(+/-)-1,2-dihydro-5-hydroxy-10-methoxy-2-[1-(hydroxymethyl)vinyl]-6H-furo[2,3-c]xanthen-6-one | 849818-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (+/-)-1,2-dihydro-5-hydroxy-10-methoxy-2-[1-(hydroxymethyl)vinyl]-6H-furo[2,3-c]xanthen-6-one
• 英文别名: 5-Hydroxy-2-(3-hydroxyprop-1-en-2-yl)-10-methoxy-1,2-dihydrofuro[2,3-c]xanthen-6-one
• CAS: 849818-39-9
• 化学式: C₁₉H₁₆O₆
• 分子量: 340.332
• InChiKey: AICOWJMFDSHONH-UHFFFAOYSA-N

物化性质

• 熔点：
  183-185 °C
• 沸点：
  597.4±50.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-1,2-dihydro-5-hydroxy-10-methoxy-2-[1-(hydroxymethyl)vinyl]-6H-furo[2,3-c]xanthen-6-one 在 吡啶 、 sodium hydroxide 、 四氧化锇 、 N-甲基吲哚酮 、 18-冠醚-6 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  Conformationally Restricted Analogues of Psorospermin:  Design, Synthesis, and Bioactivity of Natural-Product-Related Bisfuranoxanthones

  摘要：

  The antileukemic xanthone psorospermin is a topoisomerase II-dependent DNA alkylator in advanced preclinical. development. Efforts have been made to further understand the structural requirements of its mechanism of action through the synthesis of ring-constrained analogues, based on the skeleton of the bisfuranoxanthone natural products. Molecules were designed that contain the bisfuran and xanthone portions of naturally occurring psorofebrins, and molecular modeling was used to assess their DNA alkylating potential and to refine the structures. A short, diastereoselective synthetic process to access bisfuranoxanthones was developed, culminating in the first total synthesis of (+/-)-isohydroxypsorofebrin. Two compounds designed and synthesized were of particular interest, chlorohydrin 7 and epoxide 6, which are reactive analogues of the natural product isohydroxypsorofebrin. The chlorohydrin retains the psorospermin-like DNA alkylation characteristics despite its rigid structure and high innate affinity for DNA. Molecular modeling has been used to rationalize the increased activity of the chlorohydrin. The chlorohydrin and epoxide show increased cytotoxicity compared to isohydroxypsorofebrin against a range of human tumor cell lines.

  DOI：

  10.1021/jm049299c
• 作为产物：
  描述：

  1,3-dihydroxy-5-methoxy-9H-xanthen-9-one 在 N-碘代丁二酰亚胺 、 tris(dibenzylideneacetone)dipalladium (0) 、 四丁基氯化铵 、 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 93.0h， 生成 (+/-)-1,2-dihydro-5-hydroxy-10-methoxy-2-[1-(hydroxymethyl)vinyl]-6H-furo[2,3-c]xanthen-6-one
  参考文献：
  名称：

  Conformationally Restricted Analogues of Psorospermin:  Design, Synthesis, and Bioactivity of Natural-Product-Related Bisfuranoxanthones

  摘要：

  The antileukemic xanthone psorospermin is a topoisomerase II-dependent DNA alkylator in advanced preclinical. development. Efforts have been made to further understand the structural requirements of its mechanism of action through the synthesis of ring-constrained analogues, based on the skeleton of the bisfuranoxanthone natural products. Molecules were designed that contain the bisfuran and xanthone portions of naturally occurring psorofebrins, and molecular modeling was used to assess their DNA alkylating potential and to refine the structures. A short, diastereoselective synthetic process to access bisfuranoxanthones was developed, culminating in the first total synthesis of (+/-)-isohydroxypsorofebrin. Two compounds designed and synthesized were of particular interest, chlorohydrin 7 and epoxide 6, which are reactive analogues of the natural product isohydroxypsorofebrin. The chlorohydrin retains the psorospermin-like DNA alkylation characteristics despite its rigid structure and high innate affinity for DNA. Molecular modeling has been used to rationalize the increased activity of the chlorohydrin. The chlorohydrin and epoxide show increased cytotoxicity compared to isohydroxypsorofebrin against a range of human tumor cell lines.

  DOI：

  10.1021/jm049299c

文献信息

• Conformationally Restricted Analogues of Psorospermin:  Design, Synthesis, and Bioactivity of Natural-Product-Related Bisfuranoxanthones
  作者：Robert A. Heald、Thomas S. Dexheimer、Hariprasad Vankayalapati、Adam Siddiqui-Jain、Lajos Z. Szabo、Mary C. Gleason-Guzman、Laurence H. Hurley

  DOI：10.1021/jm049299c

  日期：2005.4.1

  The antileukemic xanthone psorospermin is a topoisomerase II-dependent DNA alkylator in advanced preclinical. development. Efforts have been made to further understand the structural requirements of its mechanism of action through the synthesis of ring-constrained analogues, based on the skeleton of the bisfuranoxanthone natural products. Molecules were designed that contain the bisfuran and xanthone portions of naturally occurring psorofebrins, and molecular modeling was used to assess their DNA alkylating potential and to refine the structures. A short, diastereoselective synthetic process to access bisfuranoxanthones was developed, culminating in the first total synthesis of (+/-)-isohydroxypsorofebrin. Two compounds designed and synthesized were of particular interest, chlorohydrin 7 and epoxide 6, which are reactive analogues of the natural product isohydroxypsorofebrin. The chlorohydrin retains the psorospermin-like DNA alkylation characteristics despite its rigid structure and high innate affinity for DNA. Molecular modeling has been used to rationalize the increased activity of the chlorohydrin. The chlorohydrin and epoxide show increased cytotoxicity compared to isohydroxypsorofebrin against a range of human tumor cell lines.