21-去氢皮质醇 | 14760-49-7

• 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: 21-去氢皮质醇
• 中文别名: 氢化可松EP杂质G
• 英文名称: 11β,17α-dihydroxy-3,20-dioxopregn-4-en-21-al
• 英文别名: 21-dehydrocortisol；2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoacetaldehyde
• CAS: 14760-49-7
• 化学式: C₂₁H₂₈O₅
• 分子量: 360.45
• InChiKey: JIELFMXLFHFDRT-VWUMJDOOSA-N

物化性质

• 熔点：
  154-156°C
• 沸点：
  536.1±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  21-去氢皮质醇 在 sodium hydroxide 、 silver(l) oxide 作用下， 反应 1.0h， 以40%的产率得到11β,17-dihydroxy-3,20-dioxopregn-4-en-21-oic acid
  参考文献：
  名称：

  An improved method for the chemical synthesis of steroidal 20-oxo-21-oic acids

  摘要：

  A procedure is described for the chemical synthesis of steroidal-20-oxo-21-oic acids and -17 alpha(-hydroxy-20-oxo-21-oic acids. Corticosteroid derivatives containing the 20-oxo-21-aldehyde side chain are oxidized with freshly generated silver oxide in dilute aqueous sodium hydroxide.

  DOI：

  10.1016/0039-128x(83)90118-6
• 作为产物：
  描述：

  氢化可的松 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 吡啶 、 氧气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 21-去氢皮质醇
  参考文献：
  名称：

  选择性Cu(I)催化氧化α-羟基酮合成α-酮醛

  摘要：

  通过以氧气为氧化剂，Cu( I )催化α-羟基酮选择性氧化，建立了一种合成α-酮醛的有效方法。制备了多种 α-酮醛，分离产率高达 87%。该反应的潜在利用通过克级反应和合成应用进行了评估。

  DOI：

  10.1039/d2cc00773h

文献信息

• General method for determination of configuration of steroid-17-yl methyl glycolates at C-20.
  作者：Toshio SUZUKI、Hitoshi TADA、Yasuyuki MATSUDA、Xiao-hong YANG、Katsuo UNNO

  DOI：10.1248/cpb.41.1481

  日期：——

  Kinetic examination for methoxycarbonylations of the isomeric steroid-17-yl methyl glycolates at C-20 and plots of the amount of each isomer produced by a reaction of their corresponding steroids with cupric acetate in absolute methanol provide a general and facile method for determination of the configuration of the steroid-17-yl methyl glycolates at C-20.

  对 C-20 位的甾体-17-基甲基羟基化合物异构体的甲氧基羰基化进行动力学检查，并绘制出相应的甾体与醋酸铜在绝对甲醇中反应生成的每种异构体的量，为确定 C-20 位的甾体-17-基甲基羟基化合物的构型提供了一种通用而简便的方法。
• Expanded substrate screenings of human and Drosophila type 10 17β-hydroxysteroid dehydrogenases (HSDs) reveal multiple specificities in bile acid and steroid hormone metabolism: characterization of multifunctional 3α/7α/7β/17β/20β/21-HSD
  作者：Naeem SHAFQAT、Hanns-Ulrich MARSCHALL、Charlotta FILLING、Erik NORDLING、Xiao-Qiu WU、Lars BJÖRK、Johan THYBERG、Eva MÅRTENSSON、Samina SALIM、Hans JÖRNVALL、Udo OPPERMANN

