1-(5-bromopentyloxy)-4-methoxy-benzene | 125878-81-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(5-bromopentyloxy)-4-methoxy-benzene
• 英文别名: 1-(5-bromo-pentyloxy)-4-methoxy-benzene；O-Methyl-O'-(5-brom-pentyl)-hydrochinon；1-(5-Brom-pentyloxy)-4-methoxy-benzol；5-(4-Methoxy-phenoxy)-pentylbromid；1-(5-Bromopentoxy)-4-methoxybenzene
• CAS: 125878-81-1
• 化学式: C₁₂H₁₇BrO₂
• 分子量: 273.17
• InChiKey: VXKIFLBOJUNDGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-bromopentyloxy)-4-methoxy-benzene 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以91%的产率得到1-(5-iodopentoxy)-4-methoxybenzene
  参考文献：
  名称：

  Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein

  摘要：

  一系列糖缀合物，包含C-糖基化碳水化合物部分的染料木素衍生物，被合成了并在体外对人体细胞系HCT 116和DU 145进行了抗癌活性测试。目标化合物15-17通过用四丁基铵盐处理来自L-鼠李醛（1）的ω-溴烷基C-糖苷来合成。与先前研究的O-糖基化染料木素衍生物相比，这些新的、代谢稳定的类似物通过抑制细胞周期来抑制癌细胞系的增殖。

  DOI：

  10.3390/molecules19067072
• 作为产物：
  描述：

  1,5-二溴戊烷 、 4-甲氧基苯酚 在 potassium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 1-(5-bromopentyloxy)-4-methoxy-benzene
  参考文献：
  名称：

  新型苯氧基烷基吡啶鎓肟作为沙林和VX替代物抑制胆碱酯酶的脑穿透激活剂的功效

  摘要：

  吡啶鎓肟是强亲核试剂，许多是有机磷酸酶抑制胆碱酯酶（ChE）的有效活化剂。然而，当前的肟再活化剂在穿越血脑屏障和再活化完整生物中的脑ChE方面是无效的。我们的实验室已经开发了一系列取代的苯氧基烷基吡啶鎓肟（美国专利9,227,937 B2），目的是鉴定能有效跨越血脑屏障的活化剂。发现该系列的前35个在体外具有相似的特征沙林替代品（邻苯二甲酰亚胺基异丙基甲基膦酸酯，PIMP）或VX替代品（硝基苯基乙基甲基膦酸酯，NEMP）在牛脑制剂中抑制ChE活化剂的功效，如先前在大鼠脑制剂中观察到的。这些新型肟中的许多已经显示出能够降低用高致死剂量的沙林替代品（硝基苯基异丙基甲基膦酸酯，NIMP）或VX替代NEMP处理的大鼠大脑中ChE抑制水平的能力。肟给药后2小时的再活化水平高达35％，而目前批准的治疗药物2-PAM并未降低脑ChE抑制作用。另外，有证据显示几种更有效的新型肟可减轻癫痫样行为，但2-PA

  DOI：

  10.1016/j.cbi.2016.07.004

文献信息

• Effect on the conformation of monosubstituted pillar[5]arene: solvent, temperature, concentration and linker length
  作者：Zhen Fu、Yanqing Jin、Bingqian Xie、Hui Liu

  DOI：10.1039/d3ob01043k

  日期：——

  fluorescent probe (E)-4-[4-(dimethylamino)styryl-]-1-pyridinium were synthesized and characterized. The conformations of the monosubstituted pillar[5]arenes were investigated systematically by NMR and fluorescence spectroscopy and were found to be dependent on solvent polarity, concentration, temperature and linker length. PI1 with a short linker remained uncomplexed in DMSO, whereas it formed a polymer

