4-phenethylaminocoumarin | 111222-28-7

• 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: 4-phenethylaminocoumarin
• 英文别名: 2H-1-Benzopyran-2-one, 4-[(2-phenylethyl)amino]-；4-(2-phenylethylamino)chromen-2-one
• CAS: 111222-28-7
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: BWZATJSVMMHRIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  169-171 °C
• 沸点：
  471.0±44.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)
• 溶解度：
  1.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-phenethylaminocoumarin 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 生成 2-Oxo-4-[(2-phenylethyl)amino]-2H-1-benzopyran-3-carboxaldehyde
  参考文献：
  名称：

  A Novel Transformation of 4-Arylaminocoumarins to 6H-1-Benzopyrano[4,3-b]quinolin-6-ones Under V ilsmeier-Haack Conditions

  摘要：

  通过 4-羟基香豆素与适当的胺反应，制备出 4-芳基和 4-烷基氨基香豆素 1。在 Vilsmeier-Haack 条件下，4-烷基氨基香豆素可生成 3-甲酰基衍生物 3。

  DOI：

  10.1055/s-1987-27930
• 作为产物：
  描述：

  4-羟基香豆素 、 2-苯乙胺 以70%的产率得到4-phenethylaminocoumarin
  参考文献：
  名称：

  Synthesis and Photophysical Properties of 1,4-Dihydro-2H,5H-chromeno[4,3-d][1,3]oxazin-5-ones, and Derivatives Containing Tethered 1,2,3-Triazoles, from 4-Aminocoumarins

  摘要：

  一种简便的方法用于将4-氨基香豆素经H2SO4介导的羟甲基化/环化N,O-缩醛化反应转化为1,4-二氢-2H,5H-色诺[4,3-d][1,3]噁唑啉-5-酮，产率中等至良好，已经开发并优化。还研究了该转化的范围和限制，该反应发生在水或水/THF混合物中。所得三环化合物的氮原子用于连接烷基、芳基和1,2,3-三唑基甲基基团，对后者采用两步点击化学方法。还研究了杂环化合物以及它们的1,2,3-三唑衍生物的光物理性质。N-芳基衍生物表现出高量子产率的荧光（高达Φf = 0.69）和非常大的斯托克斯位移（高达201 nm）。

  DOI：

  10.1055/s-0037-1612428

文献信息

• Chavan, Abhijit P., Journal of Chemical Research, 2006, # 3, p. 179 - 181
  作者：Chavan, Abhijit P.

  DOI：——

  日期：——
• Synthesis, structure, and estrogenic activity of 4-amino-3-(2-methylbenzyl)coumarins on human breast carcinoma cells
  作者：Yves Jacquot、Ioanna Laïos、Anny Cleeren、Denis Nonclercq、Laurent Bermont、Bernard Refouvelet、Kamal Boubekeur、Alain Xicluna、Guy Leclercq、Guy Laurent

  DOI：10.1016/j.bmc.2007.01.025

  日期：2007.3

  A number of coumarins exhibit interesting pharmacological activities and are therefore of therapeutic use. We report here the synthesis and the structural analysis of new N-substituted 4-amino-3-(2-methylbenzyl)coumarins (compounds 8a-8e) that present structural analogies with estrothiazine and 11- or 7-substituted 17 beta-estradiol. These derivatives were tested with respect to estrogenic activity on the estrogen receptor positive (ER+) human MCF-7 breast cancer cell line. Two of the reported compounds (8a and 8b) stimulated specifically the proliferation of MCF-7 cells, but not that of estrogen receptor negative (ER-) human MDA-MB-231 breast cancer cells, suggesting that their mitogenic activity is mediated by ER. Accordingly, the stimulating effect of 8a and 8b was suppressed by the pure antiestrogen fulvestrant. Besides, 8a and 8b induced ER down-regulation similar to that produced by classical ER agonists or pure antagonists. The effects of the compounds under study on ER-mediated transcription were assessed on (ER+) MVLN cells, that is, MCF-7 cells stably transfected with a pVit-tk-Luc reporter plasmid. Derivatives 8a and 8b, and surprisingly compound 8c, enhanced ER-mediated gene transactivation in that model. Finally, no coumarin was able to compete with tritiated 17 beta-estradiol ([H-3]E-2) for ER binding, suggesting unconventional interactions with the receptor, such as interactions with the second binding pocket or with the coactivator-binding region. To conclude, observations performed in this study on compound 8c reveal that estrogenic activity can be dissociated from enhancement of cell proliferation. Furthermore, ERE-driven transactivation of transcription seems to be a condition necessary, but not sufficient, for estrogen-induced stimulation of cell growth. (c) 2007 Elsevier Ltd. All rights reserved.
• TABAKOVIC K.; TABAKOVIC I.; AJDINI N.; LECI O., SYNTHESIS,(1987) N 3, 308-310
  作者：TABAKOVIC K.、 TABAKOVIC I.、 AJDINI N.、 LECI O.

