7-phenyl-2H-chromen-2-one | 115560-43-5

• 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: 7-phenyl-2H-chromen-2-one
• 英文别名: 7,8-Phenylcoumarin；7-phenylchromen-2-one
• CAS: 115560-43-5
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: POUGEZZPCFDFHD-UHFFFAOYSA-N

物化性质

• 沸点：
  410.8±34.0 °C(predicted)
• 密度：
  1.218±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-phenyl-2H-chromen-2-one 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 methyl (E)-3-[4-phenyl-2-(trifluoromethylsulfonyloxy)phenyl]prop-2-enoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation ofortho-ArylN-Hydroxycinnamides as Potent Histone Deacetylase (HDAC) 8 Isoform-Selective Inhibitors

  摘要：

  AbstractHistone deacetylases (HDACs) are a family of enzymes that play a crucial role in biological process and diseases. In contrast to other isozymes, HDAC8 is uniquely incapable of histone acetylation. In order to delineate its physiological function, we developed HDAC8‐selective inhibitors using knowledge‐based design combined with structural modeling techniques. Enzyme inhibitory analysis demonstrated that some of the resulting compounds (22 b, 22 d, 22 f, and 22 g) exhibited anti‐HDAC8 activity superior to PCI34051, a known HDAC8‐specific inhibitor, with IC50 values in the range of 5–50 nM. Among them, compound 22 d showed antiproliferative effects toward several human lung cancer cell lines (A549, H1299, and CL1‐5); it exhibited cytotoxicity against human lung CL1‐5 cells similar to that of SAHA yet without significant cytotoxicity for normal IMR‐90 cells. Expression profiling of HDAC isoforms in three cancer cell lines indicated that the HDAC8 level in CL1‐5 is higher than that in H1299 and CL1‐1 cells, a result consistent with the differential cytotoxicity of compound 22 d. These results suggest the effectiveness of our design concept, which may lead to a tool compound for studying the specific role of HDAC8 in cellular biological processes.

  DOI：

  10.1002/cmdc.201200300
• 作为产物：
  描述：

  7-甲氧基香豆素 在 吡啶 、 aluminum (III) chloride 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 7-phenyl-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

• Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst
  作者：Bin Zhao、Bo Xu

  DOI：10.1039/d0ob02417a

  日期：——

  coumarin derivatives via a tandem double bond isomerization/oxidative cyclization of cinnamic acids. Inexpensive and stable xanthone was used as the photocatalyst, and readily available Selectfluor was used as the oxidant. This method tolerates a wide range of functional groups and offers excellent chemical yields in general. Besides, the photocatalytic oxidative cyclization of cinnamic acid esters gives

  我们已经通过肉桂酸的串联双键异构化/氧化环化开发了一种香豆素衍生物的有效光催化合成方法。廉价，稳定的x吨酮用作光催化剂，易购的Selectfluor用作氧化剂。该方法可耐受各种官能团，并且通常可提供出色的化学收率。此外，肉桂酸酯的光催化氧化环化得到二聚的木脂素型产物。
• Structure−Activity Relationship and Molecular Mechanisms of Ethyl 2-Amino-4-(2-ethoxy-2-oxoethyl)-6-phenyl-4<i>H</i>-chromene-3-carboxylate (sHA 14-1) and Its Analogues
  作者：Sonia G. Das、Jignesh M. Doshi、Defeng Tian、Sadiya N. Addo、Balasubramanian Srinivasan、David L. Hermanson、Chengguo Xing

  DOI：10.1021/jm9005059

  日期：2009.10.8

  excitingly, our studies of 5q in camptothecin (CCRF-CEM/C2) and mitoxantrone (HL-60/MX2) resistant cancer cells highlight its ability to selectively kill drug-resistant cells over parent cancer cells. 5q inhibits tumor cell growth through the induction of apoptosis, with detailed mechanism of its selectivity toward drug-resistant cancer cells under investigation. These results suggest that 5q is a promising

