2,6-bis(2-hydroxyethoxy)benzaldehyde | 170957-74-1

• 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-hydroxyethoxy)benzaldehyde
• CAS: 170957-74-1
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: QYQKUCAGBRTEAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis(2-hydroxyethoxy)benzaldehyde 在 三乙胺 作用下， 以 氘代氯仿 为溶剂， 生成 5-hydroxy-6-(2-hydroxyethoxy)-2,3-dihydro-5H-1,4-benzodioxepin
  参考文献：
  名称：

  新的2,3-二氢-5 h -1,4-苯并二恶英衍生物。含有十四元碳氧环的五环缩醛的容易形成和X射线结构测定

  摘要：

  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。

  DOI：

  10.1016/0040-4020(95)00583-t
• 作为产物：
  描述：

  1,3-bis<2-(2-tetrahydropyranyloxy)ethoxy>benzene 在 盐酸 、 正丁基锂 、 水 作用下， 以 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 7.0h， 生成 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

文献信息

• Selective inhibitors of benzylaminoxidases with respect to other
  申请人：Consiglio Nazionale Delle Ricerche

  公开号：US04888283A1

  公开（公告）日：1989-12-19

  Selective inhibitors of benzylaminoxidases, said inhibitors consisting of compounds of the general formula I ##STR1## wherein X is a group C--R.sup.4 or a nitrogen atom, R.sup.1 and R.sup.2, which can be the same or different from each other, represent hydrogen, hydroxyl groups, alkoxyl groups, or alkyl, alkenyl, hydroxyalkyl, alkoxyalkyl, hydroxyalkoxyalkyl, hydroxyalkoxyl, alkoxyalkoxyl, hydroxyalkoxyalkoxyl, phenoxyl or phenoxyalkyl groups or their substitution derivatives in the phenoxyl group, provided that no more than one of the same be hydrogen, and one or more of the symbols R.sup.3, R.sup.4 or R.sup.5 are hydrogen atoms or alkyl or hydroxyl or alkoxyl or hydroxyalkyl or hydroxyalkoxyl or hydroxyalkoxyalkyl or haloalkyl or carbonyl or carboxylic or ester or amido or nitrile or sulfonic groups or halogen atoms or nitro groups.

  苯甲醇氧化酶的选择性抑制剂，所述抑制剂由通式I的化合物组成：##STR1## 其中X是C-R4基团或氮原子，R1和R2可以相同或不同，表示氢、羟基、烷氧基或烷基、烯基、羟基烷基、烷氧基烷基、羟基烷氧基烷基、羟基烷氧基、烷氧基烷氧基、羟基烷氧基烷氧基、苯氧基或苯氧基烷基或其在苯氧基中的取代衍生物，但同种基团中不得超过一个为氢，其中一个或多个符号R3、R4或R5是氢原子或烷基或羟基或烷氧基或羟基烷基或羟基烷氧基或羟基烷氧基烷基或卤代烷基或羰基或羧基或酯基或酰胺基或腈基或磺酸基或卤素原子或硝基基团。
• Inhibitors of benzylaminoxidases, selective with respect to other aminoxidases
  申请人：CONSIGLIO NAZIONALE DELLE RICERCHE

  公开号：EP0210140A2

  公开（公告）日：1987-01-28

  Selective inhibitors of benzylaminoxidases, said inhibitors consisting of compounds of the general formula I wherein X is a group C-R4 or a nitrogen atom, R' and R2, which can be the same or different from each other, represent hydrogen, hydroxyl groups, alkoxyl groups, or alkyl, alkenyl, hydroxyalkyl, alkoxyalkyl, hydroxyalkoxyalkyl, hydroxyalkoxyl, alkoxyalkoxyl, hydroxyalkoxyalkxyl, phenoxyl or phenoxyalkyl groups or their substitution derivatives in the phenxyl group, provided that no more than one of the same be hydrogen, and one or more of the symbols R3, R4 or R5 are hydrogen atoms or alkyl or hydroxyl or alkoxyl or hydroxyalkyl or hydroxyalkoxyl or hydroxyalkoxyalkyl or haloalkyl or carboxylic or carboxylic or ester or amido or nitrile or sulfonic groups or halogen atoms or nitro groups.

  苄基氨基氧化酶的选择性抑制剂，所述抑制剂由通式 I 的化合物组成 其中 X 是基团 C-R4 或氮原子，R'和 R2 可以相同或不同，代表氢、羟基、烷氧基或烷基、烯基、羟烷基、烷氧基烷基、羟基烷氧基、羟基烷氧基、烷氧基烷氧基、羟基烷氧基烷氧基、苯氧基或苯氧基烷基或它们在苯氧基中的取代衍生物、只要其中不超过一个为氢，且一个或多个符号 R3、R4 或 R5 为氢原子或烷基或羟基或烷氧基或羟基烷基或羟基烷氧基或羟基烷氧基或卤代烷基或羧基或羧酸基或酯基或氨基或腈基或磺酸基或卤原子或硝基。
• US4888283A
  申请人：——

  公开号：US4888283A

  公开（公告）日：1989-12-19
• Synthesis of 2,6-disubstituted benzylamine derivatives as reversible selective inhibitors of copper amine oxidases
  作者：Francesco Lucchesini、Marco Pocci、Silvana Alfei、Vincenzo Bertini、Franca Buffoni

  DOI：10.1016/j.bmc.2014.01.037

  日期：2014.3

  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.
• 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。