6,8-二溴-4-羟基香豆素 | 288399-84-8

• 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: 6,8-二溴-4-羟基香豆素
• 英文名称: 6,8-dibromo-4-hydroxy-1-benzopyran-2-one
• 英文别名: 4-hydroxy-6,8-dibromo-2H-chromen-2-one；6,8-dibromo-4-hydroxy-2H-chromen-2-one；6,8-dibromo-4-hydroxy-coumarin；6,8-Dibrom-4-hydroxy-cumarin；6,8-dibromo-4-hydroxycoumarin；6,8-dibromo-4-hydroxychromen-2-one
• CAS: 288399-84-8
• 化学式: C₉H₄Br₂O₃
• 分子量: 319.937
• InChiKey: ZBFSIIJUFKSXPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,8-二溴-4-羟基香豆素 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 4-(3-aminopropoxy)-6,8-dibromo-1-benzopyran-2-one trifluoroacetate
  参考文献：
  名称：

  Design, synthesis and characterization of a novel class of coumarin-based inhibitors of inducible nitric oxide synthase

  摘要：

  Inducible nitric oxide synthase (iNOS) has been implicated in various central and peripheral pathophysiological diseases. Our high throughput screening initially identified a weak inhibitor of iNOS, thiocoumarin 13. From this lead, a number of potent derivatives were prepared that demonstrate favorable potency, selectivity and kinetics. Compound 30 has an IC50 of 60 nM for mouse iNOS and 185-fold and 9-fold selectivity for bovine eNOS and rat nNOS, respectively. In cellular assays for iNOS, this compound has micromolar potency. Furthermore, two compounds (16 and 30) demonstrate a reasonable pharmacokinetic profile in rodents. The synthesis, SAR, and biological activity of this novel class of compounds is described.

  DOI：

  10.1016/j.bmc.2005.02.036
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 6,8-二溴-4-羟基香豆素
  参考文献：
  名称：

  Anschuetz, Justus Liebigs Annalen der Chemie, 1909, vol. 368, p. 33

  摘要：

  DOI：

文献信息

• [EN] SUBSTITUTED FUROCHROMENE COMPOUNDS OF ANTIINFLAMMATORY ACTION<br/>[FR] COMPOSES DE FUROCHROMENE SUBSTITUES A ACTION ANTI-INFLAMMATOIRE
  申请人：PLIVA ISTRAZIVACKI INST D O O

  公开号：WO2005010006A1

  公开（公告）日：2005-02-03

  The present invention relates to novel compounds of the formula (I) including all stereoisomers and tautomers, to the pharmaceutically acceptable salts and solvates thereof, to the processes and reactive intermediates for their preparation and to their use in the prophylaxis and treatment of asthma and other inflammatory diseases and/or conditions in humans.

  本发明涉及公式（I）的新化合物，包括所有立体异构体和互变异构体，以及其药用可接受盐和溶剂合物，用于预防和治疗人类的哮喘和其他炎症性疾病和/或情况的过程和反应中间体，以及它们的使用。
• Pd-catalyzed chemo-selective mono-arylations and bis-arylations of functionalized 4-chlorocoumarins with triarylbismuths as threefold arylating reagents
  作者：Maddali L.N. Rao、Abhijeet Kumar

  DOI：10.1016/j.tet.2014.07.059

  日期：2014.9

  4-chlorocoumarins were studied under palladium catalysis using triarylbismuths as threefold arylating reagents. The high reactivity of 4-chlorocoumarins was demonstrated delivering mono- and bis-arylation products in a chemo-selective manner. The reaction conditions employed are simple, robust and the threefold coupling reactivity of triarylbismuth reagents was witnessed with good to high yields in 2–4 h conditions