  DOI：——

  日期：——
• Synthesis and Photophysical Properties of 1,4-Dihydro-2H,5H-chromeno[4,3-d][1,3]oxazin-5-ones, and Derivatives Containing Tethered 1,2,3-Triazoles, from 4-Aminocoumarins
  作者：Marina C. Dilelio、Nathan P. Brites、Larissa A. Vieira、Bernardo A. Iglesias、Teodoro S. Kaufman、Claudio C. Silveira

  DOI：10.1055/s-0037-1612428

  日期：2019.8

  A facile protocol for the unprecedented one-pot H2SO4-mediated hydroxymethylation/cyclative N,O-acetalization of 4-aminocoumarins to 1,4-dihydro-2H,5H-chromeno[4,3-d][1,3]oxazin-5-ones, in moderate to good yields, was developed and optimized. The scope and limitations of the transformation, which takes place in water or water/THF mixtures, were also studied. The nitrogen atom of the resulting tricycles was used to tether alkyl, aryl and 1,2,3-triazolylmethyl moieties, employing a two-step click chemistry approach for the latter. The photophysical properties of the heterocycles, as well as of their 1,2,3-triazole derivatives, were also examined. The N-aryl derivatives exhibited high quantum yields of fluorescence (up to Φf = 0.69) and very large Stokes shifts (up to 201 nm).

  一种简便的方法用于将4-氨基香豆素经H2SO4介导的羟甲基化/环化N,O-缩醛化反应转化为1,4-二氢-2H,5H-色诺[4,3-d][1,3]噁唑啉-5-酮，产率中等至良好，已经开发并优化。还研究了该转化的范围和限制，该反应发生在水或水/THF混合物中。所得三环化合物的氮原子用于连接烷基、芳基和1,2,3-三唑基甲基基团，对后者采用两步点击化学方法。还研究了杂环化合物以及它们的1,2,3-三唑衍生物的光物理性质。N-芳基衍生物表现出高量子产率的荧光（高达Φf = 0.69）和非常大的斯托克斯位移（高达201 nm）。
• A Novel Transformation of 4-Arylaminocoumarins to 6<i>H</i>-1-Benzopyrano[4,3-b]quinolin-6-ones Under V ilsmeier-Haack Conditions
  作者：K. Tabaković、I. Tabaković、N. Ajdini、O. Leci

  DOI：10.1055/s-1987-27930

  日期：——

  4-Aryl and 4-alkylaminocoumarins 1 were prepared by reacting of 4-hydroxycoumarin and an appropriate amine. The reaction of 1 with phosphorusoxychloride/dimethylformamide led to 6 H-1-benzopyrano[4,3-b]quinoline-6-one derivatives 2 in very good yields, while 4-alkylaminocoumarins gave 3-formyl derivatives 3 under Vilsmeier-Haack conditions.

  通过 4-羟基香豆素与适当的胺反应，制备出 4-芳基和 4-烷基氨基香豆素 1。在 Vilsmeier-Haack 条件下，4-烷基氨基香豆素可生成 3-甲酰基衍生物 3。