(25R)-26-hydroxy-22-oxocholest-5-en-3β,16β-diyl diacetate | 123617-41-4

• 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: (25R)-26-hydroxy-22-oxocholest-5-en-3β,16β-diyl diacetate
• 英文别名: (25R)-26-hydroxy-22-oxocholest-5-ene-3β,16β-diyl diacetate；[(3S,8S,9S,10R,13S,14S,16S,17R)-16-acetyloxy-17-[(2S,6R)-7-hydroxy-6-methyl-3-oxoheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 123617-41-4
• 化学式: C₃₁H₄₈O₆
• 分子量: 516.719
• InChiKey: INUVWOFKWFJJFJ-WLMGVJRSSA-N

物化性质

• 熔点：
  208-210 °C
• 沸点：
  612.0±55.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (25R)-26-hydroxy-22-oxocholest-5-en-3β,16β-diyl diacetate 在 hydroxide 、 氢气 作用下， 生成 diosgenin
  参考文献：
  名称：

  Yahara, Shoji; Ohtsuka, Michiko (nee Ikeda); Nakano, Kimiko, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 7, p. 1802 - 1804

  摘要：

  DOI：
• 作为产物：
  描述：

  在 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 (25R)-26-hydroxy-22-oxocholest-5-en-3β,16β-diyl diacetate
  参考文献：
  名称：

  (26R)-26-羟基薯蓣皂苷元的立体选择性合成及其对大鼠卵巢功能调节的影响

  摘要：

  C-16 乙酰化 22,26-二氧胆甾烯衍生物立体选择性环化得到螺甾烷 E 和 F 环，在碱性条件下，仅产生 (26 R ) -26-羟基薯蓣皂苷元。实验和计算数据都支持形成单一的非对映异构体。还研究了薯蓣皂甙元和 (26 R )-26-羟基薯蓣皂甙元对大鼠卵巢的影响。

  DOI：

  10.1016/j.bioorg.2021.105189

文献信息

• Synthesis of 26-hydroxy-22-oxocholestanic frameworks from diosgenin and hecogenin and their in vitro antiproliferative and apoptotic activity on human cervical cancer CaSki cells
  作者：María A. Fernández-Herrera、Hugo López-Muñoz、José M.V. Hernández-Vázquez、Moisés López-Dávila、María L. Escobar-Sánchez、Luis Sánchez-Sánchez、B. Mario Pinto、Jesús Sandoval-Ramírez

  DOI：10.1016/j.bmc.2010.02.051

  日期：2010.4

  currently established. Herein, we report the synthesis and evaluation of two new 26-hydroxy-22-oxocholestanic steroids on cervical cancer CaSki cells. The title compounds were prepared from diosgenin and hecogenin in excellent yields. We determined their effect on cell proliferation, cell cycle, and cell death. The cytotoxic effect of the title compounds on CaSki and human lymphocytes was also evaluated

  某些类固醇化合物已显示出对几种肿瘤细胞系的抗增殖作用。然而，目前还没有确定它们对癌细胞的完全作用。在这里，我们报告了两种新的26-羟基-22-胆甾醇类固醇在宫颈癌CaSki细胞上的合成和评价。由薯os皂苷元和hecogenin以极高的收率制备标题化合物。我们确定了它们对细胞增殖，细胞周期和细胞死亡的影响。还评估了标题化合物对CaSki和人淋巴细胞的细胞毒性作用，表明主要的细胞死亡过程不是坏死。对淋巴细胞的无效作用表明它们没有细胞毒性。对凋亡小体的观察以及活性caspase-3表达的增加以及DNA的断裂证实了这种新的胆甾型骨架在肿瘤细胞中诱导了细胞凋亡。值得注意的是，它们对肿瘤细胞的抗增殖活性并不影响正常的子宫颈和外周血淋巴细胞的成纤维细胞的增殖潜能。标题化合物显示出选择性的抗肿瘤活性，因此可作为进一步优化的有希望的潜在候选对象。
• Preparation and cytotoxic evaluation of new steroidal oximes and aza-homosteroids from diosgenin and cholesterol
  作者：Thalía Lissette Mora-Medina、Roxana Martínez-Pascual、Miguel Ángel Peña-Rico、Omar Viñas-Bravo、Sara Montiel-Smith、Lemuel Pérez-Picaso、Hermenegilda Moreno-Díaz

  DOI：10.1016/j.steroids.2022.109012

  日期：2022.6

  Using cholesterol and diosgenin as starting materials, we have designed a straightforward methodology to prepare in a reduced number of steps a novel series of steroidal oximes and their aza-homolactam analogs with four types of side chains: cholestane, spirostane, 22-oxocholestane and 22,26-epoxycholestene. The products were evaluated for their cytotoxic activity against the MCF-7 breast cancer cell

  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。
• 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。
• 22-Oxocholestanes as plant growth promoters
  作者：Reyna Zeferino-Diaz、J. Ciciolil Hilario-Martinez、Maricela Rodriguez-Acosta、Jesus Sandoval-Ramirez、Maria A. Fernandez-Herrera

  DOI：10.1016/j.steroids.2015.03.005

  日期：2015.6

  The spirostanic steroidal side-chain of diosgenin and hecogenin was modified to produce 22-oxocholestane derivatives. This type of side-chain was obtained in good yields through a straightforward four-step pathway. These compounds show potent brassinosteroid-like growth promoting activity evaluated via the rice lamina joint inclination bioassay. This is the first report of steroidal skeletons bearing the 22-oxocholestane side-chain and preserving the basic structure (A-D rings) from their corresponding parent compounds acting as plant growth promoters. (C) 2015 Elsevier Inc. All rights reserved.
• Unexpected fragmentation of 16β-acetoxy-22-oxocholestanes on the action of methylenetriphenylphosphorane
  作者：Zuleykha R. Valiullina、Lidiya S. Khasanova、Natalya K. Selezneva、Fanuza A. Gimalova、Kasimir K. Pivnitsky、Mansur S. Miftakhov

  DOI：10.1016/j.mencom.2014.09.008

  日期：2014.9

  Treatment of 16 beta-acetoxy-22-oxocholestanes with methylenetriphenylphosphorane results in the cleavage of C-22-C-23 bond and formation of bisnorcholanic (22 -> 16)-lactones. The analogous fragmentation also partially proceeds on (BuOK)-O-t action.