3,5-dibenzyloxybenzyltriphenyl phosphonium bromide | 24082-43-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-dibenzyloxybenzyltriphenyl phosphonium bromide
• 英文别名: (3,5-bis-benzyloxybenzyl)triphenylphosphonium bromide；[3,5-Bis(phenylmethoxy)phenyl]methyl-triphenylphosphanium;bromide；[3,5-bis(phenylmethoxy)phenyl]methyl-triphenylphosphanium;bromide
• CAS: 24082-43-7
• 化学式: Br*C₃₉H₃₄O₂P
• 分子量: 645.576
• InChiKey: HEQCJFRYTGROIM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-dibenzyloxybenzyltriphenyl phosphonium bromide 在 正丁基锂 、 三氯化铝 、 N,N-二甲基苯胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 丹叶大黄素
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Resveratrol and Analogues as Apoptosis-Inducing Agents

  摘要：

  Resveratrol 1 (3,4',5-trihydroxy-trans-stilbene), a phytoalexin present in grapes and other food products, has recently been suggested as a potential cancer chemopreventive agent based on its striking inhibitory effects on cellular events associated with cancer initiation, promotion, and progression. This triphenolic stilbene has also displayed in vitro growth inhibition in a number of human cancer cell lines. In this context, a series of cis- and trans-stilbene-based resveratrols were prepared with the aim of discovering new lead compounds with clinical potential. All the synthesized compounds were tested in vitro for cell growth inhibition and the ability to induce apoptosis in HL60 promyelocytic leukemia cells. The tested trans-stilbene derivatives were less potent than their corresponding cis isomers, except for trans-resveratrol, whose cis isomer was less active. The best results were obtained with compounds 11b and 7b, the cis-3,5-dimethoxy derivatives of rhapontigenin 10a (3,5,3'-trihydroxy-4'methoxy-trans-stilbene) and its 3'-amino derivative 10b, respectively, which showed apoptotic activity at nanomolar concentrations. The corresponding trans isomers 12b and 8b were less active both as antiproliferative and as apoptosis-inducing agents. Of interest, 11b and 7b were active toward resistant HL60R cells and their activity was higher than that of several classic chemotherapeutic agents. The flow cytometry assay showed that at 50 nM compounds 7b or 11b were able to recruit almost all cells in the apoptotic sub-G(0)-G(1) peek, thus suggesting that the main mechanism of cytotoxicity of these compounds could be the activation of apoptosis. These data indicate unambiguously that structural alteration of the stilbene motif of resveratrol can be extremely effective in producing potent apoptosis-inducing agents.

  DOI：

  10.1021/jm030785u
• 作为产物：
  描述：

  3,5-二苄氧基苯甲醇 在 三溴化磷 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 2.0h， 生成 3,5-dibenzyloxybenzyltriphenyl phosphonium bromide
  参考文献：
  名称：

  NOVEL FUNCTIONALIZED 1,3-BENZENE DIOLS AND THEIR METHOD OF USE FOR THE TREATMENT OF HEPATIC ENCEPHALOPTHY

  摘要：

  本发明的药物组合物包括在治疗肝性脑病及相关疾病中具有疾病修饰作用的新型功能化1,3-苯二酚。本发明的药物组合物还包括新型的神经保护剂。

  公开号：

  US20160311769A1

文献信息

• A Scalable Biomimetic Synthesis of Resveratrol Dimers and Systematic Evaluation of their Antioxidant Activities
  作者：Bryan S. Matsuura、Mitchell H. Keylor、Bo Li、YuXuan Lin、Shelby Allison、Derek A. Pratt、Corey R. J. Stephenson

  DOI：10.1002/anie.201409773

  日期：2015.3.16

  An efficient synthetic route to the resveratrol oligomers quadrangularin A and pallidol is reported. It features a scalable biomimetic oxidative dimerization that proceeds in excellent yield and with complete regioselectivity. A systematic evaluation of the natural products and their synthetic precursors as radical‐trapping antioxidants has revealed that, contrary to popular belief, this mode of action

  据报道，合成白藜芦醇寡聚体quadrangularin A和pallidol的有效途径。它具有可扩展的仿生氧化二聚作用，能以优异的收率和完全的区域选择性进行。对天然产物及其合成前体作为捕获自由基的抗氧化剂的系统评价表明，与普遍的看法相反，这种作用方式不太可能解释其观察到的生物活性。
• Efficient Total Synthesis of Piceatannol via (<i>E</i>)-Selective Wittig–Horner Reaction
  作者：Su Young Han、Hyun Suck Lee、Da Hye Choi、Jung Woon Hwang、Deok Mo Yang、Jong-Gab Jun

