(-)-(R)-3-(3,4-difluorophenoxy)propane-1,2-diol | 1449846-89-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (-)-(R)-3-(3,4-difluorophenoxy)propane-1,2-diol
• 英文别名: (2R)-3-(3,4-difluorophenoxy)propane-1,2-diol
• CAS: 1449846-89-2
• 化学式: C₉H₁₀F₂O₃
• 分子量: 204.173
• InChiKey: IZTASVWZHCMZJN-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(R)-3-(3,4-difluorophenoxy)propane-1,2-diol 在 吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 48.5h， 生成 (-)-Lubeluzole
  参考文献：
  名称：

  A convenient synthesis of lubeluzole and its enantiomer: Evaluation as chemosensitizing agents on human ovarian adenocarcinoma and lung carcinoma cells

  摘要：

  Lubeluzole, a neuroprotective anti-ischemic drug, and its enantiomer were prepared following a convenient procedure based on hydrolytic kinetic resolution. The ee values were >99% and 96%, respectively, as assessed by HPLC analysis. The chemosensitizing effects of both enantiomers were evaluated in combination with either doxorubicin (human ovarian adenocarcinoma A2780 cells) or paclitaxel (human lung carcinoma A549 cells) by the MTT assay. At the lowest concentrations used, lubeluzole showed an overall and remarkable tendency to synergize with both anticancer drugs. In ovarian cancer cells a clear prevalence of antagonistic effect was observed for the R-enantiomer. The synergistic effects of lubeluzole for both drugs were observed over a wide concentration window (0.005-5 mu M), the lowest limit being at least 40 times lower than human plasma concentrations previously reported as causing serious side effects. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.077
• 作为产物：
  描述：

  1-(3,4-二氟苯氧基)-2,3-环氧丙烷 在 (S,S)-(salen)cobalt(III)(OAc) 、 水 作用下， 反应 42.0h， 以30%的产率得到(+)-(S)-2-[(3,4-difluorophenoxy)methyl]oxirane
  参考文献：
  名称：

  A convenient synthesis of lubeluzole and its enantiomer: Evaluation as chemosensitizing agents on human ovarian adenocarcinoma and lung carcinoma cells

  摘要：

  Lubeluzole, a neuroprotective anti-ischemic drug, and its enantiomer were prepared following a convenient procedure based on hydrolytic kinetic resolution. The ee values were >99% and 96%, respectively, as assessed by HPLC analysis. The chemosensitizing effects of both enantiomers were evaluated in combination with either doxorubicin (human ovarian adenocarcinoma A2780 cells) or paclitaxel (human lung carcinoma A549 cells) by the MTT assay. At the lowest concentrations used, lubeluzole showed an overall and remarkable tendency to synergize with both anticancer drugs. In ovarian cancer cells a clear prevalence of antagonistic effect was observed for the R-enantiomer. The synergistic effects of lubeluzole for both drugs were observed over a wide concentration window (0.005-5 mu M), the lowest limit being at least 40 times lower than human plasma concentrations previously reported as causing serious side effects. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.077

文献信息

• A convenient synthesis of lubeluzole and its enantiomer: Evaluation as chemosensitizing agents on human ovarian adenocarcinoma and lung carcinoma cells
  作者：Maria Maddalena Cavalluzzi、Maurizio Viale、Claudio Bruno、Alessia Carocci、Alessia Catalano、Antonio Carrieri、Carlo Franchini、Giovanni Lentini

  DOI：10.1016/j.bmcl.2013.06.077

  日期：2013.9

  Lubeluzole, a neuroprotective anti-ischemic drug, and its enantiomer were prepared following a convenient procedure based on hydrolytic kinetic resolution. The ee values were >99% and 96%, respectively, as assessed by HPLC analysis. The chemosensitizing effects of both enantiomers were evaluated in combination with either doxorubicin (human ovarian adenocarcinoma A2780 cells) or paclitaxel (human lung carcinoma A549 cells) by the MTT assay. At the lowest concentrations used, lubeluzole showed an overall and remarkable tendency to synergize with both anticancer drugs. In ovarian cancer cells a clear prevalence of antagonistic effect was observed for the R-enantiomer. The synergistic effects of lubeluzole for both drugs were observed over a wide concentration window (0.005-5 mu M), the lowest limit being at least 40 times lower than human plasma concentrations previously reported as causing serious side effects. (C) 2013 Elsevier Ltd. All rights reserved.