3',5-dimethoxy-4'-(2R,3-dihydroxy-3-methylbutoxyl)-3'',3''-dimethylpyrano-(6,7)-isoflavone | 1292766-20-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3',5-dimethoxy-4'-(2R,3-dihydroxy-3-methylbutoxyl)-3'',3''-dimethylpyrano-(6,7)-isoflavone
• 英文别名: pierreione A；7-[4-[(2R)-2,3-dihydroxy-3-methylbutoxy]-3-methoxyphenyl]-5-methoxy-2,2-dimethylpyrano[3,2-g]chromen-6-one
• CAS: 1292766-20-1
• 化学式: C₂₇H₃₀O₈
• 分子量: 482.53
• InChiKey: XYVIHRJUIIUQSN-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3',5-dimethoxy-4'-(2R,3-dihydroxy-3-methylbutoxyl)-3'',3''-dimethylpyrano-(6,7)-isoflavone 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 氘代吡啶 作用下， 反应 2.0h， 生成 [(2R)-3-hydroxy-1-[2-methoxy-4-(5-methoxy-2,2-dimethyl-6-oxopyrano[3,2-g]chromen-7-yl)phenoxy]-3-methylbutan-2-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Pierreiones A−D, Solid Tumor Selective Pyranoisoflavones and Other Cytotoxic Constituents from Antheroporum pierrei

  摘要：

  Bioassay guided fractionation of a solid tumor selective extract of the leaves and twigs of Antheroporum pierrei acquired from the U.S. National Cancer Institute extract repository afforded four new pyranoisoflavones, pierreiones A-D (1-4), together with rotenone (5), 12a-hydroxyrotenone (6), and tephrosin (7). The structures of all new compounds were determined on the basis:of their spectroscopic data, and the absolute configuration oil Was assigned with the help of H-1 NMR analysis of its Mosher's ester derivatives. Compounds 1 and 5:77 accounted for the majority of the biological activity in terms of either cytotoxicity and/or selective toxicity to solid tumor cell lines. Pierreiones A (1) and B (2) demonstrated solid tumor selectivity With minimal cytotoxicity, while pierreione C(3) exhibited no activity.

  DOI：

  10.1021/np100763p

文献信息

• Pierreiones A−D, Solid Tumor Selective Pyranoisoflavones and Other Cytotoxic Constituents from <i>Antheroporum pierrei</i>
  作者：Song Gao、Ya-ming Xu、Frederick A. Valeriote、A. A. Leslie Gunatilaka

  DOI：10.1021/np100763p

  日期：2011.4.25

  Bioassay guided fractionation of a solid tumor selective extract of the leaves and twigs of Antheroporum pierrei acquired from the U.S. National Cancer Institute extract repository afforded four new pyranoisoflavones, pierreiones A-D (1-4), together with rotenone (5), 12a-hydroxyrotenone (6), and tephrosin (7). The structures of all new compounds were determined on the basis:of their spectroscopic data, and the absolute configuration oil Was assigned with the help of H-1 NMR analysis of its Mosher's ester derivatives. Compounds 1 and 5:77 accounted for the majority of the biological activity in terms of either cytotoxicity and/or selective toxicity to solid tumor cell lines. Pierreiones A (1) and B (2) demonstrated solid tumor selectivity With minimal cytotoxicity, while pierreione C(3) exhibited no activity.