  合成并表征了一系列带有荧光探针（E ）-4-[4-（二甲基氨基）苯乙烯基-]-1-吡啶鎓的单取代柱[5]芳烃（ PIn ）。通过核磁共振和荧光光谱系统地研究了单取代柱[5]芳烃的构象，并发现其构象取决于溶剂极性、浓度、温度和连接体长度。具有短连接基的PI1在 DMSO 中保持不复合，而在高浓度氯仿中形成聚合物。随着连接体长度的增加，PI2-4可以在自包含单体和分子间复合物之间达到平衡。浓度的增加导致在 DMSO 中形成聚合物，在氯仿中形成自渗透二聚体。结果提供了有关各种因素调节超分子组装体的信息。
• Baeuerle, Peter; Wuerthner, Frank; Heid, Stephan, Angewandte Chemie, 1990, vol. 102, # 4, p. 414 - 415
  作者：Baeuerle, Peter、Wuerthner, Frank、Heid, Stephan

  DOI：——

  日期：——
• Assessments for the courts: A survey of Australian psychologists
  作者：Alfred Allan、Mary‐Anne Martin、Maria M Allan

  DOI：10.1080/13218710009524981

  日期：2000.11
• Design, synthesis, and anti-HCV activity of thiourea compounds
  作者：Iou-Jiun Kang、Li-Wen Wang、Chung-Chi Lee、Yen-Chun Lee、Yu-Sheng Chao、Tsu-An Hsu、Jyh-Haur Chern

  DOI：10.1016/j.bmcl.2009.02.048

  日期：2009.4

  A series of thiourea derivatives were synthesized and their antiviral activity was evaluated in a cell-based HCV subgenomic replicon assay. SAR studies revealed that the chain length and the position of the alkyl linker largely influenced the in vitro anti-HCV activity of this class of potent antiviral agents. Among this series of compounds synthesized, the thiourea derivative with a six-carbon alkyl linker at the meta-position of the central phenyl ring (10) was identified as the most potent anti-HCV inhibitor (EC50 = 0.047 mu M) with a selectivity index of 596. (C) 2009 Elsevier Ltd. All rights reserved.
• Novel aryloxyalkylthioimidazoles as inhibitors of acyl-CoA: cholesterol-O-acyltransferase
  作者：M Bani、R Bormetti、W Ceccarelli、R Fiocchi、M Gobetti、M Lombroso、S Magnetti、V Olgiati、M Palladino、M Villa、E Vanotti

  DOI：10.1016/0223-5234(96)88207-9

  日期：1995.1

  A series of aryloxyalkylthioimidazoles have been synthesized and evaluated for their ability,to interfere with the enzyme acyl-CoA (cholesterol-O-acyltransferase) (ACAT, EC 2.3.1.26). Most of the molecules possessed a good in vitro ACAT inhibitory activity with IC50 values ranging between 0.1 and 2.0 mu M Some of them, eg, 2-5-[(4-isobutoxycarbonyl)phenoxy]-pentylthio} -4,5-diphenylimidazole 13, 2-3-[(4-isobutoxycarbonyl)phenoxy]-2-oximinopropylthio}-4,5-diphenylimidazole 21, 2-3-[(4-isobutoxycarbonyl)phenoxy]-2-hydrazonecarboxamidepropylthio) -4,5-diphenylimidazole 26, 2-[5-(2-pyridoxy)-pentylthio]-4,5-diphenylimidazole 40 and 2-5-[(3,5-diterbutyl-4-hydroxy)phenylthio]pentylthio}-4,5-diphenylimidazole 42, were more potent (range of activity 10-90 nM). They were also more potent with respect to the reference CI-976. When administered orally in hyperlipemic rats, at 10 and 50 mg/kg doses, some representative compounds, like 2-3-[(4-isobutoxycarbonyl)phenoxy]-2-hydroxypropylthio}-4,5-diphenylimidazole 1, 13 and 26, reduced VLDL/LDL-associated cholesterol levels by 30-50% and increased HDL cholesterol levels by 15-50%. In addition, liver accumulation of esterified cholesterol was counteracted (50-80% reduction) and liver ACAT ex vivo activity was decreased by 70-85%. Finally, the good efficacy displayed in an endogenous model of hypertriglyceridemia strongly supports the hypothesis of a good systemic availability, which constitutes one of the principal properties of a valuable ACAT inhibitor.