4'-dimethylaminoisoflavone | 1119201-63-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4'-dimethylaminoisoflavone
• 英文别名: 3-[4-(Dimethylamino)phenyl]chromen-4-one；3-[4-(dimethylamino)phenyl]chromen-4-one
• CAS: 1119201-63-6
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: HHIRMOGLOHEZQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-dimethylaminoisoflavone 、 胍 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-[2-Amino-5-[4-(dimethylamino)phenyl]pyrimidin-4-yl]phenol
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2,4,5-substituted pyrimidine derivatives for anticancer activity

  摘要：

  A series of novel 2,4,5-substituted pyrimidine derivatives were synthesized and evaluated for inhibition against the human hepatocellular carcinoma BEL-7402 cancer cell line. Several compounds showed potent inhibition with an IC50 value less than 0.10 mu M. Structure-activity relationships for this class of compounds at the 2- and 5-position of the pyrimidine scaffold have been elucidated. The most active compound 7gc showed good inhibition of several different human cancer cell lines with IC50 values from 0.024 to 0.55 mu M. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.067
• 作为产物：
  描述：

  色酮 、 4-溴-N,N-二甲基苯胺 在 zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex 、 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 48.5h， 以83%的产率得到4'-dimethylaminoisoflavone
  参考文献：
  名称：

  路易斯酸触发的 Chromones、Quinolones 和 Thiochromones 的选择性锌化：在天然黄酮和异黄酮制备中的应用

  摘要：

  路易斯酸引发的锌化允许各种色酮和喹诺酮的区域选择性金属化。在没有 MgCl(2) 的情况下，观察到 C(3) 锌化，而在 MgCl(2) 或相关的路易斯酸存在的情况下，会发生 C(2) 锌化。显示了对天然黄酮、异黄酮和喹诺酮的应用。

  DOI：

  10.1021/ja306178q

文献信息

• Lewis Acid-Triggered Selective Zincation of Chromones, Quinolones, and Thiochromones: Application to the Preparation of Natural Flavones and Isoflavones
  作者：Lydia Klier、Tomke Bresser、Tobias A. Nigst、Konstantin Karaghiosoff、Paul Knochel

  DOI：10.1021/ja306178q

  日期：2012.8.22

  A Lewis acid-triggered zincation allows the regioselective metalation of various chromones and quinolones. In the absence of MgCl(2), a C(3) zincation is observed, whereas in the presence of MgCl(2) or a related Lewis acid, C(2) zincation occurs. Applications to a natural flavone, isoflavone, and quinolone are shown.

  路易斯酸引发的锌化允许各种色酮和喹诺酮的区域选择性金属化。在没有 MgCl(2) 的情况下，观察到 C(3) 锌化，而在 MgCl(2) 或相关的路易斯酸存在的情况下，会发生 C(2) 锌化。显示了对天然黄酮、异黄酮和喹诺酮的应用。
• Synthesis and biological evaluation of novel 2,4,5-substituted pyrimidine derivatives for anticancer activity
  作者：Fuchun Xie、Hongbing Zhao、Lizhi Zhao、Liguang Lou、Youhong Hu

  DOI：10.1016/j.bmcl.2008.09.067

  日期：2009.1

  A series of novel 2,4,5-substituted pyrimidine derivatives were synthesized and evaluated for inhibition against the human hepatocellular carcinoma BEL-7402 cancer cell line. Several compounds showed potent inhibition with an IC50 value less than 0.10 mu M. Structure-activity relationships for this class of compounds at the 2- and 5-position of the pyrimidine scaffold have been elucidated. The most active compound 7gc showed good inhibition of several different human cancer cell lines with IC50 values from 0.024 to 0.55 mu M. (C) 2008 Elsevier Ltd. All rights reserved.