(25R)-22-oxo-cholest-5-en-3β,16β,26β-triyl triacetate | 123748-72-1

• 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: (25R)-22-oxo-cholest-5-en-3β,16β,26β-triyl triacetate
• 英文别名: (25R)-22-oxocholest-5-ene-3β,16β,26-triyl triacetate；[(2R,6S)-6-[(3S,8S,9S,10R,13S,14S,16S,17R)-3,16-diacetyloxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxoheptyl] acetate
• CAS: 123748-72-1
• 化学式: C₃₃H₅₀O₇
• 分子量: 558.756
• InChiKey: ZZNKTXOEUUILFD-HOIBKBNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.22
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  95.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (25R)-22-oxo-cholest-5-en-3β,16β,26β-triyl triacetate 在 甲醇 、 氯化亚砜 、 三氟化硼乙醚 、 sodium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 22-oxo-B-homocholest-4-en-3β,16β,26-triyl triacetate
  参考文献：
  名称：

  薯蓣皂苷元和胆固醇中新型甾体肟和氮杂类甾体的制备及细胞毒性评价

  摘要：

  使用胆固醇和薯蓣皂苷元作为起始材料，我们设计了一种简单的方法，以减少步骤数制备一系列新型甾体肟及其具有四种侧链的氮杂高内酰胺类似物：胆甾烷、螺甾烷、22-氧代胆甾烷和 22 ,26-环氧胆甾烯。评估了这些产品对 MCF-7 乳腺癌细胞系的细胞毒活性。此外，针对外周血淋巴细胞测定了最活跃的化合物的选择性。化合物5、8和13被发现是最活跃的衍生物，其 IC 50值在低微摩尔范围 ( 7.9–9.5 µM) 和优异的选择性 (IC 50 > 100 µM) 对非肿瘤细胞系。

  DOI：

  10.1016/j.steroids.2022.109012
• 作为产物：
  描述：

  (22Ξ,25R)-3β-acetoxy-16α-chloro-22,26-epoxy-cholest-5-en-22-ol 在 溶剂黄146 作用下， 生成 (25R)-22-oxo-cholest-5-en-3β,16β,26β-triyl triacetate
  参考文献：
  名称：

  Molecular Rearrangements in the Steroids. XIII. The Non-reductive Scission of Rings E and F of the Steroidal Sapogenins

  摘要：

  DOI：

  10.1021/jo01113a001

文献信息

• Revision of the Absolute Configurations of Bethosides B and C and Their Aglycone
  作者：Victoria L. Challinor、Patricia Y. Hayes、Paul V. Bernhardt、William Kitching、Reginald P. Lehmann、James J. De Voss

  DOI：10.1021/jo2012797

  日期：2011.9.2

  The absolute stereochemistry of the steroidal saponins bethosides B and C was previously assigned as (22R,25R) on the basis of work that employed Horeau’s method. Our studies of helosides A and B created doubt about both the original assignment and consequently our conclusion that relied upon it. The absolute configurations of bethosides B and C are revised to (22S,25R) following X-ray crystallographic

  在采用Horeau方法的工作的基础上，以前将甾体皂苷B和C的甾体皂苷的绝对立体化学定为（22 R，25 R）。我们对螺旋藻A和B的研究使人们对原始分配以及因此得出的结论都产生了怀疑。在对它们的糖苷配基进行X射线晶体学分析后，山tho甙B和C的绝对构型被修订为（22 S，25 R）。据报道22 R和22 S糖苷配基的合成和全光谱表征有助于该系列皂苷的未来立体化学分配。
• 22‐Oxocholestanes SPGP4 and SPGP8: <i>in Silico</i> and <i>in Vitro</i> Study as Activators of Plant Growth Promotion
  作者：Luis Balbuena‐Hernández、Mariana Miranda‐Arámbula、Penélope Merino‐Montiel、Alan Carrasco‐Carballo、Jesús Sandoval‐Ramírez

  DOI：10.1002/cbdv.202201243

  日期：2023.5

  The 22‐oxocholestanes compounds have shown an outstanding plant growth promoting activity; they have similar bioactivity as brassinosteroids, so they are normally named as brassinosteroid analogs thinking that they also impact on the known receptor BRI1. However, in silico studies allow us to predict interactions with other receptors and thus it's possible to evaluate them, through receptors of gibberellins, auxins, jasmonates, strigolactones and the protein associated with the BRI1 gene. This article describes the bioactivity of structures SPGP4 and SPGP8 as plant growth‐promoting compounds. Both structures present coupling energies and interactions at the same level as epibrassinolide in the protein associated with BRI1 gene. Additionally, interactions through the auxin pathway and to strigolactone receptor were found using selected tests. In the rice lamina tilt, a higher effect was obtained when SPGP4 and SPGP8 were compared to epibrassinolide, although in a lesser level vis à vis to homobrassinolide. In the same way, when SPGP4 and SPGP8 were tested in the Growth Root Model an activity as strigonolactones was observed, enhancing the relationship between the main and secondary roots. However, the growth of coleptiles, when applying auxins, compounds SPGP4 and SPGP8 did not reach the same level as controls. In the tests associated to gibberellins and jasmonic acid, an increased bioactivity was observed, although this behavior was not reflected from the in silico study, possibly due to secondary signaling cascades. This work demonstrates that the 22‐oxocolestane compounds SPGP4 and SPGP8 could be used as plant growth hormones, promoting several pathways.

  摘要 22-氧代胆甾烷类化合物具有出色的植物生长促进活性；它们与铜生长激素具有相似的生物活性，因此通常被命名为铜生长激素类似物，认为它们也会对已知的受体 BRI1 产生影响。不过，通过硅学研究，我们可以预测它们与其他受体的相互作用，从而可以通过赤霉素、辅助素、茉莉酮、绞股蓝内酯的受体以及与 BRI1 基因相关的蛋白质对它们进行评估。本文介绍了 SPGP4 和 SPGP8 结构作为植物生长促进化合物的生物活性。这两种结构在与 BRI1 基因相关的蛋白质中的耦合能和相互作用水平与表没药内酯相同。此外，通过选定的测试，还发现了通过辅酶途径和与绞股蓝内酯受体的相互作用。在水稻叶片倾斜中，当 SPGP4 和 SPGP8 与表巴戟内酯相比时，获得了更高的效应，尽管与同型草内酯相比，其效应水平较低。同样，在生长根模型中对 SPGP4 和 SPGP8 进行测试时，也观察到了它们作为链格内酯的活性，从而增强了主根和次根之间的关系。不过，在使用辅酶、化合物 SPGP4 和 SPGP8 时，鞘翅目昆虫的生长并没有达到与对照组相同的水平。在与赤霉素和茉莉酸相关的测试中，观察到生物活性有所提高，但这一行为并未反映在硅学研究中，这可能是由于次级信号级联造成的。这项研究表明，22-氧代朱鹭烷化合物 SPGP4 和 SPGP8 可用作植物生长激素，促进多种途径的生长。
• Yahara, Shoji; Ohtsuka, Michiko (nee Ikeda); Nakano, Kimiko, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 7, p. 1802 - 1804
  作者：Yahara, Shoji、Ohtsuka, Michiko (nee Ikeda)、Nakano, Kimiko、Nohara, Toshihiro

  DOI：——

  日期：——