2,6-bis(1-methylethoxy)benzylamine hydrochloride | 107694-35-9

• 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: 2,6-bis(1-methylethoxy)benzylamine hydrochloride
• 英文别名: [2,6-Di(propan-2-yloxy)phenyl]methanamine;hydrochloride
• CAS: 107694-35-9
• 化学式: C₁₃H₂₁NO₂*ClH
• 分子量: 259.776
• InChiKey: VIBDTWIMKIGBMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  44.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,6-bis(1-methylethoxy)benzaldehyde oxime 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 乙醚 为溶剂， 以53%的产率得到2,6-bis(1-methylethoxy)benzylamine hydrochloride
  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

• 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.