Triphenyl(3,4,5-trimethoxybenzyl)phosphorane hydrobromide | 111623-28-0

• 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: Triphenyl(3,4,5-trimethoxybenzyl)phosphorane hydrobromide
• 英文别名: triphenyl-[(3,4,5-trimethoxyphenyl)methylidene]-λ5-phosphane
• CAS: 111623-28-0
• 化学式: C₂₈H₂₇O₃P
• 分子量: 442.494
• InChiKey: HQBUKKHXEGJNFG-UHFFFAOYSA-N

物化性质

• 沸点：
  592.7±60.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Triphenyl(3,4,5-trimethoxybenzyl)phosphorane hydrobromide 在 碘 、 palladium diacetate 、 三溴化硼 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.5h， 生成 (E)-ethyl 3-(7-hydroxy-2-(3,4,5-trihydroxyphenyl)benzofuran-5-yl)acrylate
  参考文献：
  名称：

  羟基官能化的2-芳基苯并[ b ]呋喃的抗氧化活性和对α-葡萄糖苷酶的抑制

  摘要：

  本研究基于鸟苷酸A的结构合成了一系列羟基官能化的2-芳基苯并[ b ]呋喃，并对其抗氧化剂和α-葡萄糖苷酶的抑制活性进行了评估。化合物5a，5e和5n表现出对α-葡萄糖苷酶的显着抑制作用（IC 50值为1.9–3.0μM），并且它们似乎比槲皮素更有效。动力学结合研究表明，化合物5a和5n利用混合竞争机制抑制α-葡萄糖苷酶。该研究还揭示了化合物5a和5n与α-葡萄糖苷酶或α-葡萄糖苷酶-4-NPGP复合物结合。利用酿酒酵母α-葡萄糖苷酶的晶体结构，分子对接研究已预测化合物5a和5n通过疏水和氢相互作用与α-葡萄糖苷酶的活性位点结合。DPPH自由基清除试验进一步表明，大多数羟基官能化的2-芳基苯并[ b ]呋喃具有抗氧化活性。化合物5p是例外，该化合物在2-芳基苯并[ b ]呋喃的2-苯基环上只有一个羟基。我们的结果表明，羟基官能化的2-芳基苯并[ b]呋喃具有抗糖尿病和抗氧化特性。

  DOI：

  10.1016/j.ejmech.2015.02.024
• 作为产物：
  描述：

  三苯基-(3,4,5-三甲氧基-苄基)-溴化膦 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 Triphenyl(3,4,5-trimethoxybenzyl)phosphorane hydrobromide
  参考文献：
  名称：

  通过镍纳米粒子促进的新型Wittig型烯化反应合成白藜芦醇，DMU-212和类似物

  摘要：

  提出了一种新的白藜芦醇，DMU-212和类似物的合成方法，该方法使用苄醇作为磷的叶酸伙伴，在镍纳米粒子促进的一锅Wittig型烯烃化反应中。

  DOI：

  10.1016/j.tetlet.2009.04.023

文献信息

• Synthesis of (Z) isomers of benzoheterocyclic derivatives of combretastatin A-4: a comparative study of several methods
  作者：Thi Thanh Binh Nguyen、Thierry Lomberget、Ngoc Chau Tran、Roland Barret

  DOI：10.1016/j.tet.2013.01.005

  日期：2013.3

  monobromoalkene, a combination of hydrosilylation/vinylsilane hydrolysis and a palladium-catalyzed semi-hydrogenation step, using DMF/KOH as the hydrogen source. Our studies led us to prepare a series of diarylacetylene derivatives via a Sonogashira coupling reaction, and also to find out a copper-free basic cyclization leading to benzo[b]thiophenes. The final choice for the synthesis method of 1 strongly depends

  研究了几种制备（Z）三甲氧基苯乙烯衍生物1的方法。在发现Wittig反应导致不满意的结果后，考虑了三种不同的策略：使用DMF / KOH作为氢源的Suzuki偶联与立体定义的单溴烯烃，氢化硅烷化/乙烯基硅烷水解和钯催化的半氢化步骤的组合。我们的研究使我们通过Sonogashira偶联反应制备了一系列二芳基乙炔衍生物，并且发现了无铜的碱性环化反应，从而生成了苯并[ b ]噻吩。1的合成方法的最终选择 强烈依赖于目标化合物，但通常应优先选择避免使用有毒锡还原剂的半氢化反应。
• Transfer hydrogenation of olefins catalysed by nickel nanoparticles
  作者：Francisco Alonso、Paola Riente、Miguel Yus

  DOI：10.1016/j.tet.2009.10.057

  日期：2009.12

  Nickel nanoparticles have been found to effectively catalyse the hydrogen-transfer reduction of a variety of non-functionalised and functionalised olefins using 2-propanol as the hydrogen donor. The heterogeneous process has been shown to be highly chemoselective for certain substrates, with all the corresponding alkanes being obtained in high yields. A synthesis of the natural dihydrostilbene brittonin A is also reported based on the use of nickel nanoparticles. (C) 2009 Elsevier Ltd. All rights reserved.
• THE PREPARTION AND THE USE OF ETHOXY COMBRETASTATINS AND THEIR PRODRUGS
  申请人：Zhejiang Dade Pharmaceutical Group Co., Ltd.

  公开号：EP2065358B1

  公开（公告）日：2015-07-08
• Combretastatin A-4 inhibits cell growth and metastasis in bladder cancer cells and retards tumour growth in a murine orthotopic bladder tumour model
  作者：Cheng-Huang Shen、Jia-Jen Shee、Jin-Yi Wu、Yi-Wen Lin、Jiann-Der Wu、Yi-Wen Liu

  DOI：10.1111/j.1476-5381.2010.00861.x

  日期：2010.8

  BACKGROUND AND PURPOSEBladder cancer is a highly recurrent cancer after intravesical therapy, so new drugs are needed to treat this cancer. Hence, we investigated the anti‐cancer activity of combretastatin A‐4 (CA‐4), an anti‐tubulin agent, in human bladder cancer cells and in a murine orthotopic bladder tumour model.EXPERIMENTAL APPROACHCytotoxicity of CA‐4 was measured by 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide (MTT) assay, propidium iodide (PI) staining assay and clonogenic survival assay. In vivo microtubule assembly assay, cell cycle analyses, Western blot and cell migration assay were used to study the mechanism of CA‐4. The effect of intravesical CA‐4 therapy on the development of tumours was studied in the murine orthotopic bladder tumour model.KEY RESULTSCA‐4 inhibited microtubule polymerization in vivo. Cytotoxic IC50 values of CA‐4 in human bladder cancer cells were below 4 nM. Analyses of cell‐cycle distribution showed CA‐4 obviously induced G2‐M phase arrest with sub‐G1 formation. The analyses of apoptosis showed that CA‐4 induced caspase‐3 activation and decreased BubR1 and Bub3 in cancer cells. In addition to apoptosis, CA‐4 was also found to induce the formation of multinucleated cells. CA‐4 had a significantly reduced cell migration in vitro. Importantly, the in vivo study revealed that intravesical CA‐4 therapy retarded the development of murine bladder tumours.CONCLUSIONS AND IMPLICATIONSThese data demonstrate that CA‐4 kills bladder cancer cells by inducing apoptosis and mitotic catastrophe. It inhibited cell migration in vitro and tumour growth in vivo. Hence, CA‐4 intravesical therapy could provide another strategy for treating superficial bladder cancers.