  DOI：10.1080/00397910802528944

  日期：2009.3.25

  total synthesis of piceatannol via (E)-selective Wittig–Horner reaction is demonstrated with six steps in overall 40% yield from a commercially available, cheap starting material, 3,5-dihydroxybenzoic acid. Wittig–Horner reaction of diethyl phosphonate with aldehyde showed a superior (E)-selectivity compare to Wittig reaction using triphenylphosphine. We optimized the Wittig–Horner reaction condition

  摘要 通过 (E) 选择性 Wittig-Horner 反应有效且实用地全合成 piceatannol 以六步总收率为 40% 的总产率来自市售的廉价起始材料 3,5-二羟基苯甲酸。与使用三苯基膦的 Wittig 反应相比，膦酸二乙酯与醛的 Wittig-Horner 反应显示出更好的 (E) 选择性。我们通过在四氢呋喃 (THF) 中使用 NaH (6 当量) 回流 1 小时优化了 Wittig-Horner 反应条件，得到 99% 的单一 (E)-二苯乙烯。
• Spasmolytic Effects, Mode of Action, and Structure−Activity Relationships of Stilbenoids from <i>Nidema boothii</i>^,
  作者：Yanet Hernández-Romero、Juana-Isela Rojas、Rafael Castillo、Alejandra Rojas、Rachel Mata

  DOI：10.1021/np030303h

  日期：2004.2.1

  inhibited spontaneous contractions (IC(50) = 6.26 +/- 2.5 microg/mL) of the guinea-pig ileum. Bioassay-guided fractionation of the active extract led to the isolation of the novel spiro compound 1, which was given the trivial name nidemone, and the new dihydrophenanthrene 3, characterized as 1,5,7-trimethoxy-9,10-dihydrophenanthrene-2,6-diol. In addition, the known stilbenoids aloifol II (2), 1,5,7-tri

  CH（2）Cl（2）-MeOH（1：1）提取物从Nidema Bootii的整个植物中制备，可抑制豚鼠回肠的自发收缩（IC（50）= 6.26 +/- 2.5 microg / mL）。活性提取物的生物测定指导分馏导致分离出新的螺化合物1（其名称为nidemone）和新的二氢菲3（特征为1,5,7-三甲氧基-9,10-二氢菲-2） ，6-二醇。另外，已知的西til类化合物alloifol II（2），1,5,7-三甲氧基菲-2,6-二醇（4），表蒽醌（5），没食子酚（6），表麻酚B（7），2,4-二甲氧基菲获得了-3，7-二醇（8），六硫吡啶（9）和巴他他辛III（10）。分离物通过光谱数据解释进行结构表征。化合物2-6、9 10诱导豚鼠回肠的自发收缩明显的浓度依赖性抑制作用，其IC（50）值介于0.14和2.36 microM之间。合成联苄类似物23-35，并进行药理学测试。结果表明，为
• Leveraging the Persistent Radical Effect in the Synthesis of <i>trans</i>‐2,3‐Diaryl Dihydrobenzofurans**
  作者：Bec J. Roldan、Travis A. Hammerstad、Matthew S. Galliher、Mitchell H. Keylor、Derek A. Pratt、Corey R. J. Stephenson

  DOI：10.1002/anie.202305801

  日期：2023.8.21

  A simple, diastereoselective protocol for accessing trans-2,3-diaryl dihydrobenzofurans through efficient cross-coupling of persistent quinone radicals, derived from quinone methide dimers, and transient phenoxyl radicals is described. DFT calculations have provided insight into the reaction pathway. This transformation offers access to a wide variety of dihydrobenzofuran-containing natural products

  描述了一种简单的非对映选择性方案，用于通过源自醌甲基化物二聚体的持久醌自由基和瞬时苯氧基自由基的有效交叉偶联来获得反式-2,3-二芳基二氢苯并呋喃。 DFT 计算提供了对反应途径的深入了解。这种转化提供了获得多种含二氢苯并呋喃的天然产物的机会。
• Method for treating hepatic encephalopathy or a disease associated with free radical mediate stress and oxidative stress with novel functionalized 1,3-benzene diols
  申请人：KANNALIFE SCIENCES, INC.

  公开号：US10004722B2

  公开（公告）日：2018-06-26

  Pharmaceutical compositions of the invention include novel functionalized 1,3-benzenediols having a disease-modifying action in the treatment of hepatic encephalopathy and related conditions. Pharmaceutical compositions of the invention further include novel neuroprotective agents.

  本发明的药物组合物包括新型官能化 1,3-苯二酚，在治疗肝性脑病及相关疾病方面具有疾病调节作用。本发明的药物组合物还包括新型神经保护剂。