5-bromo-8-hydroxypsoralen | 1930-60-5

• 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: 5-bromo-8-hydroxypsoralen
• 英文别名: 4-Brom-xanthotoxol；5-Brom-xanthotoxol；4-bromo-9-hydroxy-furo[3,2-g]chromen-7-one；5-Bromoxanthotoxol；4-bromo-9-hydroxyfuro[3,2-g]chromen-7-one
• CAS: 1930-60-5
• 化学式: C₁₁H₅BrO₄
• 分子量: 281.062
• InChiKey: ZBPLCCWLBRIGPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bromo-8-hydroxypsoralen 在 吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 di(1-adamantyl)benzylphosphonium bromide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 26.0h， 生成 9-((4-(dimethylamino)phenyl)ethynyl)-4-((4-(trifluoromethyl)phenyl)ethynyl)-7H-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  Fluorescent Donor–Acceptor Psoralen Cruciforms by Consecutive Suzuki–Suzuki and Sonogashira–Sonogashira One-Pot Syntheses

  摘要：

  Two novel donor-acceptor cruciform topologies are efficiently synthesized by site-selective Suzuki-Suzuki and Sonogashira-Sonogashira multicomponent reactions starting from a bromo-triflato-functionalized psoralen scaffold. In addition to tunability of photophysical properties, such as absorption and emission, many derivatives possess partially high relative fluorescence quantum yields in solution and fluoresce strongly in the solid state. Additionally, the promising compounds show solvatochromism and acidochromic effects. In addition, 8-p-anisyl-5-p-cyanophenyl-substituted psoralen exhibits aggregation-induced emission properties. Experimentally (applying the Lippert-Mataga model) and computationally (TD-DFT calculations), the pronounced charge transfer character of the longest wavelength absorption band was confirmed.

  DOI：

  10.1021/acs.joc.0c01059
• 作为产物：
  描述：

  欧前胡素 在 溴 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 以98%的产率得到5-bromo-8-hydroxypsoralen
  参考文献：
  名称：

  Kadry, H.; Osman, A. N.; Al-Azizi, M., Revue Roumaine de Chimie, 1992, vol. 37, # 8, p. 915 - 920

  摘要：

  DOI：

文献信息

• Psoralen sensitizers for viral inactivation
  申请人：The Ohio State Research Foundation

  公开号：US05919935A1

  公开（公告）日：1999-07-06

  The present invention relates to novel, halogenated psoralen compounds that are useful for inactivating vital contaminants in blood-derived products, particularly blood-derived products that contain platelets or red blood cells. The psoralen compounds of the present invention have the following formula: The side chain S which is a attached to the carbon at position 8 of the psoralen moiety contains a quartemary ammonium group which comprises a central nitrogen atom, a linking group L, and an aromatic ring structure. The linking group L joins the central nitrogen atom of the quartenary ammonium group to the psoralen moiety. The linking group L comprises a carbon chain having 2 to 12 carbon atoms and an oxygen atom which links the carbon chain to the psoralen moiety. The psoralen compounds of the present invention also comprise one or more halogens attached to the psoralen moiety. Preferably the halogens are attached to the carbon atom at position 3 or 5 of the psoralen moiety. In one class of these novel psoralen compounds, the central nitrogen atom of the quartenary ammonium group is a component of the aromatic ring structure. In another class, the central nitrogen atom is attached to three substituent groups, R.sup.1, R.sup.2, and R.sup.3 wherein R.sup.3 has the following structure: --R.sup.5 --CH.dbd.CH--R.sup.6 wherein R.sup.5 is a carbon chain comprising 1 to 3 carbon atoms, and wherein R.sup.6 is the aromatic ring, The present invention also relates to methods of making and using the novel psoralen compounds.

  本发明涉及一种新型的卤代花檬素化合物，该化合物对血液制品中的重要污染物具有灭活作用，特别是对含有血小板或红细胞的血液制品具有作用。本发明的花檬素化合物具有以下结构式：侧链S连接到花檬素部分的第8位碳上，其中包含一个四级铵基，该四级铵基包括一个中心氮原子、一个连接基团L和一个芳香环结构。连接基团L连接四级铵基的中心氮原子与花檬素部分。连接基团L包括一个含有2至12个碳原子的碳链和一个氧原子，将碳链连接到花檬素部分。本发明的花檬素化合物还包括一个或多个连接到花檬素部分的卤素。优选地，这些卤素连接到花檬素部分的第3位或第5位碳原子。在这些新型花檬素化合物的一类中，四级铵基的中心氮原子是芳香环结构的一部分。在另一类中，中心氮原子连接到三个取代基团R.sup.1、R.sup.2和R.sup.3，其中R.sup.3具有以下结构：--R.sup.5--CH.dbd.CH--R.sup.6，其中R.sup.5是一个含有1至3个碳原子的碳链，R.sup.6是芳香环。本发明还涉及制备和使用这种新型花檬素化合物的方法。
• Synthesis and fluorescent study of 5-phenyl furocoumarin derivatives as vasodilatory agents
  作者：Cheng Wang、Tao Wang、Limin Huang、Wen Lu、Jie Zhang、Huaizhen He

