3-Bromo-7-methoxy-8-(3-methylbutyl)chromen-2-one | 1261244-22-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-Bromo-7-methoxy-8-(3-methylbutyl)chromen-2-one
• CAS: 1261244-22-7
• 化学式: C₁₅H₁₇BrO₃
• 分子量: 325.202
• InChiKey: MBXKJRGYIGUBJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Bromo-7-methoxy-8-(3-methylbutyl)chromen-2-one 、 4-三氟甲氧基苯硼酸 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以40.8%的产率得到7-methoxy-8-(3-methylbutyl)-3-(4-trifluoromethoxyphenyl)chromen-2-one
  参考文献：
  名称：

  Discovery of novel osthole derivatives as potential anti-breast cancer treatment

  摘要：

  Osthole, an ingredient of Traditional Chinese Medicine (TCM) from natural product Cnidium monnieri (L.) Cusson, was used as a lead compound for structural modification. A series of osthole derivatives bearing aryl substituents at 3-position of coumarin, has been prepared and evaluated for their growth inhibitory activity against human breast cancer cell lines MCF-7 and MDA-MB-231. Interestingly, some derivatives exhibited good inhibition, among them compound 8e was found to be the most potent compound with IC50 values of 0.24 mu M, 0.31 mu M against MCF-7 and MDA-MB-231, respectively, which was improved more than 100-folds compared with its parent compound osthole. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.027
• 作为产物：
  描述：

  8-异戊基-7-甲氧基-2H-色烯-2-酮 在 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以25%的产率得到3-Bromo-7-methoxy-8-(3-methylbutyl)chromen-2-one
  参考文献：
  名称：

  Discovery of novel osthole derivatives as potential anti-breast cancer treatment

  摘要：

  Osthole, an ingredient of Traditional Chinese Medicine (TCM) from natural product Cnidium monnieri (L.) Cusson, was used as a lead compound for structural modification. A series of osthole derivatives bearing aryl substituents at 3-position of coumarin, has been prepared and evaluated for their growth inhibitory activity against human breast cancer cell lines MCF-7 and MDA-MB-231. Interestingly, some derivatives exhibited good inhibition, among them compound 8e was found to be the most potent compound with IC50 values of 0.24 mu M, 0.31 mu M against MCF-7 and MDA-MB-231, respectively, which was improved more than 100-folds compared with its parent compound osthole. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.027