(E)-4-bromopentoxystilbene | 131530-04-6

• 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-bromopentoxystilbene
• 英文别名: (E)-4-(5-bromopentyloxy)stilbene；1-(5-bromopentoxy)-4-[(E)-2-phenylethenyl]benzene
• CAS: 131530-04-6
• 化学式: C₁₉H₂₁BrO
• 分子量: 345.279
• InChiKey: CTXVVFUIBWEOTL-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-4-bromopentoxystilbene 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以100%的产率得到(E)-4-(5-iodopentyloxy)stilbene
  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：

  1,5-二溴戊烷 、 反式-4-羟基芪 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以48%的产率得到(E)-4-bromopentoxystilbene
  参考文献：
  名称：

  Wyrzykiewicz, Elzbieta; Wybieralska, Jadwiga; Grzesiak, Jolanta, Polish Journal of Chemistry, 1990, vol. 64, # 1-6, p. 323 - 331

  摘要：

  DOI：

文献信息

• 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.
• WYRZYKIEWICZ, ELZBIETA;WYBIERALSKA, JADWIGA;GRZESIAK, JOLANTA;PRUKALA, WI+, POL. J. CHEM., 64,(1990) N-6, C. 323-331
  作者：WYRZYKIEWICZ, ELZBIETA、WYBIERALSKA, JADWIGA、GRZESIAK, JOLANTA、PRUKALA, WI+

  DOI：——

  日期：——