24-ethylcholest-4,22-dien-3,6-dione | 50868-51-4

• 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: 24-ethylcholest-4,22-dien-3,6-dione
• 英文别名: stigmast-4,22(E)-dien-3,6-dione；stigmasta-4,22-diene-3,6-dione；stigmasta-4,22-dien-3,6-dione；sigmasta-4,22-dien-3,6-dione；stigmastadiene-(4.22t)-dione-(3.6)；Stigmastadien-(4.22t)-dion-(3.6)；(22e)-Stigmasta-4,22-diene-3,6-dione；(8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,6-dione
• CAS: 50868-51-4
• 化学式: C₂₉H₄₄O₂
• 分子量: 424.667
• InChiKey: XWHBTBBUPBKDBB-IZDHLYCQSA-N

物化性质

• 熔点：
  134-135 °C
• 沸点：
  522.9±20.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  24-ethylcholest-4,22-dien-3,6-dione 在 溶剂黄146 、 锌 作用下， 生成 22E,24R-stigmast-22-ene-3,6-dione
  参考文献：
  名称：

  Fernholz, Justus Liebigs Annalen der Chemie, 1934, vol. 508, p. 215,223

  摘要：

  DOI：
• 作为产物：
  描述：

  豆甾醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 以83%的产率得到24-ethylcholest-4,22-dien-3,6-dione
  参考文献：
  名称：

  一些甾体肟作为细胞毒剂的合成和评价：结构/活性研究（I）

  摘要：

  化合物的侧链在其生物学功能中起着重要作用。在我们的研究中，我们发现具有不同侧链和羟基氨基在环 A 和 B 上位置的羟基亚氨基类固醇衍生物对多种癌细胞类型显示出显着不同的细胞毒性。环 B 上的肟基团和环 A 或 B 上的羟基导致比其他结构基序更高的细胞毒性。此外，生物活性需要第 17 位的胆固醇型侧链。我们的研究结果提供了新的证据，表明化学结构与生物功能之间的关系。从研究中获得的信息可能有助于设计新型化疗药物。

  DOI：

  10.1016/j.steroids.2008.09.003

文献信息

• Synthesis and evaluation of some steroidal oximes as cytotoxic agents: Structure/activity studies (II)
  作者：Jianguo Cui、Lei Fan、Yanmin Huang、Yi Xin、Aimin Zhou

  DOI：10.1016/j.steroids.2009.07.009

  日期：2009.11

  side chain at position 17 is required for the biological activity of the compounds as we previously confirmed, elimination of the 4,5-double bond augmented the cytotoxic activity for the steroidal oximes. In addition, the presence of a hydroxy on 3- or 6-position of the steroidal nucleus resulted in a remarkable increase of cytotoxic activity. Our findings present more evidence showing the relationship

  从海洋海绵中分离出的羟氨基甾类化合物表现出多种生物学功能，包括细胞毒性和抗病毒功能。在这项研究中，我们合成了一系列在环A或B上具有不同官能团且在位置17处具有不同侧链的氢氧甾类衍生物，并分析了这些化合物对sk-Hep-1，H-292，PC-的细胞毒性3和Hey-1B癌细胞。我们的研究结果表明，尽管如我们先前所确认的，化合物17的胆固醇活性侧链对于化合物的生物学活性是必需的，但4,5双键的消除增强了甾体肟的细胞毒活性。另外，甾体核的3-或6-位上羟基的存在导致细胞毒性活性的显着增加。
• Facile Synthesis of Steroidal Δ⁴-3,6-Diones from Δ⁵-3-Ols using Pyridinium Chlorochromate
  作者：A. Nangia、A. Anthony

  DOI：10.1080/00397919608003608

  日期：1996.1

  Abstract Pyridinium chlorochromate (PCC) in dichloromethane under ambient conditions is found to oxidise steroidal Δ5-3-alcohols to Δ4-3,6-diketones in high yield.

  摘要 氯铬酸吡啶 (PCC) 在二氯甲烷中的环境条件下被发现可将甾体 Δ5-3-醇以高产率氧化为 Δ4-3,6-二酮。
• Stereospecific Oxidation of 3β-Hydroxysteroids by Persolvent Fermentation with<i>Pseudomonas</i>sp. ST-200
  作者：Aono Rikizo、Doukyu Noriyuki

  DOI：10.1271/bbb.60.1146

  日期：1996.1

  Pseudomonas sp. strain ST-200 isolated from a humus soil effectively oxidizes cholesterol dissolved in organic solvents but not that suspended in the growth medium. The organism does not assimilate cholesterol. This organism oxidized a variety of 5α- or 5-ene-sterols dissolved in organic solvent. First, the 3β-OH group was oxidized to a ketone group. The 3α-OH group was scarcely oxidized. Successively, C-6 position of 5-ene-steroids was hydroxylated, and a double bond of 5-ene-steroids was transferred from Δ5 to Δ 4. Then, the 6-OH group was oxidized to a ketone group. Persolvent fermentation with ST-200 would provide an effective, convenient, and stereospecific method to oxidize the C-3 and C-6 positions of steroids.

