(R)-5-hydroxy-2-methoxy-3-(2,3-dihydro-2-methoxycarbonyl-4-methyl-3-oxofuran-2-yl)-4H-1-benzopyran-4-one | 1309045-45-1

• 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: (R)-5-hydroxy-2-methoxy-3-(2,3-dihydro-2-methoxycarbonyl-4-methyl-3-oxofuran-2-yl)-4H-1-benzopyran-4-one
• 英文别名: methyl (2R)-2-(5-hydroxy-2-methoxy-4-oxochromen-3-yl)-4-methyl-3-oxofuran-2-carboxylate
• CAS: 1309045-45-1
• 化学式: C₁₇H₁₄O₈
• 分子量: 346.293
• InChiKey: YASMNKRZQYEBRV-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  甲醇 、 xanthepinone 在 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 16.0h， 以1 mg的产率得到(R)-5-hydroxy-2-methoxy-3-(2,3-dihydro-2-methoxycarbonyl-4-methyl-3-oxofuran-2-yl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Chromone derivatives from the wood-decay fungus Rhizina sp. BCC 12292

  摘要：

  A new chromone derivative (1), together with the known oxepino[2,3-b] chromones, microsphaeropsones A (2) and B (3), and xanthopinone (4), was isolated from the wood-decay fungus Rhizina sp. BCC 12292. The structure of 1 was elucidated on the basis of NMR spectroscopic and mass spectrometry data. Transformation of 4 into 1 occurred when a solution of 4 in MeOH was treated with p-TsOH or silica gel, which strongly suggested that 1 may be an artifact formed during the processing of the extract. Compound 1 exhibited antimalarial activity with an IC(50) of 5.1 mu g/ml and cytotoxic activities against NCI-H187 and Vero cell lines with respective IC(50) of 6.4 and 1.6 mu g/ml. (C) 2010 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.phytol.2010.06.001

文献信息

• Chromone derivatives from the wood-decay fungus Rhizina sp. BCC 12292
  作者：Masahiko Isaka、Malipan Sappan、Patchanee Auncharoen、Prasert Srikitikulchai

  DOI：10.1016/j.phytol.2010.06.001

  日期：2010.9

  A new chromone derivative (1), together with the known oxepino[2,3-b] chromones, microsphaeropsones A (2) and B (3), and xanthopinone (4), was isolated from the wood-decay fungus Rhizina sp. BCC 12292. The structure of 1 was elucidated on the basis of NMR spectroscopic and mass spectrometry data. Transformation of 4 into 1 occurred when a solution of 4 in MeOH was treated with p-TsOH or silica gel, which strongly suggested that 1 may be an artifact formed during the processing of the extract. Compound 1 exhibited antimalarial activity with an IC(50) of 5.1 mu g/ml and cytotoxic activities against NCI-H187 and Vero cell lines with respective IC(50) of 6.4 and 1.6 mu g/ml. (C) 2010 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.