  DOI：10.1042/bj20030877

  日期：2003.11.15

  17β-Hydroxysteroid dehydrogenases (17β-HSDs) catalyse the conversion of 17β-OH (-hydroxy)/17-oxo groups of steroids, and are essential in mammalian hormone physiology. At present, eleven 17β-HSD isoforms have been defined in mammals, with different tissue-expression and substrate-conversion patterns. We analysed 17β-HSD type 10 (17β-HSD10) from humans and Drosophila, the latter known to be essential in development. In addition to the known hydroxyacyl-CoA dehydrogenase, and 3α-OH and 17β-OH activities with sex steroids, we here demonstrate novel activities of 17β-HSD10. Both species variants oxidize the 20β-OH and 21-OH groups in C21 steroids, and act as 7β-OH dehydrogenases of ursodeoxycholic or isoursodeoxycholic acid (also known as 7β-hydroxylithocholic acid or 7β-hydroxyisolithocholic acid respectively). Additionally, the human orthologue oxidizes the 7α-OH of chenodeoxycholic acid (5β-cholanic acid, 3α,7α-diol) and cholic acid (5β-cholanic acid). These novel substrate specificities are explained by homology models based on the orthologous rat crystal structure, showing a wide hydrophobic cleft, capable of accommodating steroids in different orientations. These properties suggest that the human enzyme is involved in glucocorticoid and gestagen catabolism, and participates in bile acid isomerization. Confocal microscopy and electron microscopy studies reveal that the human form is localized to mitochondria, whereas Drosophila 17β-HSD10 shows a cytosolic localization pattern, possibly due to an N-terminal sequence difference that in human 17β-HSD10 constitutes a mitochondrial targeting signal, extending into the Rossmann-fold motif.

  17β-羟类固醇脱氢酶（17β-HSDs）催化类固醇中 17β-OH （-羟基）/17-氧代基团的转化，是哺乳动物激素生理过程中必不可少的物质。目前，哺乳动物中已确定有 11 种 17β-HSD 同工酶，它们的组织表达和底物转换模式各不相同。我们分析了人类和果蝇的 17β-HSD 10 型（17β-HSD10），已知后者在发育过程中至关重要。除了已知的羟基乙酰-CoA 脱氢酶、3α-OH 和 17β-OH 与性类固醇的活性之外，我们在此还证明了 17β-HSD10 的新活性。这两种变体都能氧化 C21 类固醇中的 20β-OH 和 21-OH 基团，并作为熊去氧胆酸或异熊去氧胆酸（也分别称为 7β-hydroxylithocholic acid 或 7β-hydroxyisolithocholic acid）的 7β-OH 脱氢酶发挥作用。此外，人类同源物还能氧化去氧胆酸（5β-胆酸，3α，7α-二醇）和胆酸（5β-胆酸）的 7α-OH 。这些新的底物特异性可以用基于同源大鼠晶体结构的同源模型来解释，该结构显示了一个宽阔的疏水裂隙，能够容纳不同方向的类固醇。这些特性表明，人类酶参与了糖皮质激素和孕激素的分解代谢，并参与了胆汁酸异构化。共聚焦显微镜和电子显微镜研究显示，人类的 17β-HSD10 定位于线粒体，而果蝇的 17β-HSD10 则显示出细胞质定位模式，这可能是由于人类 17β-HSD10 的 N 端序列差异造成的。
• Asymmetric reduction of 20-steroidal ketone: synthesis of corticosteroid derivatives containing the 20.alpha.-ol 21-al side chain
  作者：C. Arthur Han、Carl Monder

  DOI：10.1021/jo00347a045

  日期：1982.4
• Synthesis of new local anti-inflammatory thiosteroids based on antedrug concept
  作者：C Milioni、L Jung、B Koch

  DOI：10.1016/0223-5234(91)90137-c

  日期：1991.12

  The synthesis and the in vitro pharmacological evaluation of a number of topical corticosteroid derivatives designed on the basis of the antedrug concept are reported. Three series of compounds were synthesized in which sulfur-containing amino acids were incorporated to the steroidal structure in the 21 position. Compounds of series I are diesters of cystine with the 21-hydroxyl groups of the corticosteroids, while series II and III contain 21-amino and 21-thio corticosteroid derivatives, respectively. The new compounds were less potent than the parent corticosteroids in vitro. The 21-yl-[9-alpha-fluoro-11-beta,17-alpha-dihydroxy-16-alpha-methyl-1,4-pregnadiene-3,20-dione]-S-acetylamino cysteine 13 was the most interesting compound of the series and is now under further evaluation.
• US3944577A
  申请人：——

  公开号：US3944577A

  公开（公告）日：1976-03-16