14-hydroxy-4-pregnene-3,20-dione | 16031-66-6

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: 14-hydroxy-4-pregnene-3,20-dione
• 英文别名: 14α-hydroxypregn-4-ene-3,20-dione；pregn-4-en-14α-ol-3,20-dione；14α-hydroxyprogesterone；14-hydroxy-progesterone；14-Hydroxyprogesterone；14-hydroxy-pregn-4-ene-3,20-dione；14alpha-Hydroxyprogesterone；(8R,9S,10R,13R,14R,17S)-17-acetyl-14-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 16031-66-6
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: UAMNQIUKJVUQMR-JRBOJVLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  14-hydroxy-4-pregnene-3,20-dione 生成 14-hydroxy-4-androstene-3,17-dione
  参考文献：
  名称：

  Microbiological Transformations of Steroids. XV. Tertiary Hydroxylation of Steroids by Fungi of the Order Mucorales^1,2

  摘要：

  DOI：

  10.1021/ja01546a047
• 作为产物：
  描述：

  progesterone 生成 14-hydroxy-4-pregnene-3,20-dione
  参考文献：
  名称：

  Nishikawa; Hagiwara, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 1256

  摘要：

  DOI：

文献信息

• Biotransformations of progesterone by Chlorella spp.
  作者：Antonino Pollio、Gabriele Pinto、Marina Della Greca、Antonio Fiorentino、Lucio Previtera

  DOI：10.1016/0031-9422(95)00996-5

  日期：1996.6

  Thirty-eight strains of Chlorella spp. were used as bioreactors on progesterone. Fourteen strains were ineffective whilst the others biotransformed the substrate. The observed bioreactions for progesterone were the hydroxylation, the reduction and the side-chain degradation. The kinds of biotransformation seem to fit the actual classification of the strains.

  三十八株小球藻。被用作黄体酮的生物反应器。十四株是无效的，而其他的生物转化了底物。观察到的黄体酮生物反应是羟基化、还原和侧链降解。生物转化的种类似乎符合菌株的实际分类。
• Microbial hydroxylation of steroids. Part 12. Hydroxylation of testosterone and related steroids by <i>Gnomonia</i><i>fructicola</i> ATCC 11430
  作者：Herbert L. Holland、Frances M. Brown、P. Chinna Chenchaiah、Michael J. Chernishenko、Shaheer H. Khan、J. Appa Rao

  DOI：10.1139/v89-044

  日期：1989.2.1

  The fungus Gnomoniafructicola ATCC 11430 hydroxylates testosterone at C-2β in 40–60% yield. The enzyme involved has been shown to be an inducible CO sensitive, cyanide insensitive oxygenase, with a requirement for theΔ⁴-3-ketosteroid substrate functionality. The use of 2α- and 2β-deuterium labelled substrates has shown that hydrogen loss from C-2 during 2β hydroxylation is isotope dependent and non-stereospecific. This is interpreted in terms of a Δ^2,4-dienolic enzyme-bound intermediate form of the substrate. Keywords: Gnomoniafructicola, hydroxylation, steroids, testosterone.

  真菌Gnomoniafructicola ATCC 11430以40-60%的产率在C-2β处对睾酮进行羟基化。所涉及的酶已被证明是一种可诱导的CO敏感、氰化物不敏感的氧化酶，需要Δ4-3-酮类固醇底物的功能性。使用2α-和2β-氘标记底物表明，在2β羟基化过程中，C-2处的氢损失是同位素依赖的，且不具有立体特异性。这被解释为底物的Δ2,4-二烯醇酶结合中间体形式。关键词：Gnomoniafructicola、羟基化、类固醇、睾酮。
• Microbial transformation of steroids: Contribution to 14α-hydroxylations
  作者：Shang-hui Hu、Gilles Genain、Robert Azerad

  DOI：10.1016/0039-128x(95)00006-c

  日期：1995.4

  The regioselective and stereoselective hydroxylation of steroids by fungal strains previously known for their hydroxylation capabilities, such as Thamnostylum (= Helicostylum) piriforme ATCC 8992, Mucor griseocyanus ATCC 1207a, Actinomucor elegans (= Mucor parasiticus) MMP 3122 (Mucorales), and Zygodesmus sp. ATCC 14716, was investigated with special interest for the 14 alpha-hydroxylation reaction

  以前以其羟基化能力而闻名的真菌菌株对类固醇的区域选择性和立体选择性羟基化，例如 Thamnostylum (= Helicostylum) piriforme ATCC 8992、Mucor griseocyanus ATCC 1207a、Actinomucor elegans (= Mucor parasiticus) MMP 3122 (MMP. ATCC 14716 对 14 α-羟基化反应特别感兴趣。初步筛选表明，其中一些微生物足以产生以下类固醇的 14 种 α-羟基化衍生物：孕酮、5 β-孕烷-3,20-二酮、3 β-羟基-5 β-孕烷-20 -one、3 beta-hydroxy-5 beta-17 (alpha H)-etianic酸甲酯、androst-4-ene-3,17-dione 和睾酮。大约 20 种代谢物已通过硅胶色谱法和半制备型反相 HPLC 分离和纯化。这些代谢物已通过
• Progesterone derivatives that bind to the digitalis receptor: synthesis of 14.beta.-hydroxyprogesterone: a novel steroid with positive inotropic activity
  作者：J. F. Templeton、V. P. Sashi Kumar、D. Cote、D. Bose、D. Elliott、R. S. Kim、F. S. LaBella

  DOI：10.1021/jm00391a038

  日期：1987.8

  e) is described. This novel steroid is about 10 times more potent than progesterone and one-tenth as potent as ouabagenin in an [3H]ouabain radioligand binding assay and is the first in a series of progesterone congeners that interact at the cardiac glycoside receptor both to possess the C/D cis ring junction and to enhance contractility of isolated cardiac tissue.

  描述了14-羟基-14β-孕-4-烯-3,20-二酮（14β-羟基孕酮）的合成。在[3H] ouabain放射性配体结合测定中，这种新型类固醇的效力比孕酮强约10倍，效力是哇巴genin的十分之一，并且是在孕激素糖苷受体相互作用的一系列孕激素同类物中第一个都具有C的类固醇/ D顺式环连接并增强离体心脏组织的收缩力。
• Biotransformation of progesterone by the green alga Chlorella emersonii C211-8h
  作者：Marina Della Greca、Antonio Fiorentino、Gabriele Pinto、Antonino Pollio、Lucio Previtera

  DOI：10.1016/0031-9422(95)00786-5

  日期：1996.4

  2β-Hydroxyprogesterone, 6β-hydroxyprogesterone, 9α-hydroxyprogesterone, 14α-hydroxyprogesterone, 16α-hydroxyprogesterone and 21-hydroxyprogesterone are the main bioproducts in the progesterone bioconversion by axenic cultures of Chlorella emersonii C211-8h. After 30 days 6β,9α-dihydroxyprogesterone, 6β,21-dihydroxyprogesterone and 16α,21-dihydroxyprogesterone are also formed. In acid conditions the reaction

  摘要 2β-羟基孕酮、6β-羟基孕酮、9α-羟基孕酮、14α-羟基孕酮、16α-羟基孕酮和21-羟基孕酮是Emersonii C211-Chlorella emersonii C211-孕酮生物转化的主要生物产物。30 天后，还会形成 6β,9α-二羟基孕酮、6β,21-二羟基孕酮和 16α,21-二羟基孕酮。在酸性条件下，反应较慢，生物制品中未发现 2β-羟基孕酮和 16α-羟基孕酮。在高盐条件下，产率通常较低，还会形成睾酮内酯。

表征谱图