pregna-4,16-diene-3,6,20-trione | 770712-08-8

• 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
• 英文名称: pregna-4,16-diene-3,6,20-trione
• 英文别名: pregnadiene-(4.16)-trione-(3.6.20)；Pregnadien-(4.16)-trion-(3.6.20)；(8R,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-2,7,8,9,11,12,14,15-octahydro-1H-cyclopenta[a]phenanthrene-3,6-dione
• CAS: 770712-08-8
• 化学式: C₂₁H₂₆O₃
• 分子量: 326.436
• InChiKey: ULMVGSYBZVBFJJ-RNHZEXENSA-N

物化性质

• 熔点：
  207-209 °C(Solv: methanol (67-56-1))
• 沸点：
  488.0±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  pregna-4,16-diene-3,6,20-trione 在 溶剂黄146 、 锌 作用下， 生成 5α-pregnane-3,6,20-trione
  参考文献：
  名称：

  Steroidal hormone intermediates and preparation of the same

  摘要：

  公开号：

  US02352848A1
• 作为产物：
  描述：

  3β-hydroxypregn-4,16-diene-6,20-dione 在 chromium(VI) oxide 作用下， 以 水 、 丙酮 为溶剂， 以80%的产率得到pregna-4,16-diene-3,6,20-trione
  参考文献：
  名称：

  New 5?-reductase inhibitors: In vitro and in vivo effects

  摘要：

  The enzyme 5 alpha-reductase is responsible for the conversion of testosterone (T) to its more potent androgen dihydrotestosterone (DHT). This steroid had been implicated in androgen-dependent diseases such as: benign prostatic hyperplasia. prostate cancer, acne and androgenic alopecia. The inhibition of 5 alpha-reductase enzyme offers a potentially useful treatment for these diseases.In this study, we report the synthesis and pharmacological evaluation of several new 3-substituted pregna-4, 16-diene-6, 20-dione derivatives. These compounds were prepared from the commercially available 16-dehydropregnenolone acetate. The biological activity of the new steroidal derivatives was determined in vivo as well as in vitro experiments.In vivo experiments, the anti-androgenic effect of the steroids was demonstrated by the decrease of the weight of the prostate gland of gonadectomized hamster treated with T plus finasteride or the new steroids. The IC50 value of these steroids was determined by measuring the conversion of radio labeled T to DHT.The results of this study carried out with 5 alpha-reductase enzyme from hamster and human prostate showed that four of the six steroidal derivatives (5, 7, 9, 10) exhibited much higher 5 alpha-reductase inhibitory activity, as indicated by the IC50 values than the presently used Proscar 3 (finasteride).The comparison of the weight of the hamster's prostate gland indicated that compound 5 had a comparable weight decrease as finasteride. The overall data of this study showed very clearly those compounds 5, 7, 9, 10 are good inhibitors for the 5 alpha-reductase enzyme. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.11.008

文献信息

• A novel and easy protocol to obtain 6-alkoxy-Δ4,6-diene-3-one derivatives from available sterols
  作者：Roxana Martínez-Pascual、Lidia Gabriela Felipe-Zaragoza、Miguel Ángel Peña-Rico、Alain Cruz-Nolasco、Lemuel Pérez-Picaso、Samuel Núñez-López、Adolfo López-Torres、Omar Viñas-Bravo

  DOI：10.1016/j.steroids.2023.109323

  日期：2023.12

  accessing 6-alkoxy-Δ4,6-diene-3-one derivatives. Such scaffolds were serendipitously obtained in the course of the study of the reaction of Δ4-3-keto steroids with catalytic amounts of iodine in refluxing methanol. A series of 6-methoxy and 6-ethoxy- Δ4,6-diene-3-ones were prepared from easily-available sterols in a two-step sequence; first, oxidation of sterols furnished the Δ4-3-keto steroids, which

  在此，我们报告了一种前所未有的有效方法来获取 6-烷氧基-Δ 4,6 -二烯-3-酮衍生物。这种支架是在研究 Δ 4 -3-酮类固醇与催化量的碘在回流甲醇中的反应过程中偶然获得的。一系列 6-甲氧基和 6-乙氧基-Δ 4,6-二烯-3-酮是由容易获得的甾醇以两步顺序制备的；首先将甾醇氧化得到Δ 4 -3-酮类固醇，然后以I 2为催化剂与乙醇或甲醇回流，得到一系列十种衍​​生物。此外，该方案对于在 C-6 处引入更大的碳链也有效。使用 SwissADME 工具预测合成化合物的药物似性特性。
• An efficient one-pot synthesis generating 4-ene-3,6-dione functionalised steroids from steroidal 5-en-3β-ols using a modified Jones oxidation methodology
  作者：A. Christy Hunter、Shelley-Marie Priest

  DOI：10.1016/j.steroids.2005.07.007

  日期：2006.1

  Steroids with 4-ene-3,6-dione functionality have application in natural product chemistry, as synthetic intermediates and as aromatase inhibitors. Here, we report a two-phase oxidation of a range of steroidal 5-en-3 beta-ols into corresponding 4-ene-3,6-diones using a modified Jones oxidation. The new reaction affords high yields (77-89%) of product in relatively short reaction times (1-2 h). The simplicity of this reaction gives significant advantages over previously reported methodologies. (c) 2005 Elsevier Inc. All rights reserved.
• Sapogenin transformation products and preparation of same
  申请人：PARKE DAVIS & CO

  公开号：US02352852A1

  公开（公告）日：1944-07-04