4-溴-7-甲基-2H-色烯-2-酮 | 861537-63-5

• 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
• 中文名称: 4-溴-7-甲基-2H-色烯-2-酮
• 英文名称: 4-bromo-7-methyl-2H-chromen-2-one
• 英文别名: 4-bromo-7-methylcoumarin；4-Brom-7-methyl-cumarin；4-Bromo-7-methylchromen-2-one
• CAS: 861537-63-5
• 化学式: C₁₀H₇BrO₂
• 分子量: 239.068
• InChiKey: GOUZJAYYUNRSAW-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126 °C
• 沸点：
  346.1±42.0 °C(Predicted)
• 密度：
  1.640±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  4-溴-7-甲基-2H-色烯-2-酮 在 乙醇 、 锌 作用下， 生成 7-甲基香豆素
  参考文献：
  名称：

  Anschuetz, Justus Liebigs Annalen der Chemie, 1909, vol. 367, p. 241

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基-7-甲基香豆素 在 四磷十氧化物 、 四丁基溴化铵 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 4-溴-7-甲基-2H-色烯-2-酮
  参考文献：
  名称：

  茚满的螺二戊二烯色酮：Pd催化的螺环化，然后通过CH活化策略进行环化。

  摘要：

  已经说明了钯催化炔烃与4-溴香豆素的螺环化。该反应突出了一个有趣的过程，该过程是通过螺环化然后通过C–H活化环化来级联形成两个五元环。该方法为以高收率合成各种茚满的螺并戊二烯发色酮提供了一个有吸引力的平台。

  DOI：

  10.1021/acs.joc.0c01475

文献信息

• Synthesis and biological activities of novel ethers of quinolinone linked with coumarins
  作者：Rajesh G. Kalkhambkar、G. Aridoss、Geeta M. Kulkarni、R. M. Bapset、T. Y. Mudaraddi、N. Premkumar、Yeon Tae Jeong

  DOI：10.1007/s00706-011-0460-3

  日期：2011.3

  ethers of quinolinone linked with different substituted coumarins and benzofurans were synthesized from 4-(bromomethyl)quinolinones. All newly synthesized compounds were screened for their in vitro antibacterial and antifungal activities. Most of the compounds with chloro substitution at the C-6 or C-7 position in quinolinone showed potent antibacterial and antifungal activities. In pharmacological evaluations

  摘要由4-（溴甲基）喹啉酮合成了一系列与不同取代的香豆素和苯并呋喃连接的喹啉酮新醚。筛选所有新合成的化合物的体外抗菌和抗真菌活性。喹啉酮中大多数在C-6或C-7位置被氯取代的化合物显示出有效的抗菌和抗真菌活性。在药理学评估中，这些氯喹啉酮中的一些在8小时后也显示出70-77％的炎症抑制作用，而其他化合物显示出51-55％的抑制作用。与标准品和对照品相比，大多数化合物显示出有效的镇痛活性。通过元素分析，IR，1 H NMR，13 C NMR和EI-MS对所有新合成化合物的结构进行了表征。 图形概要
• Palladium-Catalyzed Synthesis of 4-Arylcoumarins Using Triarylbismuth Compounds as Atom-Efficient Multicoupling Organometallic Nucleophiles
  作者：Maddali L. N. Rao、Varadhachari Venkatesh、Deepak N. Jadhav

  DOI：10.1002/ejoc.201000134

  日期：——

  Triarylbismuth compounds have been cross-coupled as atom-efficient multicoupling organometallic nucleophiles with 4-bromo- and 4-(trifluoromethylsulfonyloxy)coumarins under palladium catalysis conditions. These reactions afforded an array of 4-arylcoumarins in high yields. The general palladium protocol has been demonstrated to be efficient for the coupling of both bromide and triflate derivatives

  在钯催化条件下，三芳基铋化合物作为原子高效多偶联有机金属亲核试剂与 4-溴和 4-（三氟甲基磺酰氧基）香豆素交叉偶联。这些反应以高产率提供了一系列 4-芳基香豆素。通用钯方案已被证明对于香豆素的溴化物和三氟甲磺酸酯衍生物与三芳基铋试剂的偶联是有效的。
• Novel coumarin- and quinolinone-based polycycles as cell division cycle 25-A and -C phosphatases inhibitors induce proliferation arrest and apoptosis in cancer cells
  作者：Clemens Zwergel、Brigitte Czepukojc、Emilie Evain-Bana、Zhanjie Xu、Giulia Stazi、Mattia Mori、Alexandros Patsilinakos、Antonello Mai、Bruno Botta、Rino Ragno、Denise Bagrel、Gilbert Kirsch、Peter Meiser、Claus Jacob、Mathias Montenarh、Sergio Valente

  DOI：10.1016/j.ejmech.2017.04.012

  日期：2017.7

  Cell division cycle phosphatases CDC25 A, B and C are involved in modulating cell cycle processes and are found overexpressed in a large panel of cancer typology. Here, we describe the development of two novel quinone-polycycle series of CDC25A and C inhibitors on the one hand la-k, coumarin-based, and on the other 2a-g, quinolinone-based, which inhibit either enzymes up to a sub-micro molar level and at single digit micro molar concentrations, respectively. When tested in six different cancer cell lines, compound 2c displayed the highest efficacy to arrest cell viability, showing in almost all cell lines sub-micro molar IC50 values, a profile even better than the reference compound NCS95397. To investigate the putative binding mode of the inhibitors and to develop quantitative structure-activity relationships, molecular docking and 3-D QSAR studies were also carried out. Four selected inhibitors, la, ld, 2a and 2c have been also tested in A431 cancer cells; among them, compound 2c was the most potent one leading to cell proliferation arrest and decreased CDC25C protein levels together with its splicing variant. Compound 2c displayed increased phosphorylation levels of histone H3, induction of PARP and caspase 3 cleavage, highlighting its contribution to cell death through pro-apoptotic effects. (C) 2017 Elsevier Masson SAS. All rights reserved.