4-hydroxy-3-(1-(p-tolylamino)ethyl)-2H-chromen-2-one | 1220118-17-1

• 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: 4-hydroxy-3-(1-(p-tolylamino)ethyl)-2H-chromen-2-one
• 英文别名: 4-Hydroxy-3-(1-(p-tolylamino)ethyl)-2h-chromen-2-one；4-hydroxy-3-[1-(4-methylanilino)ethyl]chromen-2-one
• CAS: 1220118-17-1
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: HDHMNJJGKXBDEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-hydroxy-3-(1-(p-tolylimino)ethyl)-2H-chromen-2-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以86%的产率得到4-hydroxy-3-(1-(p-tolylamino)ethyl)-2H-chromen-2-one
  参考文献：
  名称：

  An efficient synthesis and antioxidant properties of novel imino and amino derivatives of 4-hydroxy coumarins

  摘要：

  通过传统和微波促进程序合成了一系列 4-羟基香豆素的亚氨基和氨基衍生物，并通过不同的体外模型（如 DPPH 自由基清除活性、亚油酸乳液模型系统、还原力测定和磷钼法等）对其抗氧化潜力进行了评估。所有制备的化合物都具有良好的抗氧化活性，其中对硝基苯基衍生物 6c 的 IC50 值为 25.9 μM，具有与标准 BHT 相当的自由基清除活性，而苄基氨基化合物 8c 的还原力最佳（RP50 值为 255.6 μM）。观察到的数据还表明，这些化合物可以作为脂质过氧化过程的抑制剂。

  DOI：

  10.1007/s12272-010-2220-z

文献信息

• Substituted imino and amino derivatives of 4-hydroxycoumarins as novel antioxidant, antibacterial and antifungal agents: Synthesis and in vitro assessments
  作者：Nenad Vukovic、Slobodan Sukdolak、Slavica Solujic、Neda Niciforovic

  DOI：10.1016/j.foodchem.2009.11.040

  日期：2010.6

  A series of imino and amino derivatives of 4-hydroxycoumarins were synthesised and evaluated for antioxidant potential, through different in vitro models such as (DPPH) free radical-scavenging activity, linoleic acid emulsion model system, reducing power assay and phosphomolybdenum method. Also, anti microbial activity of obtained coumarins was evaluated against 13 bacteria and eight fungi. All prepared Compounds possessed good antioxidant activity and among them a p-nitrophenol derivative with IC50 at 25.9 mu M possessed radical-scavenging activity which was comparable to BHT. Observed data for antibacterial activity indicated strong activity of all tested amino derivatives, while imines showed better antifungal properties. (C) 2009 Elsevier Ltd. All rights reserved.
• An efficient synthesis and antioxidant properties of novel imino and amino derivatives of 4-hydroxy coumarins
  作者：Nenad Vukovic、Slobodan Sukdolak、Slavica Solujic、Neda Niciforovic

  DOI：10.1007/s12272-010-2220-z

  日期：2010.1

  Series of imino and amino derivatives of 4-hydroxy coumarins were synthesized via conventional and microwave promoted procedure and evaluated for antioxidant potential through different in vitro models such as (DPPH) free radical scavenging activity, linoleic acid emulsion model system, reducing power assay and phosphomolybdenum method. All prepared compounds possess good antioxidant activity and among them p-nitro-phenyl derivative 6c with IC50 at 25.9 μM possesses radical scavenging activity which is comparable to standard BHT, while the best reducing power was observed in a case of benzyl amino compound 8c (RP50 255.6 μM). Also, observed data indicated that compounds may serve as inhibitors of lipid peroxidation process.

  通过传统和微波促进程序合成了一系列 4-羟基香豆素的亚氨基和氨基衍生物，并通过不同的体外模型（如 DPPH 自由基清除活性、亚油酸乳液模型系统、还原力测定和磷钼法等）对其抗氧化潜力进行了评估。所有制备的化合物都具有良好的抗氧化活性，其中对硝基苯基衍生物 6c 的 IC50 值为 25.9 μM，具有与标准 BHT 相当的自由基清除活性，而苄基氨基化合物 8c 的还原力最佳（RP50 值为 255.6 μM）。观察到的数据还表明，这些化合物可以作为脂质过氧化过程的抑制剂。