6-(p-tolyl)-2H-chromen-2-one | 1259294-15-9

• 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: 6-(p-tolyl)-2H-chromen-2-one
• 英文别名: 6-(4-Methylphenyl)chromen-2-one
• CAS: 1259294-15-9
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: RDVLNTDGXZRZLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-溴水杨醛 在 四(三苯基膦)钯 、 水 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 6-(p-tolyl)-2H-chromen-2-one
  参考文献：
  名称：

  （6-和7-苯基）香豆素衍生物的合成及生物评价作为17β-羟基甾体脱氢酶1型的选择性非甾体抑制剂

  摘要：

  17β-羟基类固醇脱氢酶1（17β-HSD1）是一种酶，可催化NADPH依赖性的弱雌激素雌酮还原为最有效的雌激素雌二醇，后者通过雌激素受体发挥增殖作用。17β-HSD1在雌激素反应性组织中的过表达与激素依赖性疾病的发展有关，例如乳腺癌和子宫内膜异位症。因此，17β-HSD1代表了开发新疗法的诱人靶标。我们发现，在重组酶分析中，简单的香豆素1和2可以显着抑制17β-HSD1，对17β-HSD2具有高选择性。我们假设引入了各种p-使用Suzuki-Miyaura交叉偶联反应将香豆素核心的6或7位取代的苯基部分提供类固醇结构的模拟物，对17β-HSD1的抑制作用得到改善。该系列中最好的抑制剂被证明是6a，IC 50为270 nM，对17β-HSD1的选择性比对17β-HSD2的要好，并且对α和β雌激素受体的选择性也很高。

  DOI：

  10.1021/jm101104z

文献信息

• Mechanism insight and scope of PEPPSI-catalyzed cross-coupling reaction between triarylbismuth and arylbromide
  作者：Bénédicte Cassirame、Sylvie Condon、Christophe Pichon

  DOI：10.1016/j.molcata.2016.07.016

  日期：2016.12

  In this paper we report the first cross-coupling reaction of Ar3Bi with Ar'X mediated by Pd-NHC complexes by keeping the ability of Ar3Bi to transfer the three aryl moieties. Investigations were carried out in order to minimize the quantity of the side product Ar-Ar coming from the conversion of Ar3Bi. The results showed that PEPPSI IPr was a good catalyst precursor. Efforts were focussed on the rule of each additive such as PPh3 and the base. It was notably found that the presence of PPh3 (ratio PEPPSI IPriPPh(3): 1/1) was essential to keep the process efficient. Therefore NHC-Pd-PPh3 has been assumed as being the catalytic species. Under the optimized reaction conditions the concomitant formation of the undesired biaryl side product was restricted to its inherent formation consecutive to the reduction of the catalyst precursor to Pd(0). In a last study, the scope and the limitation of the new catalytic methodology were examined and a large range of unsymmetrical biaryl compounds Ar-Ar' bearing various substituents from strongly electron-donating to electron-withdrawing ones have been prepared and fully characterized. (C) 2016 Elsevier B.V. All rights reserved.
• Synthesis and Biological Evaluation of (6- and 7-Phenyl) Coumarin Derivatives as Selective Nonsteroidal Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 1
  作者：Štefan Starčević、Petra Brožič、Samo Turk、Jožko Cesar、Tea Lanišnik Rižner、Stanislav Gobec

  DOI：10.1021/jm101104z

  日期：2011.1.13

  coumarines 1 and 2 significantly inhibit 17β-HSD1 in a recombinant enzyme assay, with high selectivity against 17β-HSD2. We postulated that the introduction of various p-substituted phenyl moieties to position 6 or 7 of the coumarin core using the Suzuki-Miyaura cross-coupling reaction would provide mimetics of steroidal structures with improved inhibition of 17β-HSD1. The best inhibitor in the series

  17β-羟基类固醇脱氢酶1（17β-HSD1）是一种酶，可催化NADPH依赖性的弱雌激素雌酮还原为最有效的雌激素雌二醇，后者通过雌激素受体发挥增殖作用。17β-HSD1在雌激素反应性组织中的过表达与激素依赖性疾病的发展有关，例如乳腺癌和子宫内膜异位症。因此，17β-HSD1代表了开发新疗法的诱人靶标。我们发现，在重组酶分析中，简单的香豆素1和2可以显着抑制17β-HSD1，对17β-HSD2具有高选择性。我们假设引入了各种p-使用Suzuki-Miyaura交叉偶联反应将香豆素核心的6或7位取代的苯基部分提供类固醇结构的模拟物，对17β-HSD1的抑制作用得到改善。该系列中最好的抑制剂被证明是6a，IC 50为270 nM，对17β-HSD1的选择性比对17β-HSD2的要好，并且对α和β雌激素受体的选择性也很高。