(25R)-26-hydroxy-12,22-dioxo-5α-cholestan-3β,16β-diyl diacetate | 1228298-02-9

• 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-12,22-dioxo-5α-cholestan-3β,16β-diyl diacetate
• 英文别名: [(3S,5S,8R,9S,10S,13S,14S,16S,17R)-16-acetyloxy-17-[(2S,6R)-7-hydroxy-6-methyl-3-oxoheptan-2-yl]-10,13-dimethyl-12-oxo-1,2,3,4,5,6,7,8,9,11,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1228298-02-9
• 化学式: C₃₁H₄₈O₇
• 分子量: 532.718
• InChiKey: PJEIZYOGVHHVCL-KINUGENKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (25R)-26-hydroxy-12,22-dioxo-5α-cholestan-3β,16β-diyl diacetate 在 4-二甲氨基吡啶 、 溶剂黄146 、 sodium iodide 、 锌 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 31.75h， 生成 12,22-dioxo-5α-cholestane-3β,16β-diyl diacetate
  参考文献：
  名称：

  22-Oxocholestanes as plant growth promoters

  摘要：

  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.

  DOI：

  10.1016/j.steroids.2015.03.005
• 作为产物：
  描述：

  乙酸酐 、 海柯吉宁 在 三氟化硼乙醚 、 水 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到(25R)-26-hydroxy-12,22-dioxo-5α-cholestan-3β,16β-diyl diacetate
  参考文献：
  名称：

  薯gen皂苷元和hecogenin合成26-羟基-22-胆甾型骨架及其对人宫颈癌CaSki细胞的体外抗增殖和凋亡活性

  摘要：

  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。

  DOI：

  10.1016/j.bmc.2010.02.051

文献信息

• Synthesis of the steroidal glycoside (25R)-3β,16β-diacetoxy-12,22-dioxo-5α-cholestan-26-yl β-d-glucopyranoside and its anti-cancer properties on cervicouterine HeLa, CaSki, and ViBo cells
  作者：María A. Fernández-Herrera、Sankar Mohan、Hugo López-Muñoz、José M.V. Hernández-Vázquez、Esmeralda Pérez-Cervantes、María L. Escobar-Sánchez、Luis Sánchez-Sánchez、Ignacio Regla、B. Mario Pinto、Jesús Sandoval-Ramírez

  DOI：10.1016/j.ejmech.2010.07.051

  日期：2010.11

  The synthesis of the new glycoside (25R)-3 beta,16 beta-diacetoxy-12,22-dioxo-5 alpha-cholestan-26-yl beta-D-glucopyranoside starting from hecogenin is described. This compound showed anti-cancer activity against cervicouterine cancer cells HeLa. CaSki and ViBo in the micromolar range. Its effect on cell proliferation, cell cycle and cell death is also described. The cytotoxic effect of the title compound on HeLa, CaSki and ViBo cells and human lymphocytes was evaluated through the LDH released in the culture supernatant, indicating that the main cell death process is not necrosis; the null effect on lymphocytes implies that it is not cytotoxic. The ability of this novel glycoside to induce apoptosis was investigated; several apoptosis events like chromatin condensation, formation of apoptotic bodies, as well as the increase in the expression of active caspase-3 and the fragmentation of DNA confirmed that the compound induced apoptosis in cervicouterine cancer cells. Significantly, the antiproliferative activity on tumor cells did not affect the proliferative potential of normal fibroblasts from cervix and peripheral blood lymphocytes. The glycoside showed selective antitumor activity and greater antiproliferative activity than its aglycon; it therefore serves as a promising lead candidate for further optimization. (C) 2010 Elsevier Masson SAS. All rights reserved.