ajugasterone C-2,3,20,22-diacetonide | 84028-24-0

• 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: ajugasterone C-2,3,20,22-diacetonide
• 英文别名: Ajugasterone C 2,320,22-Diacetonide；(1R,2R,4S,8R,10R,14S,17S,18R,20R)-14,20-dihydroxy-2,6,6,18-tetramethyl-17-[(4R,5R)-2,2,4-trimethyl-5-(3-methylbutyl)-1,3-dioxolan-4-yl]-5,7-dioxapentacyclo[11.7.0.02,10.04,8.014,18]icos-12-en-11-one
• CAS: 84028-24-0
• 化学式: C₃₃H₅₂O₇
• 分子量: 560.772
• InChiKey: PAYRGVCZJJHSFE-MPQXGJTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ajugasterone C-2,3,20,22-diacetonide 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium tetrahydroborate 作用下， 生成 (5R,6S,9R,10S,11R,13R,14S,17S)-6,14-dihydroxy-17-((4R,5R)-5-isopentyl-2,2,4-trimethyl-1,3-dioxolan-4-yl)-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-2,3,11-triyl tribenzoate
  参考文献：
  名称：

  Additivity relation in the amplitudes of exciton-split circular dichroism curves arising from interactions between different chromophores and its application in structural studies

  摘要：

  DOI：

  10.1021/ja00339a031
• 作为产物：
  描述：

  筋骨草甾酮 C 、 丙酮 在 molybdophosphoric acid hydrate 作用下， 反应 0.42h， 以62.4%的产率得到ajugasterone C-2,3,20,22-diacetonide
  参考文献：
  名称：

  角鲨烯化的纳米颗粒前体药物佐剂抗肿瘤药11α-羟基蜕皮甾类2,3-乙酰丙酮类药物作为抗阿霉素和紫杉醇的细胞保护剂

  摘要：

  几种蜕皮类固醇丙酮化物可作为针对各种癌细胞系的辅助化学增敏剂，它们可通过与角鲨烯的可水解缀合配制成自组装的纳米颗粒（NP）前药。在血流中，这种角鲨烯化的纳米颗粒会溶解到低密度脂蛋白（LDL）中，从而可以靶向含有高水平LDL受体的组织。在这项工作中，金刚烷酮C 2,3; 20,22-二烯酮（3）和11α-羟基孕甾酮2,3-丙酮（4）被角鲨烯化，以获得两种新的蜕皮甾类前药（6 和 7）及其纳米组件（6 NP 和 7 NP）。的完整NMR信号分配6 和 7已实现。化合物的相互作用3 和 4通过Chou-Talalay方法研究了化疗药物的使用。复合3在多药耐药性淋巴瘤细胞系中显示出与阿霉素的强协同作用。相反，其纳米组装6 NP明显降低了阿霉素对这些MDR细胞的细胞毒性，强烈表明在前药胞吞后，至少2,3-丙酮化物基团被溶酶体的酸性pH裂解。此外，复合4 与紫杉醇对MCF-7细胞及其纳米物质具有强拮抗作用

  DOI：

  10.3389/fphar.2020.552088

文献信息

• Significant Activity of Ecdysteroids on the Resistance to Doxorubicin in Mammalian Cancer Cells Expressing the Human ABCB1 Transporter
  作者：Ana Martins、Noémi Tóth、Attila Ványolós、Zoltán Béni、István Zupkó、József Molnár、Mária Báthori、Attila Hunyadi

  DOI：10.1021/jm300424n

  日期：2012.6.14

  Multidrug resistance (MDR) is a major cause of failure of cancer chemotherapy. Fifty-eight ecdysteroids, herbal analogues of the insect molting hormone and their semisynthetic derivatives, were tested for their activity against L5178 mouse T-cell lymphoma cells (non-MDR) and their subcell line transfected with pHa MDR1/A retrovirus overexpressing the human ABCB1 efflux pump (MDR cell line). The compounds showed very low antiproliferative activities but modulated the efflux of rhodamine 123 mediated by the ABCB1 transporter. Roughly depending on the polarity, mild to strong synergism or antagonism was observed by combining ecdysteroids with doxorubicin, and specific structure-activity relationships were also found. Our results show the effect of ecdysteroids on MDR cancer cells for the first time. Less polar derivatives may serve as valuable leads toward a potent and safe resistance modulator. Biological significance of the resistance-increasing activity of the most abundant phytoecdysteroids including 20-hydroxyecdysone is yet to be clarified.
• Additivity relation in the amplitudes of exciton-split circular dichroism curves arising from interactions between different chromophores and its application in structural studies
  作者：Richard J. Stonard、Diane A. Trainor、Munehiro Nakatani、Koji Nakanishi

  DOI：10.1021/ja00339a031

  日期：1983.1
• Squalenoylated Nanoparticle Pro-Drugs of Adjuvant Antitumor 11α-Hydroxyecdysteroid 2,3-Acetonides Act as Cytoprotective Agents Against Doxorubicin and Paclitaxel
  作者：Máté Vágvölgyi、Péter Bélteky、Dóra Bogdán、Márta Nové、Gabriella Spengler、Ahmed D. Latif、István Zupkó、Tamás Gáti、Gábor Tóth、Zoltán Kónya、Attila Hunyadi

  DOI：10.3389/fphar.2020.552088

  日期：——

  In this work, ajugasterone C 2,3;20,22-diacetonide (3) and 11α-hydroxypoststerone 2,3-acetonide (4) were squalenoylated to obtain two new ecdysteroid pro-drugs (6 and 7) and their nano-assemblies (6NP and 7NP). A complete NMR signal assignment of 6 and 7 was achieved. Interaction of compounds 3 and 4 with chemotherapeutics was studied by the Chou-Talalay method. Compound 3 showed strong synergism with

  几种蜕皮类固醇丙酮化物可作为针对各种癌细胞系的辅助化学增敏剂，它们可通过与角鲨烯的可水解缀合配制成自组装的纳米颗粒（NP）前药。在血流中，这种角鲨烯化的纳米颗粒会溶解到低密度脂蛋白（LDL）中，从而可以靶向含有高水平LDL受体的组织。在这项工作中，金刚烷酮C 2,3; 20,22-二烯酮（3）和11α-羟基孕甾酮2,3-丙酮（4）被角鲨烯化，以获得两种新的蜕皮甾类前药（6 和 7）及其纳米组件（6 NP 和 7 NP）。的完整NMR信号分配6 和 7已实现。化合物的相互作用3 和 4通过Chou-Talalay方法研究了化疗药物的使用。复合3在多药耐药性淋巴瘤细胞系中显示出与阿霉素的强协同作用。相反，其纳米组装6 NP明显降低了阿霉素对这些MDR细胞的细胞毒性，强烈表明在前药胞吞后，至少2,3-丙酮化物基团被溶酶体的酸性pH裂解。此外，复合4 与紫杉醇对MCF-7细胞及其纳米物质具有强拮抗作用