1-(4-bromophenoxy)-4-chloro-2-methoxybenzene | 1428626-86-1

• 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: 1-(4-bromophenoxy)-4-chloro-2-methoxybenzene
• CAS: 1428626-86-1
• 化学式: C₁₃H₁₀BrClO₂
• 分子量: 313.578
• InChiKey: NJDHNWFQFCLFEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenoxy)-4-chloro-2-methoxybenzene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium tert-butylate 、 三溴化硼 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 生成 5-Chloro-2-[4-(4-methylpiperazin-1-yl)phenoxy]phenol
  参考文献：
  名称：

  Design, synthesis, and biological activity of diaryl ether inhibitors of Toxoplasma gondii enoyl reductase

  摘要：

  Triclosan is a potent inhibitor of Toxoplasma gondii enoyl reductase (TgENR), which is an essential enzyme for parasite survival. In view of triclosan's poor druggability, which limits its therapeutic use, a new set of B-ring modified analogs were designed to optimize its physico-chemical properties. These derivatives were synthesized and evaluated by in vitro assay and TgENR enzyme assay. Some analogs display improved solubility, permeability and a comparable MIC50 value to that of triclosan. Modeling of these inhibitors revealed the same overall binding mode with the enzyme as triclosan, but the B-ring modifications have additional interactions with the strongly conserved Asn130. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.019
• 作为产物：
  描述：

  4-氯-2-甲氧基苯酚 、 4-溴苯硼酸 在 氧气 、 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以70%的产率得到1-(4-bromophenoxy)-4-chloro-2-methoxybenzene
  参考文献：
  名称：

  Design, synthesis, and biological activity of diaryl ether inhibitors of Toxoplasma gondii enoyl reductase

  摘要：

  Triclosan is a potent inhibitor of Toxoplasma gondii enoyl reductase (TgENR), which is an essential enzyme for parasite survival. In view of triclosan's poor druggability, which limits its therapeutic use, a new set of B-ring modified analogs were designed to optimize its physico-chemical properties. These derivatives were synthesized and evaluated by in vitro assay and TgENR enzyme assay. Some analogs display improved solubility, permeability and a comparable MIC50 value to that of triclosan. Modeling of these inhibitors revealed the same overall binding mode with the enzyme as triclosan, but the B-ring modifications have additional interactions with the strongly conserved Asn130. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.019