1α,2α-epoxy-(25R)-spirostan-4,6-dien-3-one | 201858-25-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1α,2α-epoxy-(25R)-spirostan-4,6-dien-3-one
• 英文别名: (25R)-1α,2α-epoxy-4,6-spirostadien-3-one；(20S,22R,25R)-1α,2α-epoxyspirosta-4,6-dien-3-one；(1R,2R)-1,2-epoxy-(25R)-spirostan-4,6-dien-3-one；(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14R,16R)-5',7,9,13-tetramethylspiro[5,15-dioxahexacyclo[10.9.0.02,9.04,8.013,19.014,16]henicosa-18,20-diene-6,2'-oxane]-17-one
• CAS: 201858-25-5
• 化学式: C₂₇H₃₆O₄
• 分子量: 424.58
• InChiKey: KPGSWGUICDTANC-LOQZNTTQSA-N

物化性质

• 熔点：
  219.2-220.8 °C
• 沸点：
  567.4±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1α,2α-epoxy-(25R)-spirostan-4,6-dien-3-one 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以53%的产率得到(20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene
  参考文献：
  名称：

  Synthesis of (25R)-ruscogenin-1-yl β-d-xylopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-β-d-fucopyranoside

  摘要：

  The synthesis of (25R)-ruscogenin-1-yl beta -D-xylopyranosyl-(1 --> 3)-[beta -D-glucopyranosyl-(1 --> 2)]-beta -D-fucopyranoside, a saponin from the tuber of Liriope muscari (Decne.) Bailey, is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00244-5
• 作为产物：
  描述：

  薯蓣皂素 在 sodium hydroxide 、 双氧水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 46.0h， 生成 1α,2α-epoxy-(25R)-spirostan-4,6-dien-3-one
  参考文献：
  名称：

  Epoxidation of Diosgenin, 25(R)-1,4,6-Spirostatrien-3-one and 25(R)-4,6-Spirostadien-3β-ol

  摘要：

  在甲醇中使用30% H2O2和5% NaOH处理25(R)-螺甾-5-烯-3β-醇（薯蓣皂苷元）、25(R)-1,4,6-螺甾三烯-3-酮和25(R)-4,6-螺甾二烯-3β-醇时，薯蓣皂苷元未发生反应，25(R)-1,4,6-螺甾三烯-3-酮转化为25(R)-1α,2α-环氧-4,6-螺甾二烯-3-酮，而25(R)-4,6-螺甾二烯-3β-醇被氧化生成少量25(R)-4,6-螺甾二烯-3-酮，大部分原始起始物质保持不变。另一方面，薯蓣皂苷元、25(R)-1,4,6-螺甾三烯-3-酮和25(R)-4,6-螺甾二烯-3β-醇与间氯过氧苯甲酸在氯仿中的反应分别得到25(R)-5α,6α-环氧螺甾烷-3β-醇、25(R)-6α,7α-环氧-1,4-螺甾二烯-3-酮和25(R)-4β,5β-环氧-6-螺甾烯-3β-醇。

  DOI：

  10.3390/81200886

文献信息

• Synthesis and cytotoxic activities of 2-substituted (25R)-spirostan-1,4,6-triene-3-ones via ring-opening/elimination and ‘click’ strategy
  作者：Xiao-Feng Lu、Zheng Yang、Nian-Yu Huang、Hai-Bo He、Wei-Qiao Deng、Kun Zou

  DOI：10.1016/j.bmcl.2015.06.028

  日期：2015.9

  more effective antitumor steroidal drugs, we synthesized a library including twenty-two novel cytotoxic 2-alkyloxyl substituted (25R)-spirostan-1,4,6-triene-3-ones and corresponding 1,2,3-triazoles through an abnormal monoepoxide ring-opening/elimination and ‘click’ reactions. After the cytotoxic evaluations against HepG2, Caski and HeLa cell lines, three steroidal triazoles 5b, 5f and 5m in this library

  为了开发更有效的抗肿瘤甾体药物，我们合成了一个文库，该文库通过以下方法合成了一个库，该库包括二十二种新的细胞毒性的2-烷氧基取代的（25 R）-spirostan-1,4,6-三烯-3-酮和相应的1,2,3-三唑异常的单环开环/消除和“喀哒”反应。在对HepG2，Caski和HeLa细胞系进行细胞毒性评估后，发现该文库中的三种甾体三唑5b，5f和5m具有对Caski细胞的强抗增殖作用，其半抑制浓度（IC 50）为9.4-11.8。微米 高效，简单的方法是轻松制备抗肿瘤甾体三唑的诱人之处。
• Preparations of vitamin D analogs, spirostanols and furostanols from diosgenin and their cytotoxic activities
  作者：Hong-Ji Quan、Jyunichi Koyanagi、Fusao Komada、Setsuo Saito

  DOI：10.1016/j.ejmech.2005.02.003

  日期：2005.7

  Vitamin D analogs 12 and 13 having a spiro ring in the side chain, various spirostanols 18-21, 26, 27, 29 and 37, and furostanols 34-36 having SCN and SeCN groups at the 26 position were prepared from diosgenin 1 via (20S,22R,25R)-spirost-1 alpha,2 alpha-epoxy-4,6-dien-3-one 19 as a key intermediate. The cytotoxic activities of these derivatives as well as 1 on scarcely P-gp-expressed HCT 116 cells and P-gp-overexpressed Hep G2 cells were examined by MTT assay. Furostanols 34 (IC50 value: 4.9 +/- 0.3 mu M) and 36 (IC50 value: 1.3 +/- 0.2 mu M) exhibited marked cytotoxic effects on HCT 116 cells, and spirostanol 29 (IC50 value: 2.4 0.8 mu M) and furostanol 36 (IC50 value: 2.8 +/- 0.4 mu M) on Hep G2 cells. Furthermore, the effects of vitamin D analog 12, spirostanol 26 and furostanol 36 on apoptosis-signaling pathways were investigated. Compounds 12 and 26 overexpressed p53 and Bax mRNAs, while compound 36 overexpressed only Bax mRNA. (c) 2005 Elsevier SAS. All rights reserved.
• First total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside, an ophiopogonis saponin from the tuber of Liriope muscari (Decne.)
  作者：Meizheng Liu、Biao Yu、Yongzheng Hui

  DOI：10.1016/s0040-4039(97)10536-6

  日期：1998.1

  The first total synthesis of 25(R)-ruscogenin-1-yl beta-D-xylopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->)]-beta-D-fucopyranoside (1), an Ophiopogonis saponin with strong anti-inflammatory and immunopharmacological activities from the tuber of Liriope musrari (Decne.), is described. The glycosylaton of a highly hindered alcohol by Schmidt's "inverse procedure" is demonstrated. (C) 1997 Elsevier Science Ltd. All rights reserved.