be employed, for example, in the preparation of a 3-keto,17-thioketalandrostene from the corresponding 3,17-diketoandrostene. A process for the preparation of thioenolethers from thioketals, especially 3-keto,17-thioenoletherandrostenes from 3-keto,17-thioketalandrostenes, wherein the thioketal is contacted with a protic acid catalyst. A process for the preparation of thioketals, especially mixed thioketals such as mixed 3-keto,17-thioketalandrostenes, from thioenolethers, comprising the step of contacting a thioenolether with a thiol in the presence of a protic acid catalyst.

  一种选择性硫醚化过程，用于从二酮制备硫醚，其中二酮的一个但不是另一个酮基是α，β-不饱和的，选择性硫醚化发生在不是α，β-不饱和的酮基上，包括将二酮与硫醇接触，在存在Lewis酸和质子源的复合物的质子酸催化剂的情况下，反应介质的温度在反应过程中保持在大约25°C以下。最好，进一步，(i) 过量使用酸催化剂和/或 (ii) 过量使用硫醇。该创新过程可以用于从相应的3,17-二酮雄烯制备3-酮，17-硫醚雄烯。一种从硫醚制备硫烯醚的过程，特别是从3-酮，17-硫醚雄烯制备3-酮，17-硫烯醚雄烯的过程，其中硫醚与质子酸催化剂接触。一种从硫烯醚制备硫醚的过程，特别是从硫烯醚制备混合硫醚，例如混合的3-酮，17-硫醚雄烯，包括将硫烯醚与硫醇在质子酸催化剂的存在下接触的步骤。
• [EN] 2-BETA-NAPHTHYL-ACETIC ACID ANALOGS AS AKR1C3 INHIBITORS AND METHODS OF USING SAME<br/>[FR] ANALOGUES DE L'ACIDE 2-BÊTA-NAPHTHYL-ACÉTIQUE COMME INHIBITEURS D'AKR1C3 ET PROCÉDÉS LES UTILISANT
  申请人：UNIV PENNSYLVANIA

  公开号：WO2017070448A1

  公开（公告）日：2017-04-27

  The invention includes 2-β-naphthyl-acetic acid derivatives, which are selective AKR1C3 inhibitors. In certain embodiments, the compounds of the invention are R-naproxen analogs. The invention further includes methods of treating cancer, such as prostate cancer and/or castration-resistant prostate cancer, using at least one compound of the invention.

  本发明涉及2-β-萘乙酸衍生物，这些衍生物是选择性的AKR1C3抑制剂。在某些实施例中，本发明的化合物是R-萘普生的类似物。本发明还涉及使用本发明中至少一种化合物治疗癌症，例如前列腺癌和/或去势抵抗性前列腺癌的方法。
• METHODS FOR PREPARING SYNTHETIC BILE ACIDS AND COMPOSITIONS COMPRISING THE SAME
  申请人：Moriarty Robert M.

  公开号：US20130261317A1

  公开（公告）日：2013-10-03

  This invention relates generally to methods for preparing certain bile acids from non-mammalian sourced starting materials as well as to synthetic bile acids and compositions comprising such acids wherein the acids are characterized by a different C 14 population than naturally occurring bile acids as well as being free from any mammalian pathogens. This invention is also directed to the synthesis of intermediates useful in the synthesis of such bile acids. Accordingly, the C ring of the steroidal scaffold is oxidized to provide a synthetic route and intermediates to DCA. This invention also provides synthetic methods for preparing deoxycholic acid or a salt thereof starting from aromatic steroids such as estrogen, equilenin, and derivatives thereof. This invention is also directed to intermediates such as 12-oxo or delta-9,11-ene steroids as well as novel processes for their preparation. In preferred embodiments, bile acids are provided herein which have substituents on the B-ring and/or D-ring side chain and optionally on the hydroxy group of the A-ring.

  本发明涉及从非哺乳动物来源的起始材料制备某些胆汁酸的方法，以及合成胆汁酸和包含这些酸的组合物，其中这些酸的特征是具有与自然存在的胆汁酸不同的C14种群，并且不含任何哺乳动物病原体。本发明还涉及合成在合成这种胆汁酸中有用的中间体。因此，甾体骨架的C环被氧化以提供合成路线和到DCA的中间体。本发明还提供了用芳香族类固醇（如雌激素、雌烯酮及其衍生物）起始制备脱氧胆酸或其盐的合成方法。本发明还涉及12-氧代或δ-9,11-烯类固醇等中间体以及其制备的新型过程。在首选实施例中，本发明提供了具有B环和/或D环侧链以及可选地具有A环羟基上取代基的胆汁酸。
• 6, 7-Oxygenated steroids and uses related thereto
  申请人：Inflazyme Pharmaceuticals Ltd.

  公开号：US20040157814A1

  公开（公告）日：2004-08-12

  Steroid compounds having various oxygen substitution on the steroid nucleus are disclosed. A specific functionality present on many of the steroid compounds is oxygen substitution at both of positions 6 and 7. Thus, certain steroids have oxygen substitution at C6 and C7, and some have specific stereochemistries such as 6&agr; and 7&bgr; oxygen substitution, and an alpha hydrogen at the 5 position in addition to having 6&agr; and 7&bgr; oxygen substitution. Steroids having 3,4-epoxy functionality are also disclosed. In addition, steroids having C17 pyran and &dgr;-lactone functionality, with oxygen substitution at C6 and C7, or at C15, of the steroid nucleus, are disclosed.

  揭示了在类固醇核上具有各种氧替代的类固醇化合物。许多类固醇化合物上具有的一种特定的功能是在6和7的位置都有氧替代。因此，某些类固醇具有C6和C7的氧替代，有些具有特定的立体化学，例如6&agr;和7&bgr;的氧替代，并且在5位置还具有一个α-氢原子，除了具有6&agr;和7&bgr;的氧替代。还披露了具有3,4-环氧功能的类固醇。此外，还揭示了具有C17吡喃和&dgr;-内酯功能，在类固醇核的C6和C7或C15处具有氧替代的类固醇。