  DOI：10.1016/j.bmcl.2015.11.056

  日期：2016.1

  Two series of 5-phenyl furocoumarin derivatives were designed and prepared based on our previous research. All new compounds were characterized by 1H NMR, 13C NMR and mass spectra. Furthermore, they were screened for their vasodilatory activity on the mesenteric artery of Sprague-Dawley rats, and they all presented with moderate vasodilatory activity. Fluorescent properties of the target compounds

  根据我们先前的研究，设计和制备了两个系列的5-苯基呋喃香豆素衍生物。所有新化合物均通过1 H NMR，13 C NMR和质谱进行表征。此外，对它们在Sprague-Dawley大鼠的肠系膜动脉上的血管舒张活性进行了筛选，并且它们均具有中等的血管舒张活性。在甲醇中测试了目标化合物的荧光性质。在不同的溶剂，不同的pH值和迁移时间下研究了4a的荧光变化。所有结果表明，在进一步的结构修饰之后，这种类型的荧光化合物可以同时用作血管舒张剂和探针。
• Synthesis and biological evaluation of novel biphenyl-furocoumarin derivatives as vasodilator agents
  作者：Di Wei、Ya-Jing Hou、Yi-Tong Xie、Zhen-Ru Liu、Cheng Wang、Huai-Zhen He

  DOI：10.1080/10286020.2018.1540600

  日期：2020.2.1

  mesenteric artery, basilar artery and renal artery, respectively. The majority of compounds demonstrated potent vasodilatation, and compound 8e expressed the highest activity (EC50 = 0.56 μM) in MA. Compounds with fluorine at 2-position of 5-phenyl get better activity than others with chlorine or bromine, and the compounds containing a bulky structure had relatively low activity, such as 8c (EC50 = 22.39 μM)

  基于欧前胡素的核结构合成了一系列新型联苯呋喃香豆素衍生物，并通过IR，1H NMR，13C NMR和MS进行了鉴定，并评估了它们在离体大鼠肠系膜动脉，基底动脉和肾动脉上舒张血管的能力，分别。大多数化合物表现出有效的血管舒张作用，并且化合物8e在MA中表现出最高的活性（EC50 = 0.56μM）。在5-苯基2位具有氟的化合物比在氯或溴中具有更好的活性，并且具有大体积结构的化合物具有相对较低的活性，例如在MA中为8c（EC50 = 22.39μM）。随后，将8e，10e和8c停靠在L钙通道（PDB代码：3G43）中，以解释化合物活性的差异。
• Syntheses and evaluation of the antioxidant activity of novel methoxypsoralen derivatives
  作者：Stavros E. Bariamis、Marilena Marin、Constantinos M. Athanassopoulos、Christos Kontogiorgis、Zinovia Tsimali、Dionissios Papaioannou、Giovanni Sindona、Giovanni Romeo、Konstantinos Avgoustakis、Dimitra Hadjipavlou-Litina

  DOI：10.1016/j.ejmech.2012.11.043

  日期：2013.2

  respectively. The 8-MOP analogs 19 and 24, incorporating at position 5 of the psoralen nucleus a butyl acrylate or a tert-butyl cinnamate moiety, were the most powerful inhibitors of soybean LOX and inhibited effectively lipid peroxidation. Analog 19 was a more potent anti-inflammatory agent than the reference compound indomethacin and of comparable cytocompatibility to 8-MOP whereas analog 24 was a weaker

  合成了一系列适合于结构抗氧化/抗炎活性关系研究的5-和8-甲氧基补骨脂素（MOP）类似物，使用N-溴糖精对MOP进行选择性单溴化，并利用Heck反应或Suzuki偶联或Suzuki偶联，然后进行Wittig反应以分别安装丙烯酸酯或苯甲酸酯或肉桂酸酯类型的侧链。在补骨脂素核的5位掺入丙烯酸丁酯或肉桂酸叔丁酯部分的8-MOP类似物19和24是大豆LOX的最有效抑制剂，可有效抑制脂质过氧化。模拟19与消炎痛相比，消炎痛是一种比参考化合物消炎痛更有效的抗炎药，并且与8-MOP具有相当的细胞相容性，而与消炎痛相比，类似物24的消炎抑制剂弱，并且与8-MOP相比，其细胞毒性明显更高。根据结构特征讨论了生物学测试的结果。
• Method of inactivation of viral and bacterial blood contaminants
  申请人：Credit Managers Association of California

  公开号：US05587490A1

  公开（公告）日：1996-12-24

  A compound is provided for inactivating viral, bacterial or other contamination in cells, body fluids or fractions thereof. The compound comprises a psoralen with a single substituent that is either a quaternary phosphonium or ammonium moiety, and at least one substituent that is a halogen. The compound selectively binds to the contaminant, and upon activation by irradiation, damages the contaminant.

  提供了一种化合物，可用于使细胞、体液或其分离物中的病毒、细菌或其他污染物失活。该化合物包括一种带有单个取代基的柏赛灵，该取代基可以是季铵或铵基团，至少一个取代基是卤素。该化合物选择性地结合到污染物上，并在受到辐射激活后对其造成损害。