4-[4-(4-Bromo-butoxy)-phenyl]-but-3-yn-1-ol | 299461-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[4-(4-Bromo-butoxy)-phenyl]-but-3-yn-1-ol
• 英文别名: 4-[4-(4-bromobutoxy)phenyl]but-3-yn-1-ol
• CAS: 299461-39-5
• 化学式: C₁₄H₁₇BrO₂
• 分子量: 297.192
• InChiKey: YTRRLCHTOOUEIB-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C(Solv: hexane (110-54-3))
• 沸点：
  426.3±40.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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-[4-(4-Bromo-butoxy)-phenyl]-but-3-yn-1-ol 在 氢氧化钾 、 羟胺 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 propan-2-yl N-[4-[4-[4-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]butoxy]phenyl]but-3-ynyl]-N-hydroxycarbamate
  参考文献：
  名称：

  5-Lipoxygenase inhibition by N-hydroxycarbamates in dual-function compounds

  摘要：

  A series of N-hydroxycarbamates containing a histaminergic H-1 receptor antagonist pharmacophore was synthesized. In vitro assays determined the compounds had both histaminergic binding and 5-lipoxygenase inhibiting activities comparable to the corresponding N-hydroxyurea analog. Animal models demonstrated antihistaminergic and the 5-lipopxygenase inhibitory activity, with the N-hydroxyurea analog having a better overall profile. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.023
• 作为产物：
  描述：

  3-丁炔-1-醇 、 1-(4-溴丁氧基)-4-碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到4-[4-(4-Bromo-butoxy)-phenyl]-but-3-yn-1-ol
  参考文献：
  名称：

  5-Lipoxygenase inhibition by N-hydroxycarbamates in dual-function compounds

  摘要：

  A series of N-hydroxycarbamates containing a histaminergic H-1 receptor antagonist pharmacophore was synthesized. In vitro assays determined the compounds had both histaminergic binding and 5-lipoxygenase inhibiting activities comparable to the corresponding N-hydroxyurea analog. Animal models demonstrated antihistaminergic and the 5-lipopxygenase inhibitory activity, with the N-hydroxyurea analog having a better overall profile. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.023

文献信息

• Cetirizine and loratadine-based antihistamines with 5-lipoxygenase inhibitory activity
  作者：Timothy A. Lewis、Michelle A. Young、Mark P. Arrington、Lynn Bayless、Xiong Cai、Philippe Collart、Joseph B. Eckman、James L. Ellis、Doina G. Ene、Lyn Libertine、Jean-Marie Nicolas、Ralph T. Scannell、Bruce F. Wels、Karen Wenberg、Donna M. Wypij

  DOI：10.1016/j.bmcl.2004.08.060

  日期：2004.11

  A series of compounds possessing both H, histamine receptor antagonist and 5-lipoxygenase (5-LO) inhibitory activities was synthesized. The H-1-binding scaffolds of cetirizine, efletirizine, and loratadine were linked to a lipophilic N-hydroxyurea, the 5-LO inhibiting moiety of zileuton. Both activities were observed in vivo, as was increased CYP3A4 inhibition compared to their respective single-function drugs. Selected analogs in the series were shown to be orally active in guinea pig models. (C) 2004 Elsevier Ltd. All rights reserved.