  在钯催化下，使用三芳基铋作为三重芳基化试剂，研究了不同取代的4-氯香豆素的交叉偶联反应。证明了4-氯香豆素的高反应性以化学选择性方式递送单芳基化和双芳基化产物。所采用的反应条件简单，稳定，并且在2-4小时的条件下，三芳基铋试剂的三重偶联反应性得到了良好的证明。在合成一些天然存在的新黄酮（3.27 – 3.30）中探索了该方法的实用性。另外，4-芳基香豆素3.1产物是制备（R）-托特罗定的有用前体。
• Coumarins as iNOS inhibitors
  申请人：Jackson Sharon

  公开号：US20050054681A1

  公开（公告）日：2005-03-10

  The present invention relates to coumarins of the formula (I): that are useful as inhibitors of nitric oxide synthase. Pharmaceutical compositions and methods of using these compounds as inhibitors of nitric oxide synthase are described herein.

  本发明涉及一种具有以下结构的香豆素（I）：这些化合物可作为一氧化氮合酶的抑制剂。本文描述了这些化合物作为一氧化氮合酶抑制剂的药物组合物和使用方法。
• Pd-catalyzed cross-coupling study of bi-functional 3-bromo-4-trifloxycoumarins with triarylbismuth reagents
  作者：Maddali L.N. Rao、Abhijeet Kumar

  DOI：10.1016/j.tet.2015.05.060

  日期：2015.8

  3-bromo-4-trifloxycoumarins have been explored with threefold arylating triarylbismuth reagents. These palladium-catalyzed reactions afforded chemo-selective C-4 arylations with the facile formation of 3-bromo-4-arylcoumarins in good to high yields. Additionally, palladium-catalyzed arylations of functionalized 3-bromo-4-arylcoumarins also participated in the second arylation to give functionalized 3,4-diarylcoumarins

  已经用三重芳基化三芳基铋试剂研究了功能化的3-溴-4-三氟香豆素的交叉偶联反应。这些钯催化的反应提供了化学选择性的C-4芳基化，并以高收率或高收率容易地形成了3-bromo-4-芳基香豆素。另外，官能化的3-溴-4-芳基香豆素的钯催化的芳基化也参与第二芳基化，以高收率得到官能化的3,4-二芳基香豆素。
• Synthesis and Biological Evaluation of Coumarin-Based Inhibitors of NAD(P)H: Quinone Oxidoreductase-1 (NQO1)
  作者：Karen A. Nolan、Jeremy R. Doncaster、Mark S. Dunstan、Katherine A. Scott、A. David Frenkel、David Siegel、David Ross、John Barnes、Colin Levy、David Leys、Roger C. Whitehead、Ian J. Stratford、Richard A. Bryce

  DOI：10.1021/jm9011609

  日期：2009.11.26

  inhibit NQO1 and computed binding affinity. We have solved the crystal structure of NQO1 complexed to a hybrid compound and find good agreement with the in silico model. For both MIA PaCa-2 pancreatic tumor cells and HCT116 colon cancer cells, dicoumarol shows the greatest toxicity of all compounds. Thus, we provide a computational, synthetic, and biological platform to generate competitive NQO1 inhibitors

  这里报道了人类 NAD(P)H 醌氧化还原酶-1 (NQO1) 的两种新型抑制剂的合成，NQO1 是一种在几种类型的肿瘤细胞中过度表达的酶。第一个系列包含取代的对称双香豆素类似物；第二个系列包含杂化化合物，其中一个 4-羟基香豆素系统被不同的芳族部分取代。在存在和不存在添加蛋白质的情况下，几种化合物显示出与双香豆素相当或改善的 NQO1 抑制作用。此外，还证明了这些药物抑制 NQO1 的能力与计算的结合亲和力之间的相关性。我们已经解决了 NQO1 与杂化化合物络合的晶体结构，并发现与计算机模拟模型。对于 MIA PaCa-2 胰腺肿瘤细胞和 HCT116 结肠癌细胞，双香豆素显示出所有化合物中最大的毒性。因此，我们提供了一个计算、合成和生物平台，以生成具有优于双香豆素的药理特性的竞争性 NQO1 抑制剂。这将允许对细胞中的 NQO1 活性进行更明确的研究，特别是其药物激活/解毒特性和调节癌蛋白稳定性的能力。