4-pregnene-3α,20(R)-diol | 60966-95-2

• 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: 4-pregnene-3α,20(R)-diol
• 英文别名: (3R,8S,9S,10R,13S,14S,17S)-17-[(1R)-1-hydroxyethyl]-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 60966-95-2
• 化学式: C₂₁H₃₄O₂
• 分子量: 318.5
• InChiKey: IBMZAHKIAAJREF-ONNYUIQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3α-hydroxy-17α-pregn-4-en-20-one 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 48.5h， 生成 4-pregnene-3α,20(R)-diol
  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

• Substrate Specificity and Inhibitor Sensitivity of Rabbit 20α-Hydroxysteroid Dehydrogenase
  作者：Satoshi Endo、Yuki Arai、Akira Hara、Yukio Kitade、Yasuo Bunai、Ossama El-Kabbani、Toshiyuki Matsunaga

  DOI：10.1248/bpb.b13-00342

  日期：——

  reduced the 3-keto group of only 5α-dihydrosteroids with 17β- or 20α/β-hydroxy group among 3-ketosteroids. In contrast, the enzyme reversibly and efficiently catalyzed the reduction of various 17- and 20-ketosteroids, including estrogen precursors (dehydroepiandrosterone, estrone and 5α-androstan-3β-ol-17-one) and tocolytic 5β-pregnane-3,20-dione. In addition to the progesterone inactivation, the formation

  在这项研究中，我们检查了兔20α-羟类固醇脱氢酶（AKR1C5）的底物特异性和抑制剂敏感性，该酶在孕激素失活终止妊娠中发挥作用。AKR1C5在3-酮类固醇中仅还原具有17β-或20α/β-羟基的5α-二氢类固醇的3-酮基。相比之下，该酶可逆地有效地催化各种17-和20-酮类固醇的还原，包括雌激素前体（脱氢表雄酮，雌酮和5α-雄烷-3β-ol-17-one）和解卵5β-孕烯3,20- dione。除孕激素失活外，AKR1C5的雌激素形成和生育溶性类固醇的代谢可能与其在兔分娩中的作用有关。AKR1C5还还原了各种非甾族羰基化合物，包括靛红，C型利钠肽受体和4-oxo-2-nonenal的拮抗剂，表明其在控制生物活性靛红和细胞毒性醛的解毒中的作用。AKR1C5被山茱emp醇和槲皮素等黄酮类化合物有效地和竞争性地抑制，表明其活性受摄入的黄酮类化合物的影响。
• Neurosteroid Analogues. 4. The Effect of Methyl Substitution at the C-5 and C-10 Positions of Neurosteroids on Electrophysiological Activity at GABA_A Receptors
  作者：Mingcheng Han、Charles F. Zorumski、Douglas F. Covey

  DOI：10.1021/jm960304p

  日期：1996.1.1

  A series of analogues of the neuroactive steroids 3 alpha-hydroxy-5 alpha-pregnan-20-one and 3 alpha-hydroxy-5 beta-pregnan-20-one were studied to elucidate the mode of binding of 5 alpha- and 5 beta-reduced steroids to steroid binding sites on GABA(A) receptors. Analogues which were either 3 alpha-hydroxy-20-ketosteroids or 3 alpha-hydroxysteroid-17 beta-carbonitriles and which contained various methyl group substitution patterns at C-5 and C-10 were prepared. Evaluations utilized whole-cell patch clamp electrophysiological methods carried out on cultured rat hippocampal neurons, and the results obtained with the rigid 17 beta-carbonitrile analogs were analyzed using molecular modeling methods. The molecular modeling results provide a rationale for the observation that the configuration of the hydroxyl group at C-3 is a greater determinant of anesthetic potency than the configuration of the A,B ring fusion at C-5. The electrophysiological results identify steric restrictions for the space that can be occupied in 5 alpha- and 5 beta-reduced steriod modulators of GABA(A) receptors in the regions of space proximate to the steroid C-5, C-10, and possibly C-4 positions. This information is useful for the development of nonsteroidal analogues that can modulate GABA(A) receptors via interactions at steroid binding sites.
• Synthesis and characteristics of allylic 4-pregnene-3,20-diols found in gonadal and breast tissues
  作者：J.P Wiebe、Vinod Dave、J.B Stothers

  DOI：10.1016/0039-128x(86)90095-4

  日期：1986.4

  Recently several allylic steroids have been found in gonadal and breast tissues. In order to establish their presence and identity in tissues and determine the possible biological properties, a method for the synthesis of 4-pregnene-3 alpha,20 alpha-diol, 4-pregnene-3 alpha, 20 beta-diol, 4-pregnene-3 beta,20 alpha-diol, and 4-pregnene-3 beta,20 beta-diol was developed using 4-pregnene-3,20-dione (progesterone) as substrate and freshly-prepared aluminum isopropoxide in isopropyl alcohol as reducing agent. The yields were about 19%, 30%, 13%, and 38% for the 3 alpha,20 alpha-, 3 alpha,20 beta-, 3 beta,20 alpha-, and 3 beta,20 beta-diols, respectively. The structures and stereochemistry of these diols were established using proton and carbon NMR spectroscopy and infrared and mass spectrometry.