4-(3-bromopropoxy)-2,3,6-trimethylphenol | 213276-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(3-bromopropoxy)-2,3,6-trimethylphenol
• CAS: 213276-21-2
• 化学式: C₁₂H₁₇BrO₂
• 分子量: 273.17
• InChiKey: HIFQAUHKZPSXPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3-bromopropoxy)-2,3,6-trimethylphenol 在 sodium hydroxide 、 四溴化碳 、 sodium hydride 、 三苯基膦 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.17h， 生成 1-[2-[3-(1-hydroxy-2,3,6-trimethylphenoxy)propyloxy]ethyl]-2-(4-methyl-1-homopiperazino)-1H-benzimidazole
  参考文献：
  名称：

  Synthesis and biological activities of novel antiallergic agents with 5-lipoxygenase inhibiting action

  摘要：

  Novel benzimidazole derivatives were synthesized and their pharmacological activities were examined. These compounds showed a good suppressive action on histamine release from rat peritoneal mast cells produced by antigen-antibody reaction, an antagonistic action on guinea pig ileum contraction caused by histamine, an inhibitory action on 5-lipoxygenase in rat basophilic leukemia-1 (RBL-1) cells, and a preventive action on NADPH dependent lipid peroxidation induced by Fe3+-ADP in rat liver microsomes. In addition, 1-[2-[2-(4-Hydroxy-2,3,5-trimethylphenoxy)ethoxyl-ethyl]-2-(4-methyl-1-homopiperazino)-1H-benzimidazole difumarate (BOM1006) exhibited a dose dependent suppressive action on 48 h homologous passive cutaneous anaphylaxis (PCA) reaction in rats orally administered the drug. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00291-6
• 作为产物：
  描述：

  三甲基氢醌 、 3-溴-1-丙醇 在 phosphomolybdic acid 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以40%的产率得到4-(3-bromopropoxy)-2,3,6-trimethylphenol
  参考文献：
  名称：

  合成具有抗氧化作用的抗过敏剂三甲基氢醌衍生物。

  摘要：

  合成了一系列新的三甲基对苯二酚衍生物，并评价了它们在大鼠肝微粒体中的抗脂质过氧化活性，抑制大鼠嗜碱性白血病1（RBL-1）细胞5-脂氧合酶和48h同源被动皮肤过敏（PCA）活性。大鼠。4- [4- [4-（二苯甲基）-1-哌嗪基]-丁氧基] -2,3,6-三甲基苯酚（9c）具有抑制Fe（3 +）-ADP诱导的NADPH依赖性脂质过氧化的能力（IC50 ＝ 5.3×10（-7）M），5-脂氧合酶（（IC 50 ＝ 3.5×10（-7）M）和PCA反应（100mg / kg po时抑制57％）。

  DOI：

  10.1248/cpb.47.177

文献信息

• Synthesis of Benzimidazole Derivatives as Antiallergic Agents with 5-Lipoxygenase Inhibiting Action.
  作者：Hiroyuki NAKANO、Tsutomu INOUE、Nobuhide KAWASAKI、Hideki MIYATAKA、Hitoshi MATSUMOTO、Takeo TAGUCHI、Naoki INAGAKI、Hiroichi NAGAI、Toshio SATOH

  DOI：10.1248/cpb.47.1573

  日期：——

  Syntheses were conducted of novel benzimidazole derivatives that suppress histamine release from mast cells, inhibit 5-lipoxygenase, and possess antioxidative action. Among the compounds synthesized, 1-[2-[2-(4-hydroxy- 2,3,5-trimethylphenoxy)ethoxy]ethyl]-2-(4-methyl-1- homopiperazino)benzimidazole (22) potently suppressed histamine release from rat peritoneal mast cells triggered by the antigen-antibody

  合成了新的苯并咪唑衍生物，这些衍生物可抑制组胺从肥大细胞中释放，抑制5-脂氧合酶并具有抗氧化作用。在合成的化合物中，1- [2- [2-（4-羟基-2,3,5-三甲基苯氧基）乙氧基]乙基] -2-（4-甲基-1-高哌嗪基）苯并咪唑（22）有效抑制组胺的释放抗原抗体反应触发大鼠腹膜肥大细胞中的表达，抑制大鼠嗜碱性白血病1（RBL-1）细胞中的5-脂氧合酶，并阻止Fe（3 +）-ADP诱导大鼠肝中NADPH依赖性脂质过氧化微粒体，除了拮抗组胺引起的豚鼠回肠的收缩。
• Synthesis of Trimethylhydroquinone Derivatives as Anti-allergic Agents with Anti-oxidative Actions.
  作者：Nobuhide KAWASAKI、Hideki MIYATAKA、Mayumi NISHIKI、Hitoshi MATSUMOTO、Naoki INAGAKI、Hiroichi NAGAI、Toshio SATOH

  DOI：10.1248/cpb.47.177

  日期：——

  A novel series of trimethylhydroquinone derivatives was synthesized and evaluated for their anti-lipid peroxidation activity in rat liver microsomes, inhibition of rat basophilic leukemia-1 (RBL-1) cell 5-lipoxygenase and 48 h homologous passive cutaneous anaphylaxis (PCA) activity in rats. 4-[4-[4-(Diphenylmethyl)-1-piperazinyl]-butoxy]-2,3,6-trimethyl phenol (9c) exhibited the ability to inhibit

  合成了一系列新的三甲基对苯二酚衍生物，并评价了它们在大鼠肝微粒体中的抗脂质过氧化活性，抑制大鼠嗜碱性白血病1（RBL-1）细胞5-脂氧合酶和48h同源被动皮肤过敏（PCA）活性。大鼠。4- [4- [4-（二苯甲基）-1-哌嗪基]-丁氧基] -2,3,6-三甲基苯酚（9c）具有抑制Fe（3 +）-ADP诱导的NADPH依赖性脂质过氧化的能力（IC50 ＝ 5.3×10（-7）M），5-脂氧合酶（（IC 50 ＝ 3.5×10（-7）M）和PCA反应（100mg / kg po时抑制57％）。
• Synthesis and biological activities of novel antiallergic agents with 5-lipoxygenase inhibiting action
  作者：Hiroyuki Nakano、Tsutomu Inoue、Nobuhide Kawasaki、Hideki Miyataka、Hitoshi Matsumoto、Takeo Taguchi、Naoki Inagaki、Hiroichi Nagai、Toshio Satoh

  DOI：10.1016/s0968-0896(99)00291-6

  日期：2000.2

  Novel benzimidazole derivatives were synthesized and their pharmacological activities were examined. These compounds showed a good suppressive action on histamine release from rat peritoneal mast cells produced by antigen-antibody reaction, an antagonistic action on guinea pig ileum contraction caused by histamine, an inhibitory action on 5-lipoxygenase in rat basophilic leukemia-1 (RBL-1) cells, and a preventive action on NADPH dependent lipid peroxidation induced by Fe3+-ADP in rat liver microsomes. In addition, 1-[2-[2-(4-Hydroxy-2,3,5-trimethylphenoxy)ethoxyl-ethyl]-2-(4-methyl-1-homopiperazino)-1H-benzimidazole difumarate (BOM1006) exhibited a dose dependent suppressive action on 48 h homologous passive cutaneous anaphylaxis (PCA) reaction in rats orally administered the drug. (C) 2000 Elsevier Science Ltd. All rights reserved.