(E)-4-bromopropoxystilbene | 710954-63-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-4-bromopropoxystilbene
• 英文别名: (E)-1-(3-bromopropoxy)-4-styrylbenzene；(E)-4-(3-bromopropyloxy)stilbene；1-(3-bromopropoxy)-4-[(E)-2-phenylethenyl]benzene
• CAS: 710954-63-5
• 化学式: C₁₇H₁₇BrO
• 分子量: 317.225
• InChiKey: SDEIYXQIRCKWLY-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-4-bromopropoxystilbene 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 (E)-4-(3-triphenylphosphoniumpropyloxy)stilbene iodide
  参考文献：
  名称：

  Potent Antiglioblastoma Agents by Hybridizing the Onium-Alkyloxy-Stilbene Based Structures of an α7-nAChR, α9-nAChR Antagonist and of a Pro-Oxidant Mitocan

  摘要：

  Adenocarcinoma and glioblastoma cell lines express alpha 7- and alpha 9 alpha 10-containing nicotinic acetylcholine receptors (nAChRs), whose activation promotes tumor cell growth. On these cells, the triethylammoniumethyl ether of 4-stilbenol MG624, a known selective antagonist of alpha 7 and alpha 9 alpha 10 nAChRs, has antiproliferative activity. The structural analogy of MG624 with the mitocan RDM-4'BTPI, triphenylphosphoniumbutyl ether of pterostilbene, suggested us that molecular hybridization among their three substructures (stilbenoxy residue, alkylene linker, and terminal onium) and elongation of the alkylene linker might result in novel antitumor agents with higher potency and selectivity. We found that lengthening the ethylene bridge in the triethylammonium derivatives results in more potent and selective toxicity toward adenocarcinoma and glioblastoma cells, which was paralleled by increased alpha 7 and alpha 9 alpha 10 nAChR antagonism and improved ability of reducing mitochondrial ATP production. Elongation of the alkylene linker was advantageous also for the triphenylphosphonium derivatives resulting in a generalized enhancement of antitumor activity, associated with increased mitotoxicity.

  DOI：

  10.1021/acs.jmedchem.8b01052
• 作为产物：
  描述：

  对羟基苯甲醛 在 sodium hydride 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-4-bromopropoxystilbene
  参考文献：
  名称：

  一类含巯基芳香化合物制备方法及其在抗 HIV病毒方面的应用

  摘要：

  本发明公开了一类含巯基芳香化合物的制备方法及其在抗HIV病毒方面的应用。所述化合物具有式I所示结构，本发明所述式I的化合物以宿主自身保守细胞蛋白PCAF BRD为作用靶点，具有潜在解决HIV病毒高度变异所带来的抗药性问题，有较好的抑制HIV病毒增殖的活性，且对人正常淋巴细胞的毒性较低，能够应用于抑制HIV病毒增殖的药物的制备中。

  公开号：

  CN106496084B

文献信息

• Synthesis and physicochemical characterization of fluorescent (<i>E</i>)-2-stilbenyloxyalkylthiouracils and isomer differentiation using EIMS
  作者：Elzbieta Wyrzykiewicz、Monika Wendzonka

  DOI：10.1002/jhet.5570410207

  日期：2004.3

  Twelve new fluorescent (E)-2-stilbenyloxyalkylthiouracils and 6-methyluracils 5a-51 were prepared. EI induced mass spectral fragmentation of these compounds was investigated. Fragmentation pathways are proposed on the basis of accurate mass and metastable transition measurements. Correlation between the intensities of the M+ and the selected fragment ions of these compounds is discussed. The data obtained

  制备了十二个新的荧光（E）-2-苯乙烯基氧基烷基硫尿嘧啶和6-甲基尿嘧啶5a-51。EI诱导了这些化合物的质谱裂解。在精确的质量和亚稳态跃迁测量的基础上提出了断裂途径。讨论了M +强度与这些化合物的选定碎片离子之间的相关性。所获得的数据允许区分同质异构体。这些化合物的1 H和13 C NMR光谱使用异核（HETCOR）光谱和化学位移的组合明确分配。从这些光谱得到的数据可用于区分异构体。
• Synthesis and antimicrobial activity of new (E)-4-[piperidino (4'-methylpiperidino-, morpholino-) N-alkoxy]stilbenes
  作者：Elżbieta Wyrzykiewicz、Monika Wendzonka、Bogdan Kędzia

  DOI：10.1016/j.ejmech.2005.11.010

  日期：2006.4

  The synthesis of twenty-one new (E)-4-[piperidino-(4'-methylpiperidino-, morpholino-)N-alkoxy] stilbenes is reported. The compounds were tested for antimicrobial activities against Gram-negative, Gram-positive bacteria, and fungi. In particular, compounds 3b, 3c, 3f, 3g, 3h, 3k, 3I showed good antibacterial activity against Staphylococcus aureus and 3h, 3k, 3m, 3n also against Bacillus subtilis, as well as 3h, 3n also against Streptococcus faecalis. (c) 2006 Elsevier SAS. All rights reserved.
• Potent Antiglioblastoma Agents by Hybridizing the Onium-Alkyloxy-Stilbene Based Structures of an α7-nAChR, α9-nAChR Antagonist and of a Pro-Oxidant Mitocan
  作者：Francesco Bavo、Susanna Pucci、Francesca Fasoli、Carmen Lammi、Milena Moretti、Vanessa Mucchietto、Donatella Lattuada、Paola Viani、Clara De Palma、Roberta Budriesi、Irene Corradini、Cheryl Dowell、J. Michael McIntosh、Francesco Clementi、Cristiano Bolchi、Cecilia Gotti、Marco Pallavicini

  DOI：10.1021/acs.jmedchem.8b01052

  日期：2018.12.13

  Adenocarcinoma and glioblastoma cell lines express alpha 7- and alpha 9 alpha 10-containing nicotinic acetylcholine receptors (nAChRs), whose activation promotes tumor cell growth. On these cells, the triethylammoniumethyl ether of 4-stilbenol MG624, a known selective antagonist of alpha 7 and alpha 9 alpha 10 nAChRs, has antiproliferative activity. The structural analogy of MG624 with the mitocan RDM-4'BTPI, triphenylphosphoniumbutyl ether of pterostilbene, suggested us that molecular hybridization among their three substructures (stilbenoxy residue, alkylene linker, and terminal onium) and elongation of the alkylene linker might result in novel antitumor agents with higher potency and selectivity. We found that lengthening the ethylene bridge in the triethylammonium derivatives results in more potent and selective toxicity toward adenocarcinoma and glioblastoma cells, which was paralleled by increased alpha 7 and alpha 9 alpha 10 nAChR antagonism and improved ability of reducing mitochondrial ATP production. Elongation of the alkylene linker was advantageous also for the triphenylphosphonium derivatives resulting in a generalized enhancement of antitumor activity, associated with increased mitotoxicity.
• 一类含巯基芳香化合物制备方法及其在抗 HIV病毒方面的应用
  申请人：中国科学技术大学

  公开号：CN106496084B

  公开（公告）日：2019-05-17

  本发明公开了一类含巯基芳香化合物的制备方法及其在抗HIV病毒方面的应用。所述化合物具有式I所示结构，本发明所述式I的化合物以宿主自身保守细胞蛋白PCAF BRD为作用靶点，具有潜在解决HIV病毒高度变异所带来的抗药性问题，有较好的抑制HIV病毒增殖的活性，且对人正常淋巴细胞的毒性较低，能够应用于抑制HIV病毒增殖的药物的制备中。