3a-羟基雄甾-4-烯-17-酮 | 571-44-8

• 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
• 中文名称: 3a-羟基雄甾-4-烯-17-酮
• 英文名称: 4-Androstene-3alpha-ol-17-one
• 英文别名: 3α-hydroxy-4-androsten-17-one；3α-hydroxyandrost-4-en-17-one；4-androsten-3α-ol-17-one；3α-hydroxy-androst-4-en-17-one；3α-Hydroxy-androst-4-en-17-on；3alpha-Hydroxyandrost-4-en-17-one；(3R,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
• CAS: 571-44-8；86420-28-2；2791-99-3
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: VMYTXBKVYDESSJ-HKQXQEGQSA-N

物化性质

• 熔点：
  144-146 °C
• 沸点：
  428.5±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  3a-羟基雄甾-4-烯-17-酮 在 rabbit 3-hydroxyhexobarbital dehydrogenase (AKR₁C₂₉) 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 aq. phosphate buffer 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 雄烯二酮
  参考文献：
  名称：

  兔3-羟基己糖巴比妥脱氢酶是一种NADPH优先的还原酶，对酮类固醇，前列腺素D（2）以及其他内源性和异源性羰基化合物具有广泛的底物特异性。

  摘要：

  3-羟基己异巴比妥脱氢酶（3HBD）催化将NAD（P）（+）链接的3-羟基己异巴比妥氧化为3-羟基己异巴比妥。该酶被认为是异生物醇和某些羟基类固醇的脱氢酶，但其生理功能仍然未知。我们已经纯化了兔3HBD，分离了其cDNA，并检查了其对辅酶和底物的特异性，反应方向性和组织分布。3HBD是醛酮还原酶（AKR）超家族的成员（AKR1C29），并且在7.4的生理pH值下，NADP（H）优于NAD（H）。在与NADPH相关的还原反应中，3HBD对多种醌，酮和醛（包括3-，17-和20-酮类固醇和前列腺素D（2））显示出广泛的底物特异性，它们被转化为3alpha-，17beta-和20alpha -羟基类固醇和9alpha，11beta-前列腺素F（2），分别。特别是，α-二酮（如isatin和diacetyl）和脂质过氧化衍生的醛（如4-oxo-和4-hydroxy-2-nonenals）是显示低K（m）值（0

  DOI：

  10.1016/j.bcp.2013.08.024
• 作为产物：
  描述：

  雄烯二酮 在 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 (3beta)-3-羟基雄甾-4-烯-17-酮 、 3a-羟基雄甾-4-烯-17-酮
  参考文献：
  名称：

  烯丙基性腺类固醇、3α-hydroxy-4-pregnen-20-one 和 3α-hydroxy-4-androsten-17-one 以及 3α-hydroxy-5α-pregnen-20-one 的合成

  摘要：

  摘要 一种方便合成最近分离的烯丙基性腺类固醇 3 α -羟基-4-孕烯-20-酮 (3 α -二氢孕酮; 3 α -DHP) 和 3 α -羟基-4-雄甾烯-17-的方法一种 (3 α -HA)，是使用 4-pregnene-3,20-dione（孕酮）和 4-androstene-3,17-dione 作为底物和三甲基硼氢化钾（KS-Selectride）作为还原剂开发的。类似的反应也用于将 5 α -pregnan-3,20-dione 还原为 3 α -hydroxy-5 α -pregnan-20-one (3 α -HP)。3α-DHP、3α-HA和3α-HP的产率分别为约15%、50%和>90%。在这些反应中形成的产物的结构，包括 3 β -异构体和 17 α -差向异构体，通过核磁共振和质谱方法确定。

  DOI：

  10.1016/0039-128x(85)90064-9

文献信息

• Cyclopentanperhydrophenanthren-17.beta.-(hydroxy or
  申请人：Sigma-Tau Industrie Farmceutiche Riunite S.p.A.

  公开号：US05521167A1

  公开（公告）日：1996-05-28

  The present invention relates to new cyclopentanperhydrophenanthren-17-(hydroxy or alkoxy)-17-(aryl or heterocyclyl)-3.beta.-derivatives, active on the cardiovascular system, to a process for their preparation and to pharmaceutical compositions containing them. The invention relates to compounds of general formula (I) ##STR1## wherein X is O or S and R, R.sup.1 and R.sup.2 is selected from various groups.

