2,6-bis<2-(tetrahydro-2H-pyran-2-yloxy)ethoxy>benzaldehyde | 170957-75-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,6-bis<2-(tetrahydro-2H-pyran-2-yloxy)ethoxy>benzaldehyde
• CAS: 170957-75-2
• 化学式: C₂₁H₃₀O₇
• 分子量: 394.465
• InChiKey: ZXDOTSVWNIASJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,6-bis<2-(tetrahydro-2H-pyran-2-yloxy)ethoxy>benzaldehyde 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以0.702 g的产率得到2,6-bis(2-hydroxyethoxy)benzaldehyde
  参考文献：
  名称：

  Synthesis of 2,6-disubstituted benzylamine derivatives as reversible selective inhibitors of copper amine oxidases

  摘要：

  In order to obtain substrate-like inhibitors of copper amine oxidases (CAOs), a class of enzymes involved in important cellular processes as well as in crosslinking of elastin and collagen and removal of biogenic primary amines, we synthesized a set of benzylamine derivatives properly substituted at positions 2 and 6 and studied their biological activity towards some members of CAOs.With benzylamines 6, 7, 8 containing linear alkoxy groups we obtained reversible inhibitors of benzylamine oxidase (BAO), very active and selective toward diamine oxidase (DAO), lysyl oxidase (LO) and monoamine oxidase B (MAO B) characterized by a certain toxicity consequent to the crossing of the brain barrier. Poorly toxic, up to very active, reversible inhibitors of BAO, very selective toward DAO, LO and MAO B, were obtained with benzylamines 10, 11, 12 containing hydrophilic x-hydroxyalkoxy groups. With benzylamines 13, 14, 15, containing linear alkyl groups endowed with steric, but not conjugative effects for the absence of properly positioned oxygen atoms, we synthesized moderately active inhibitors of BAO reversible and selective toward DAO, LO and MAO B.The cross examination of the entire biological data brought us to the conclusion that the bioactive synthesized compounds most likely exert their physiological role of reversible inhibitors in consequence of the formation of a plurality of hydrogen bonds or hydrophobic non-covalent interactions with proper sites in the protein. Accordingly, the reported inhibitors may be considered as a set of research tools for general biological studies and the formation of enzyme complexes useful for X-ray structure determinations aimed at the design of more sophisticated inhibitors to always better modulate the protein activity without important side effects. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.037
• 作为产物：
  描述：

  间苯二酚 在 正丁基锂 、 sodium hydride 作用下， 以 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 、 Petroleum ether 为溶剂， 反应 7.0h， 生成 2,6-bis<2-(tetrahydro-2H-pyran-2-yloxy)ethoxy>benzaldehyde
  参考文献：
  名称：

  Synthesis of 2,6-disubstituted benzylamine derivatives as reversible selective inhibitors of copper amine oxidases

  摘要：

  In order to obtain substrate-like inhibitors of copper amine oxidases (CAOs), a class of enzymes involved in important cellular processes as well as in crosslinking of elastin and collagen and removal of biogenic primary amines, we synthesized a set of benzylamine derivatives properly substituted at positions 2 and 6 and studied their biological activity towards some members of CAOs.With benzylamines 6, 7, 8 containing linear alkoxy groups we obtained reversible inhibitors of benzylamine oxidase (BAO), very active and selective toward diamine oxidase (DAO), lysyl oxidase (LO) and monoamine oxidase B (MAO B) characterized by a certain toxicity consequent to the crossing of the brain barrier. Poorly toxic, up to very active, reversible inhibitors of BAO, very selective toward DAO, LO and MAO B, were obtained with benzylamines 10, 11, 12 containing hydrophilic x-hydroxyalkoxy groups. With benzylamines 13, 14, 15, containing linear alkyl groups endowed with steric, but not conjugative effects for the absence of properly positioned oxygen atoms, we synthesized moderately active inhibitors of BAO reversible and selective toward DAO, LO and MAO B.The cross examination of the entire biological data brought us to the conclusion that the bioactive synthesized compounds most likely exert their physiological role of reversible inhibitors in consequence of the formation of a plurality of hydrogen bonds or hydrophobic non-covalent interactions with proper sites in the protein. Accordingly, the reported inhibitors may be considered as a set of research tools for general biological studies and the formation of enzyme complexes useful for X-ray structure determinations aimed at the design of more sophisticated inhibitors to always better modulate the protein activity without important side effects. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.037

文献信息

• New 2,3-dihydro-5h-1,4-benzodioxepin derivatives. Easy formation and x-ray structure determination of a pentacyclic acetal containing a fourteen-membered carbon-oxygen ring
  作者：Francesco Lucchesini、Vincenzo Bertini、Marco Pocci、Giovanni De Munno、Alessandra Crispini

  DOI：10.1016/0040-4020(95)00583-t

  日期：1995.8

  3-dihydro-5H-1,4-benzodioxepin derivatives are prepared and a fourteen-membered tetraoxy-genated macrocycle is obtained in 81% yield without special synthetic expedients. The solid state molecular structure of the macrocyclic compound is determined by single crystal X-ray analysis.

  在各种条件下研究了2,6-双（2-羟基乙氧基）苯甲醛（4）的酸催化缩醛化反应。制备了新的2,3-二氢-5 H -1,4-苯并二恶英衍生物，无需特殊的合成方法，就可以以81％的收率获得十四元的四氧合大环。大环化合物的固态分子结构通过单晶X射线分析确定。