(2,4-dihydroxyphenyl)-[(2R,3R)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]methanone | 1449590-16-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (2,4-dihydroxyphenyl)-[(2R,3R)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]methanone
• CAS: 1449590-16-2
• 化学式: C₂₁H₁₆O₅
• 分子量: 348.355
• InChiKey: JAJPSCXLXGTUON-FPOVZHCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-羟基苯乙酸甲酯 在 4-二甲氨基吡啶 、 正丁基锂 、 对甲苯磺酰叠氮 、 辛酸铑 、 barium hydroxide octahydrate 、 palladium 10% on activated carbon 、 水 、 氢气 、 四丁基碘化铵 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2,4-dihydroxyphenyl)-[(2R,3R)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]methanone
  参考文献：
  名称：

  New chalcone dimers from Caesalpinia ferrea Mart act as potent inhibitors of DNA topoisomerase II

  摘要：

  New chalcone dimers, pauferrol B (2), and pauferrol C (3), were isolated from the stems of Caesalpinia ferrea Mart, and their structures were determined on the basis of 2D NMR spectroscopy. These new chalcone dimers showed potent inhibitory activities against human topoisomerase II and cell proliferation via the induction of apoptosis in human leukemia HL 60 cells. Absolute configurations of 2 and 3 were estimated by the comparison of CD spectra with a dihydrobenzofuran derivative 4, which was enantioselectively synthesized from 2-hydroxyphenyl acetic acid. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.028

文献信息

• New chalcone dimers from Caesalpinia ferrea Mart act as potent inhibitors of DNA topoisomerase II
  作者：Susumu Ohira、Kyouhei Takaya、Taichi Mitsui、Masahiro Kido、Kazuyuki Kakumoto、Ken-ichiro Hayashi、Atsuhito Kuboki、Hiroyuki Tani、Shogo Ikeda、Munekazu Iinuma、Yukihiro Akao、Hiroshi Nozaki

  DOI：10.1016/j.tetlet.2013.07.028

  日期：2013.9

  New chalcone dimers, pauferrol B (2), and pauferrol C (3), were isolated from the stems of Caesalpinia ferrea Mart, and their structures were determined on the basis of 2D NMR spectroscopy. These new chalcone dimers showed potent inhibitory activities against human topoisomerase II and cell proliferation via the induction of apoptosis in human leukemia HL 60 cells. Absolute configurations of 2 and 3 were estimated by the comparison of CD spectra with a dihydrobenzofuran derivative 4, which was enantioselectively synthesized from 2-hydroxyphenyl acetic acid. (C) 2013 Elsevier Ltd. All rights reserved.