(25R)-spirostan-1,4,6-triene-3-one | 105119-49-1

• 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: (25R)-spirostan-1,4,6-triene-3-one
• 英文别名: (25R)-1,4,6-spirostatrien-3-one；(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17,19-triene-6,2'-oxane]-16-one
• CAS: 105119-49-1
• 化学式: C₂₇H₃₆O₃
• 分子量: 408.581
• InChiKey: LXKIKUPWWLNMTN-CLGLNXEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (25R)-spirostan-1,4,6-triene-3-one 在 乙酸酐 、 对甲苯磺酸 作用下， 生成 (25R)-3-acetoxy-1-methyl-19-nor-spirosta-1,3,5(10),6-tetraene
  参考文献：
  名称：

  Steroidal Sapogenins. XXXIII.¹ Aromatization Experiments in the Diosgenin Series

  摘要：

  DOI：

  10.1021/ja01637a062
• 作为产物：
  描述：

  2,6-dibromospirost-4-ene-3-one 在 2,4,6-三甲基吡啶 作用下， 生成 (25R)-spirostan-1,4,6-triene-3-one
  参考文献：
  名称：

  Steroidal Sapogenins. X.^1a Unsaturated 22-Isospirosten-3-ones^1b,2

  摘要：

  DOI：

  10.1021/ja01154a047

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。
• Epoxidation of Diosgenin, 25(R)-1,4,6-Spirostatrien-3-one and 25(R)-4,6-Spirostadien-3β-ol
  作者：Eunsook Ma、Jongwon Kim

  DOI：10.3390/81200886

  日期：——

  Upon treatment of 25(R)-spirost-5-en-3β-ol (diosgenin), 25(R)-1,4,6-spirostatrien-3-one and 25(R)-4,6-spirostadien-3β-ol with 30% H2O2 and 5% NaOH in methanol, diosgenin did not react, 25(R)-1,4,6-spirostatrien-3-one was converted to 25(R)-1α,2α-epoxy-4,6-spirostadien-3-one and 25(R)-4,6-spirostadien-3β-ol was oxidized to give a small amount of 25(R)-4,6-spirostadien-3-one, while most of the original starting material remained unchanged. On the other hand, reactions of diosgenin, 25(R)-1,4,6-spirostatrien-3-one and 25(R)-4,6-spirostadien-3β-ol with m-chloroperoxybenzoic acid in chloroform yielded 25(R)-5α,6α-epoxyspirostan-3β-ol, 25(R)-6α,7α-epoxy-1,4-spirostadien-3-one and 25(R)-4β,5β-epoxy-6-spirosten-3β-ol, respectively.

  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。
• 6-(4′-Aryl-1′,2′,3′-triazolyl)-spirostan-3,5-diols and 6-(4′-Aryl-1′,2′,3′-triazolyl)-7-hydroxyspirosta-1,4-dien-3-ones: Synthesis and analysis of their cytotoxicity
  作者：Maxim E. Mironov、Olga S. Oleshko、Mikhail A. Pokrovskii、Tatyana V. Rybalova、Vladislav K. Pechurov、Andrey G. Pokrovskii、Sergey V. Cheresis、Sergey V. Mishinov、Vyacheslav V. Stupak、Elvira E. Shults

  DOI：10.1016/j.steroids.2019.108460

  日期：2019.11

  potent anti-tumor agents from diosgenin, a series of C-6 derived 1,2,3-triazolyl derivatives were designed and synthesized by employing Cu(I) catalyzed Huisgen 1,3-dipolar cycloaddition reaction of novel azides - (22R,25R)-6β-azidospirostan-3β,5α-diol and 6β-azido-7α-hydroxyspirosta-1,4-dien-3-one with aryl(hetaryl)alkynes. All the derivatives were evaluated for cytotoxic activity by MTT assay against

  为了努力从薯os皂甙元开发有效的抗肿瘤药，利用新型叠氮化物的Cu（I）催化的Huisgen 1,3-偶极环加成反应设计并合成了一系列C-6衍生的1,2,3-三唑基衍生物-（22R，25R）-6β-叠氮螺螺-3-3,5α-二醇和6β-叠氮基-7α-羟基螺螺-1,4-dien-3-one与芳基（杂芳基）炔烃。通过MTT分析评估了所有衍生物对八种不同人类癌细胞系的细胞毒活性：T细胞白血病（CEM-13），人类单核细胞（U-937），乳腺（MDA-MB-231，BT-474），前列腺癌（DU-145）和胶质母细胞瘤（U-87MG，SNB-19，T98G）。这项研究的结果表明6-（4'-芳基-1'，2'，3'-三唑基）spirostan-3,5-二醇2、3、4、5和6具有潜在的细胞毒性潜力。相应的6-取代的7-羟基-1，4-spirostadien-3-ones对人类癌细胞的细胞毒性较小。化合物2、
• Synthesis of (25R)-ruscogenin-1-yl β-d-xylopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-β-d-fucopyranoside
  作者：Meizheng Liu、Biao Yu*、Xiangyang Wu、Yongzheng Hui*、Kwok-Pui Fung

  DOI：10.1016/s0008-6215(00)00244-5

  日期：2000.12

  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.
• Recoverable Pd/C catalyst mediated dehydrogenation of sterols and an improved synthesis of 1α-hydroxydehydroepiandrosterone
  作者：Yi-Zhen Yin、Chao Liu、Long-Qian Tang、Zhao-Peng Liu

  DOI：10.1016/j.steroids.2012.08.018

  日期：2012.11

  A novel recyclable Pd/C catalyst mediated dehydrogenation of sterols is developed. The conversion of sterols to 1,4,6-trien-3-ones is best achieved with Pd/C as a catalyst (10%) in the presence of six equivalents of allyl diethyl phosphate (ADP) and excess amount of sodium carbonate in DMF under vigorous reflux conditions. This transformation gives 17,17-ethylenedioxyandrost-1,4,6-trien-3-one in better yield than that of DDQ oxidation and thus provides an improved synthesis of 1 alpha-hydroxydehydroepiandrosterone from DHEA. (C) 2012 Elsevier Inc. All rights reserved.