| 1227475-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• CAS: 1227475-81-1
• 化学式: C₂₇H₂₃BrO₇
• 分子量: 539.379
• InChiKey: GJFFMDCCIZRVBK-SZUBIPLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  在 氨 、 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 36.0h， 生成 (1R,2R,3S,3aR,8bS)-3a-(4-bromophenyl)-1,8b-dihydroxy-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
  参考文献：
  名称：

  Novel Flavaglines Displaying Improved Cytotoxicity

  摘要：

  Novel flavagline analogues were synthesized and examined with respect to their cytotoxicity Structural features critical to the potential of this class of anticancer natural products wet e unraveled We demonstrated, in particular, that the introduction of substituants at C-2 has a deleterious effect on multidrug resistance Replacement of the hydroxy at C-1 by an aminoformyl with the opposite configuration enhances the cytotoxicity and led to a compound that reduces tumors growth in an allograft model at nontoxic doses

  DOI：

  10.1021/jm101318b
• 作为产物：
  描述：

  methyl 2-(4-bromophenyl)-6,8-dimethoxy-5-hydroxy-2,5-methano-10-oxo-2,3,4,5-tetrahydro-1-benzoxepin-4-carboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  仿生动力学拆分：Aglain 酮的高度对映和非对映选择性转移氢化以获得黄黄素天然产物

  摘要：

  我们之前报道了 aglains (+)-ponapensin 和 (+)-elliptifoline 的不对称合成和绝对构型分配，并提出了一种生物合成动力学拆分过程来生产对映体罗卡酰胺和 aglains。在此，我们报告了一种仿生方法，通过利用对映选择性转移氢化作用的桥酮的动力学拆分来合成对映体富集的阿格兰和罗卡酰胺。该方法已用于合成和确认嘧啶酮罗卡酰胺 (+)-aglaistatin 和 (−)-aglaroxin C 的绝对立体化学。此外，还分析了每种代谢物的对映体和外消旋体的热休克反应抑制、细胞毒性。和翻译抑制。

  DOI：

  10.1021/ja511728b

文献信息

• Synthetic Analogue of Rocaglaol Displays a Potent and Selective Cytotoxicity in Cancer Cells: Involvement of Apoptosis Inducing Factor and Caspase-12
  作者：Frédéric Thuaud、Yohann Bernard、Gülen Türkeri、Ronan Dirr、Geneviève Aubert、Thierry Cresteil、Aurélie Baguet、Catherine Tomasetto、Yuri Svitkin、Nahum Sonenberg、Canan G. Nebigil、Laurent Désaubry

  DOI：10.1021/jm900365v

  日期：2009.8.27

  Flavaglines constitute a family of natural anticancer compounds. We present here 3 (FL3), the first synthetic flavagline that inhibits cell proliferation and viability (IC50 approximate to 1 nM) at lower doses than did the parent compound, racemic rocaglaol. Compound 3 enhanced doxorubicin cytotoxicity in HepG2 cells and retained its potency against. adriamycin-resistant cell lines without inducing cardiomyocyte toxicity. Compound 3 induced apoptosis of HL60 and Hela cells by triggering the translocation of Apoptosis Inducing Factor (AIF) and caspase-12 to the nucleus. A fluorescent conjugate of 3 accumulated ill endoplasmic reticulum (ER), suggesting that flavaglines bind to their target in the ER. where it triggers a cascade of events that leads to the translocation of AIF and caspase-12 to the nucleus and probably inhibition of eIF4A. Our studies highlight structural features critical to their antineoplastic potential and suggest that these compounds would retain their activity in cells refractory to caspase activation.