7-O-苄基木犀草素 | 1201808-24-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 7-O-苄基木犀草素
• 英文名称: 7-benzyloxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-chromen-4-one
• 英文别名: 7-O-Benzyl Luteolin；2-(3,4-dihydroxyphenyl)-5-hydroxy-7-phenylmethoxychromen-4-one
• CAS: 1201808-24-3
• 化学式: C₂₂H₁₆O₆
• 分子量: 376.365
• InChiKey: NGOIESQGCUSOSC-UHFFFAOYSA-N

物化性质

• 熔点：
  >255°C (dec.)
• 沸点：
  670.6±55.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿和甲醇混合物（轻微加热）

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-O-苄基木犀草素 、 1-溴代异戊烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 7-benzyloxy-2-(3-hydroxy-4-(isopentyloxy)phenyl)-5-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Discovery and synthesis of novel luteolin derivatives as DAT agonists

  摘要：

  Luteolin, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one, has been proposed and proved to be a novel dopamine transporter (DAT) activator. In order to develop this potential of luteolin, a series of novel luteolin derivatives were designed, synthesized, and evaluated for their DAT agonistic activities, utilizing constructed Chinese hamster ovary (CHO) cell lines stably expressing rat DAT. Biological screening results demonstrated that luteolin derivatives 1d, 1e, and 4c carry great DAT agonistic potency (EC(50) = 0.046, 0.869, and 1.375 mu M, respectively) compared with luteolin 8 (EC(50) = 1.45 +/- 0.29 mu M). Luteolin derivative 1d, notably, exhibited a 32-fold-higher DAT agonistic potency than luteolin. These luteolin derivatives represent a novel DAT agonist class, from which lead compounds useful for exploration of additional novel DAT agonists could be drawn. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.049
• 作为产物：
  描述：

  5,7-bis(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-4H-chromen-4-one 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 9.0h， 以96.8%的产率得到7-O-苄基木犀草素
  参考文献：
  名称：

  Discovery and synthesis of novel luteolin derivatives as DAT agonists

  摘要：

  Luteolin, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one, has been proposed and proved to be a novel dopamine transporter (DAT) activator. In order to develop this potential of luteolin, a series of novel luteolin derivatives were designed, synthesized, and evaluated for their DAT agonistic activities, utilizing constructed Chinese hamster ovary (CHO) cell lines stably expressing rat DAT. Biological screening results demonstrated that luteolin derivatives 1d, 1e, and 4c carry great DAT agonistic potency (EC(50) = 0.046, 0.869, and 1.375 mu M, respectively) compared with luteolin 8 (EC(50) = 1.45 +/- 0.29 mu M). Luteolin derivative 1d, notably, exhibited a 32-fold-higher DAT agonistic potency than luteolin. These luteolin derivatives represent a novel DAT agonist class, from which lead compounds useful for exploration of additional novel DAT agonists could be drawn. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.049

文献信息

• Discovery and synthesis of novel luteolin derivatives as DAT agonists
  作者：Jiange Zhang、Xianbo Liu、Xinsheng Lei、Lei Wang、Lihe Guo、Gang Zhao、Guoqiang Lin

  DOI：10.1016/j.bmc.2010.09.049

  日期：2010.11.15

  Luteolin, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one, has been proposed and proved to be a novel dopamine transporter (DAT) activator. In order to develop this potential of luteolin, a series of novel luteolin derivatives were designed, synthesized, and evaluated for their DAT agonistic activities, utilizing constructed Chinese hamster ovary (CHO) cell lines stably expressing rat DAT. Biological screening results demonstrated that luteolin derivatives 1d, 1e, and 4c carry great DAT agonistic potency (EC(50) = 0.046, 0.869, and 1.375 mu M, respectively) compared with luteolin 8 (EC(50) = 1.45 +/- 0.29 mu M). Luteolin derivative 1d, notably, exhibited a 32-fold-higher DAT agonistic potency than luteolin. These luteolin derivatives represent a novel DAT agonist class, from which lead compounds useful for exploration of additional novel DAT agonists could be drawn. (C) 2010 Elsevier Ltd. All rights reserved.