  本发明涉及新的环戊烷基氢化苯并环十七醇基或烷氧基)-十七芳基或杂环烷基)-3-β-衍生物，对心血管系统具有活性，以及其制备方法和含有它们的药物组合物。该发明涉及一般式（I）的化合物 ##STR1## 其中X为O或S，R、R.sup.1和R.sup.2选择自不同的基团。
• Substrate Specificity of a Mouse Aldo-Keto Reductase (AKR1C12)
  作者：Satoshi Endo、Kengo Matsumoto、Toshiyuki Matsunaga、Shuhei Ishikura、Kazuo Tajima、Ossama El-Kabbani、Akira Hara

  DOI：10.1248/bpb.29.2488

  日期：——

  AKR1C12, a mouse member of the aldo-keto reductase (AKR) superfamily, is highly expressed in the stomach and is identical to a protein encoded in an interleukin-3-regulated gene in mouse myeloid cells, but its function remains unknown. In this study, the recombinant AKR1C12 was purified to homogeneity and the specificity for coenzymes and substrates was examined at a physiological pH of 7.4. The enzyme reduced various α-dicarbonyl compounds, several ketosteroids, aldehydes and some ketones using NADH as the preferred coenzyme. In the reverse reaction, the enzyme showed coenzyme preference for NAD+, and oxidized 3α-, 17β- and 20α-hydroxysteroids, and non-steroidal aliphatic and alicyclic alcohols, of which many hydroxysteroids and geranylgeraniol were good substrates, exhibiting low Km and high kcat/Km values. The results, together with the intracellular high ratio of NAD+/NADH, suggest that AKR1C12 functions as a dehydrogenase for the endogenous hydroxysteroids and geranylgeraniol in mouse stomach and myeloid cells.

  AKR1C12是醛酮还原酶（AKR）超家族的小鼠成员，在胃中高表达，与小鼠髓系细胞中白细胞介素-3调控基因编码的蛋白相同，但其功能仍不清楚。本研究纯化了重组 AKR1C12，并在生理 pH 值为 7.4 的条件下检测了其对辅酶和底物的特异性。该酶以 NADH 为首选辅酶，还原了各种 α-二羰基化合物、几种类固醇、醛类和一些酮类化合物。在反向反应中，该酶表现出对 NAD+ 的辅酶偏好，可氧化 3α-、17β- 和 20α-羟基类固醇、非类固醇脂肪醇和脂环醇，其中许多羟基类固醇和香叶醇是良好的底物，表现出较低的 Km 值和较高的 kcat/Km 值。这些结果以及细胞内 NAD+/NADH 的高比率表明，AKR1C12 在小鼠胃和髓系细胞中发挥着内源性羟基类固醇和香叶醇脱氢酶的功能。
• New cyclopentanperhydrophenanthren-17beta-(hydroxy or alkoxy)-17alpha-(aryl or heterocyclyl)-3beta-derivatives active on the cardiovascular system, processes for their preparation and pharmaceutical compositions containing same
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0590489A2

  公开（公告）日：1994-04-06

  Cyclopentanperhydrophenanthren-17-(hydroxy or alkoxy)-17-(aryl or heterocyclyl)-3β-derivatives of general formula (I): wherein: the symbol means that the hydrogen in position 5 can have an a or configuration; the symbol represents either a single or a double bond; and X, R, R1 and R2 have the meanings given in the description; a process for producing same and their use for the preparation of a medicament for the treatment of cardiavascular disorders such as heart failure and hypertension is disclosed.

  通式(I)的环戊四氢菲-17-(羟基或烷氧基)-17-(芳基或杂环基)-3β-衍生物： 其中 符号表示位置 5 的氢可以是 a 或构型； 符号表示单键或双键； X、R、R1 和 R2 具有说明中给出的含义； 本发明公开了制备上述物质的工艺及其用于制备治疗心血管疾病（如心力衰竭和高血压）的药物。
• New Structure–Activity Relationships of A- and D-Ring Modified Steroidal Aromatase Inhibitors: Design, Synthesis, and Biochemical Evaluation
  作者：Carla Varela、Elisiário J. Tavares da Silva、Cristina Amaral、Georgina Correia da Silva、Teresa Baptista、Stefano Alcaro、Giosuè Costa、Rui A. Carvalho、Natércia A. A. Teixeira、Fernanda M. F. Roleira

  DOI：10.1021/jm300262w

  日期：2012.4.26

  A- and D-ring androstenedione derivatives were synthesized and tested for their abilities to inhibit aromatase. In one series, C-3 hydroxyl derivatives were studied leading to a very active compound, when the C-3 hydroxyl group assumes 3 beta stereochemistry (1, IC50 = 0.18 mu M). In a second series, the influence of double bonds or epoxide functions in different positions along the A-ring was studied. Among epoxides, the 3,4-epoxide 15 showed the best activity (IC50 = 0.145 mu M) revealing the possibility of the 3,4-oxiran oxygen resembling the C-3 carbonyl group of androstenedione. Among olefins, the 4,5-olefin 12 (IC50 = 0.135 mu M) revealed the best activity, pointing out the importance of planarity in the A,B-ring junction near C-5. C-4 acetoxy and acetylsalicyloxy derivatives were also studied showing that bulky substituents in C-4 diminish the activity. In addition, IFD simulations helped to explain the recognition of the C-3 hydroxyl derivatives (1 and 2) as well as 15 within the enzyme.
• Use of DHEA derivatives for enhancing physical performance
  申请人：Marchewitz Eric

  公开号：US20060241093A1

  公开（公告）日：2006-10-26

  A method is disclosed for administering a DHEA derivative or a physiologically acceptable salt, ester or ether thereof for one of decreasing body weight, reducing adipose tissue, increasing endurance, as an anti-aging compound and generating production of red blood cells.