androst-4-ene-1α,17β-diol-3-one | 70702-34-0

• 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: androst-4-ene-1α,17β-diol-3-one
• 英文别名: 1α-hydroxytestosterone；1α,17β-dihydroxy-androst-4-en-3-one；1α,17β-Dihydroxy-androst-4-en-3-on；1α,17β-Dihydroxy-androst-4-en-3-on, 1α-Hydroxy-testosteron；1α-Hydroxy-testosteron；1alpha-Hydroxytestosterone；(1S,8S,9S,10R,13S,14S,17S)-1,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 70702-34-0
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: LUWKGSHFDJJDAJ-LOVVWNRFSA-N

物化性质

• 熔点：
  248-253 °C
• 沸点：
  478.0±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  雄烯二酮 在 sodium tetrahydroborate 作用下， 生成 androst-4-ene-1α,17β-diol-3-one
  参考文献：
  名称：

  Microbiological Transformations. V. 1α- and 2β-Hydroxylations of C₁₉-Steroids

  摘要：

  DOI：

  10.1021/ja01500a054

文献信息

• Synthesis of hydroxylated steroid hormones via conjugate addition of a silyl-cuprate reagent
  作者：Diana Garside、David N. Kirk、Norman M. Waldron

  DOI：10.1016/0039-128x(94)90102-3

  日期：1994.12

  several hydroxylated steroids via conjugate addition of Fleming's silyl-cuprate reagent, (PhMe2Si)2CuLi, a masked hydroxyl group, to the appropriate enone was studied. By this means 7 alpha-hydroxytestosterone (7) was obtained in good yield from 17 beta-hydroxyandrosta-4,6-dien-3-one (1a), though similar reactions on 17 beta-hydroxyandrosta-1,4-dien-3-one (8) gave a low yield of 1 alpha-hydroxytestosterone

  研究了通过将Fleming的甲硅烷基-杯酸酯试剂（PhMe2Si）2CuLi，一种被掩蔽的羟基缀合到适当的烯酮中来合成几种羟基化的类固醇。通过这种方法，从17个β-羟基雄甾烯-4,6-dien-3-one（1a）以良好的收率获得了7个α-羟基睾丸激素（7），尽管对17个β-羟基雄甾烯-1,4-dien-3的反应相似-一（8）产生低产率的1α-羟基睾丸酮（13）的主要原因是苯基甲硅烷基中间体向卤代硅烷的转化率低。以类似的方式从3 beta-hydroxy-5 alpha-pregn-16-en-20-one和5 alpha-cholestane-1获得3 beta，16 alpha-Dihydroxy-5 alpha-pregnan-20-one（18b）。通过共轭加成甲硅烷基，还原羰基官能团，由1-en-3-one（14）生成alpha，3 alpha-diol（17），
• Substrate Hunting for the Myxobacterial CYP260A1 Revealed New 1α-Hydroxylated Products from C-19 Steroids
  作者：Yogan Khatri、Michael Ringle.、Michael Lisurek、Jens Peter von Kries、Josef Zapp、Rita Bernhardt

  DOI：10.1002/cbic.201500420

  日期：2016.1

  The first 1α: CYP260A1 performed predominant 1α‐hydroxylation of testosterone, androstenedione, and 11‐oxoandrostenedione; however, testosterone acetate was hydroxylated at both the 1α‐ and the 9α‐positions. This hydroxylation offers scope for further chemical modification at the steroidal C‐1 position, which is of significant pharmaceutical interest.

  第一个1α：CYP260A1主要执行1α-羟化睾丸激素，雄烯二酮和11-氧雄烯二酮; 然而，醋酸睾丸激素在1α和9α位置均被羟基化。这种羟基化作用为在甾体C-1位进一步化学修饰提供了空间，这在制药上具有重要意义。
• Synthesis of 1-α-hydroxytestosterone
  作者：John Mann、Barbara Pietrzak

  DOI：10.1016/0040-4020(89)80153-x

  日期：1989.1
• 3-oxygenated 4-androstene-1, 17-diols and derivatives
  申请人：SEARLE &

  公开号：US02833794A1

  公开（公告）日：1958-05-06
• Genome Mining in Sorangium cellulosum So ce56
  作者：Kerstin Maria Ewen、Frank Hannemann、Yogan Khatri、Olena Perlova、Reinhard Kappl、Daniel Krug、Jürgen Hüttermann、Rolf Müller、Rita Bernhardt

  DOI：10.1074/jbc.m109.021717

  日期：2009.10

  Myxobacteria, especially members of the genus Sorangium, are known for their biotechnological potential as producers of pharmaceutically valuable secondary metabolites. The biosynthesis of several of those myxobacterial compounds includes cytochrome P450 activity. Although class I cytochrome P450 enzymes occur wide-spread in bacteria and rely on ferredoxins and ferredoxin reductases as essential electron mediators, the study of these proteins is often neglected. Therefore, we decided to search in the Sorangium cellulosum So ce56 genome for putative interaction partners of cytochromes P450. In this work we report the investigation of eight myxobacterial ferredoxins and two ferredoxin reductases with respect to their activity in cytochrome P450 systems. Intriguingly, we found not only one, but two ferredoxins whose ability to sustain an endogenous So ce56 cytochrome P450 was demonstrated by CYP260A1-dependent conversion of nootkatone. Moreover, we could demonstrate that the two ferredoxins were able to receive electrons from both ferredoxin reductases. These findings indicate that S. cellulosum can alternate between different electron transport pathways to sustain cytochrome P450 activity.