(R)-tetrahydro-4,4-dimethyl-2-oxo-3-furanyl (S)-2-(5-methyl-9-oxo-9H-xanthen-4-yl)propanoate | 134940-31-1

• 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)-tetrahydro-4,4-dimethyl-2-oxo-3-furanyl (S)-2-(5-methyl-9-oxo-9H-xanthen-4-yl)propanoate
• 英文别名: [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (2S)-2-(5-methyl-9-oxoxanthen-4-yl)propanoate
• CAS: 134940-31-1
• 化学式: C₂₃H₂₂O₆
• 分子量: 394.424
• InChiKey: ASHPRDSRKKPCIN-RBZFPXEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  82.81
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-tetrahydro-4,4-dimethyl-2-oxo-3-furanyl (S)-2-(5-methyl-9-oxo-9H-xanthen-4-yl)propanoate 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 生成 (S)-(+)-2-(5-methyl-9-oxo-9H-xanthen-4-yl)propionic acid
  参考文献：
  名称：

  Potential antitumor agents. 63. Structure-activity relationships for side-chain analogs of the colon 38 active agent 9-oxo-9H-xanthene-4-acetic acid

  摘要：

  A series of 16 analogues of the solid tumor active compound 9-oxo-9H-xanthene-4-acetic acid (XAA), with variations in the acetic acid side chain, have been prepared and evaluated for their ability to cause early haemorrhagic necrosis of colon 38 tumors in mice. The results extend the previous SAR for this class and confirm the necessity for a carboxylic acid group in a fixed disposition with respect to the xanthenone chromophore. None of the compounds showed superior potency to XAA itself, with virtually all alterations in the nature of the anionic center or its geometry with respect to the chromophore greatly reducing or abolishing activity. However, alpha-methylation of the side chain was permissible, and the two enantiomers of 5-methyl-alpha-methyl-XAA were separated and tested. Both were active, but the S-(+) enantiomer was much more dose-potent than the R-(-) enantiomer, in both the in vivo tumor necrosis assay and an in vitro assay measuring the stimulation of nitric oxide production by macrophages. This suggests that the enantiomers have different intrinsic activities, rather than differing in their vivo metabolism.

  DOI：

  10.1021/jm00113a027
• 作为产物：
  描述：

  2-(2-hydroxyphenyl)propanoic acid disodium salt 在 1-甲基吡咯烷 、 草酰氯 、 硫酸 、 三(3,6-二氧杂庚基)胺 、 copper(l) chloride 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 13.67h， 生成 (R)-tetrahydro-4,4-dimethyl-2-oxo-3-furanyl (S)-2-(5-methyl-9-oxo-9H-xanthen-4-yl)propanoate
  参考文献：
  名称：

  Potential antitumor agents. 63. Structure-activity relationships for side-chain analogs of the colon 38 active agent 9-oxo-9H-xanthene-4-acetic acid

  摘要：

  A series of 16 analogues of the solid tumor active compound 9-oxo-9H-xanthene-4-acetic acid (XAA), with variations in the acetic acid side chain, have been prepared and evaluated for their ability to cause early haemorrhagic necrosis of colon 38 tumors in mice. The results extend the previous SAR for this class and confirm the necessity for a carboxylic acid group in a fixed disposition with respect to the xanthenone chromophore. None of the compounds showed superior potency to XAA itself, with virtually all alterations in the nature of the anionic center or its geometry with respect to the chromophore greatly reducing or abolishing activity. However, alpha-methylation of the side chain was permissible, and the two enantiomers of 5-methyl-alpha-methyl-XAA were separated and tested. Both were active, but the S-(+) enantiomer was much more dose-potent than the R-(-) enantiomer, in both the in vivo tumor necrosis assay and an in vitro assay measuring the stimulation of nitric oxide production by macrophages. This suggests that the enantiomers have different intrinsic activities, rather than differing in their vivo metabolism.

  DOI：

  10.1021/jm00113a027