  对当前疗法的多种耐药性的快速发展是癌症治疗中的主要障碍。因此，可以克服癌细胞中获得的耐药性的抗癌剂非常重要。以前，我们已经证明2-氨基-4-（2-乙氧基-2-氧代乙基）-6-苯基-4 H-苯甲基-3-羧酸乙酯（5a，sHA 14-1）是乙基2的稳定类似物-氨基-6-溴-4-（1-氰基-2-乙氧基-2-氧代乙基）-4 H-苯甲基-3-羧酸盐（6，HA 14-1），减轻耐药性并与多种癌症协同作用白血病细胞的疗法。5a的结构活性关系（SAR）研究指导了乙基2-氨基-6-（3'，5'-二甲氧基苯基）-4-（2-乙氧基-2-氧代乙基）-4的发展H - chromene -3-carboxylate（5q，CXL017），一种对多种血液学和实体瘤细胞具有低微摩尔细胞毒性的化合物。更令人兴奋的是，我们对喜树碱（CCRF-CEM / C2）和米托蒽醌（HL-60 / MX2）耐药癌细胞中的5q的研究突显了
• One-pot catalysis of dehydrogenation of cyclohexanones to phenols and oxidative Heck coupling: expedient synthesis of coumarins
  作者：Donghee Kim、Minsik Min、Sungwoo Hong

  DOI：10.1039/c3cc41296b

  日期：——

  One-pot reactions leading to highly functionalized coumarins have been developed via a Pd(II)-catalyzed dehydrogenation-oxidative Heck-cyclization process.

  通过Pd（II）催化的脱氢-氧化Heck环化过程已经开发出了导致高度功能化香豆素的一锅法反应。
• Bichromatic Photosynthesis of Coumarins by UV Filter-Enabled Olefin Metathesis
  作者：Or Eivgi、Revannath L. Sutar、Ofer Reany、N. Gabriel Lemcoff

  DOI：10.1002/adsc.201700316

  日期：2017.7.17

  Herein, we report on a two-step bichromatic synthesis of coumarins involving UV-A and UV-C light. The first step is a UV-A-photoinduced ruthenium-catalyzed cross-metathesis (CM) reaction of 2-nitrobenzyl-protected 2-hydroxystyrenes with acrylates, using an external solution of 1-pyrenecarboxaldehyde as a UV filter. Irradiation in the absence of the filter permanently inhibits the light-activated catalyst

  在本文中，我们报道了涉及UV-A和UV-C光的香豆素的两步双色合成。第一步是使用1- car甲醛的外部溶液作为UV过滤剂，将2-硝基苄基保护的2-羟基苯乙烯与丙烯酸酯进行UV-A光诱导的钌催化的交叉复分解（CM）反应。在不存在滤光片的情况下进行辐照会永久抑制光活化的催化剂，这是由于光不稳定的保护基团（PPG）的光裂解以及酚盐与钌的螯合所致。CM后简单地去除外部滤光片，就可以与UV-C光进行进一步的光化学反应，以实现更复杂的结构，例如本研究中提出的香豆素。
• ORGANIC LIGHT-EMITTING DEVICE INCLUDING FLUORESCENT COMPOUND AND FLUORESCENT COMPOUND
  申请人：Samsung Electronics Co., Ltd.

  公开号：US20190074445A1

  公开（公告）日：2019-03-07

  An organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer and a fluorescent compound, wherein the fluorescent compound comprises a 3 n-π*-to- 1 π-π* energy transition from a 3 n-π* excited state to a 1 π-π* excited state, an energy level in a 1 n-π* excited state of the fluorescent compound is greater than an energy level in the 1 π-π* excited state of the fluorescent compound, the fluorescent compound emits a fluorescent light by radiative energy transition of an exciton in the 1 π-π* excited state to a ground state, and the energy level in the 1 n-π* excited state, the energy level in the 1 π-π* excited state, and the energy level in the 3 n-π* excited state are each independently calculated by using a time dependent-Density Functional Theory method.

  一种有机发光器件，包括：第一电极；面向第一电极的第二电极；以及设置在第一电极和第二电极之间的有机层，其中，有机层包括一个发射层和一个荧光化合物，荧光化合物包括从a3n-π*激发态到a1π-π*激发态的a3n-π*-to-1π-π*能量跃迁，荧光化合物在a1n-π*激发态的能级高于荧光化合物在1π-π*激发态的能级，荧光化合物通过1π-π*激发态中的激子的辐射能量跃迁到基态发射荧光，且1n-π*激发态的能级、1π-π*激发态的能级和3n-π*激发态的能级分别通过使用时间依赖密度泛函理论方法独立计算。