  从腐殖土中分离得到的Pseudomonas sp. 菌株ST-200能有效氧化溶解于有机溶剂中的胆固醇，但不能氧化悬浮于生长介质中的胆固醇。该菌株不吸收胆固醇，但能氧化多种溶解于有机溶剂的5α-或5-烯甾醇。首先，将3β-OH基团氧化为酮基，而3α-OH基团几乎不被氧化。接着，5-烯甾体的C-6位进行羟基化，5-烯甾体的双键从Δ5转移到Δ4。随后，6-OH基团被氧化为酮基。利用ST-200进行溶剂发酵可提供一种有效、便捷且具有立体选择性的方法，用于甾体化合物C-3和C-6位的氧化。
• Quantitative Structure Inter-Activity Relationship (QSInAR). Cytotoxicity Study of Some Hemisynthetic and Isolated Natural Steroids and Precursors on Human Fibrosarcoma Cells HT1080
  作者：Mihai V. Putz、Marius Lazea、Louis P. Sandjo

  DOI：10.3390/molecules16086603

  日期：——

  Combined experimental and quantitative structure inter-activity relationship (QSIAR) computation methods were advanced in order to establish the structural and mechanistic influences that steroids and triterpenes, either as newly synthesized or naturally isolated products, have on human HT1080 mammalian cancer cells. The main Hansch structural indicators such as hydrophobicity (LogP), polarizability (POL) and total energy (Etot) were considered and both the structure-projected as well as globally computed correlations were reported; while the inter-activity correlation of the global activity with those projected on structural information was revealed as equal to the direct structural-activity one for the trial sets of compounds, the prediction for the testing set of molecules reported even superior performances respecting those characteristic for the calibration set, validating therefore the present QSInAR models; accordingly, it follows that the LogP carries the most part of the cytotoxic signal, while POL has little influence on inhibiting tumor growth—A complementary behavior with their earlier known influence on genotoxic carcinogenesis. Regarding the newly hemisynthetic compounds it was found that stigmasta-4,22-dien-3-one is not adapted for cell membrane diffusion; it is recommended that aminocinnamyl chlorohydrate be further modified in order to acquire better steric influence, while aminocinnamyl-2,3,4,6-O-tétraacétyl-α-D-glucopyranoside was identified as being inhibited in the tumor cell by other molecular mechanisms–here not revealed–although it has a moderate-high anti-cancer structurally predicted activity.

  为了确定类固醇和三萜类化合物（无论是新合成的还是天然分离的产品）对人类 HT1080 哺乳动物癌细胞的结构和机理影响，我们采用了实验和定量结构间活性关系（QSIAR）计算相结合的方法。我们考虑了主要的 Hansch 结构指标，如疏水度 (LogP)、极化性 (POL) 和总能 (Etot)，并报告了结构预测和全局计算的相关性；全局活性与根据结构信息预测的活性之间的相关性与试验组化合物的直接结构-活性之间的相关性相同，而对测试组分子的预测报告甚至优于校准组的预测报告，从而验证了目前的 QSInAR 模型；因此，LogP 带有大部分细胞毒性信号，而 POL 对抑制肿瘤生长的影响很小--这与早先已知的 POL 对基因毒性致癌的影响是互补的。关于新的半合成化合物，发现石杉碱甲-4,22-二烯-3-酮不适合细胞膜扩散；此外，还发现氨肉桂基-2,3,4,6-O-tétraacétyl-α-D-吡喃葡萄糖苷可通过其他分子机制抑制肿瘤细胞--在此尚未揭示--尽管从结构上预测其具有中等偏上的抗癌活性。
• A facile and efficient synthesis of some (6E)-hydroximino-4-en-3-one steroids, steroidal oximes from Cinachyrella spp. sponges
  作者：Jianguo Cui、Liliang Huang、Lei Fan、Aimin Zhou

  DOI：10.1016/j.steroids.2007.10.007

  日期：2008.3

  Using beta-sitosterol as a starting material, (6E)-hydroximino-24-ethylcholest-4-en-3-one (1), a natural steroidal oxime from Cinachyrella alloclada and C. apion, was synthesized in four steps with a high overall yield. First, beta-sitosterol (5a) is transformed into the corresponding 24-ethylcholest-4-en-3,6-dione (6a) via oxidation with pyridinium. chlorochromate (PCC). Selective reduction of 6a by NaBH4 in the presence of CoCl2 gives 24-ethylcholest-4-en-3 beta-ol-6-one (7a). The reaction of 7a with hydroxylamine hydrochloride offers the oxime 8a and the oxidation of 8a by Jones reagent gives the target steroid 1. (6E)-Hydroximinocholest-4-en-3-one (2) and (6E)-hydroximino-24-ethylcholest-4,22-dien-3-one (4) were synthesized by a similar method. The cytotoxicity of the synthesized compounds against sk-Hep-1 (human liver carcinoma cell line), H-292 (human lung carcinoma cell line), PC-3 (human prostate carcinoma cell line) and Hey-1B (human ovarian carcinoma cell line) cells were investigated. The presence of a cholesterol-type side chain appears to be necessary for the biological activity. (C) 2007 Elsevier Inc. All rights reserved.