2,3,4-(MeO)3C6H2CHNCH3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,3,4-(MeO)3C6H2CHNCH3
• 英文别名: N-methyl-1-(2,3,4-trimethoxyphenyl)methanimine
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: NEZHTXQBNGVEPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,4-(MeO)3C6H2CHNCH3 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以100%的产率得到N-methyl-N-[(2,3,4-trimethoxyphenyl)methyl]amine
  参考文献：
  名称：

  Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[ω-(benzylmethylamino)alkoxy]xanthen-9-ones

  摘要：

  In this work, we further investigated a previously introduced class of cholinesterase inhibitors. The removal of the carbarnic function from the lead compound xanthostigmine led to a reversible cholinesterase inhibitors 3. Some new 3-[omega-(benzylmethylamino)alkoxy]xanthen-9-one analogs were designed, synthesized, and evaluated for their inhibitory activity against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The length of the alkoxy chain of compound 3 was increased and different substituents were introduced. From the IC50 values, it clearly appears that the carbamic residue is crucial to obtain highly potent AChE inhibitors. On the other hand, peculiarity of these compounds is the high selectivity toward BuChE with respect to AChE, being compound 12 the most selective one (6000-fold). The development of selective BuChE inhibitors may be of great interest to clarify the physiological role of this enzyme and to provide novel therapeutics for various diseases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.026
• 作为产物：
  描述：

  甲胺 、 2,3,4-三甲氧基苯甲醛 以 乙醇 为溶剂， 以90%的产率得到2,3,4-(MeO)3C6H2CHNCH3
  参考文献：
  名称：

  Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[ω-(benzylmethylamino)alkoxy]xanthen-9-ones

  摘要：

  In this work, we further investigated a previously introduced class of cholinesterase inhibitors. The removal of the carbarnic function from the lead compound xanthostigmine led to a reversible cholinesterase inhibitors 3. Some new 3-[omega-(benzylmethylamino)alkoxy]xanthen-9-one analogs were designed, synthesized, and evaluated for their inhibitory activity against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The length of the alkoxy chain of compound 3 was increased and different substituents were introduced. From the IC50 values, it clearly appears that the carbamic residue is crucial to obtain highly potent AChE inhibitors. On the other hand, peculiarity of these compounds is the high selectivity toward BuChE with respect to AChE, being compound 12 the most selective one (6000-fold). The development of selective BuChE inhibitors may be of great interest to clarify the physiological role of this enzyme and to provide novel therapeutics for various diseases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.026

文献信息

• The First Crystal and Molecular Structure of asyn-Acetato-Bridged Dinuclear Cyclometallated Complex [Pd{2,3,4-(MeO)3C6HC(H)=NCH2CH2OH}(μ-OAc)]2
  作者：Alberto Fernández、Digna Vázquez-García、Jesús J. Fernández、Margarita López-Torres、Antonio Suárez、Samuel Castro-Juiz、José M. Vila

  DOI：10.1002/1099-0682(200209)2002:9<2389::aid-ejic2389>3.0.co;2-m

  日期：2002.9

  4-(MeO)3C6H2C(H)=NR (R = CH2CH2OH, 1; R = Me, 17; R = Et, 18; R = Pr, 19; R = tBu, 20) with palladium(II) acetate in toluene gave the dinuclear cyclometallated complexes [Pd2,3,4-(MeO)3C6HC(H)=NR}(μ-O2CMe)]2 (R = CH2CH2OH, 2; R = Me, 21; R = Et, 22; R = Pr, 23; R = tBu, 24), with the ligand bonded to the palladium atom through the imine nitrogen and the C6 carbon atoms. The 1H and 13C1H} NMR spectra of the

  席夫碱配体的处理 2,3,4-(MeO)3C6H2C(H)=NR (R = CH2CH2OH, 1; R = Me, 17; R = Et, 18; R = Pr, 19; R = tBu, 20) 在甲苯中用乙酸钯 (II) 得到双核环金属化配合物 [Pd2,3,4-(MeO)3C6HC(H)=NR}(μ-O2CMe)]2 (R = CH2CH2OH, 2; R = Me, 21; R = Et, 22; R = Pr, 23; R = tBu, 24)，配体通过亚胺氮和 C6 碳原子与钯原子键合。配合物的 1H 和 13C1H} NMR 谱表明溶液中存在反异构体和顺异构体。anti/syn 比率随溶剂和亚胺氮取代基 R 的性质而变化。具有大体积 tBu 基团的配合物 24 在氯仿中显示出 28:1 的比率，而体积较小的取代配合物显示出较低的比率。描述了配合物 2 顺式异构体的 X 射线晶体结构。乙酰基桥连络合物
• Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[ω-(benzylmethylamino)alkoxy]xanthen-9-ones
  作者：Lorna Piazzi、Federica Belluti、Alessandra Bisi、Silvia Gobbi、Stefano Rizzo、Manuela Bartolini、Vincenza Andrisano、Maurizio Recanatini、Angela Rampa

  DOI：10.1016/j.bmc.2006.09.026

  日期：2007.1.1

  In this work, we further investigated a previously introduced class of cholinesterase inhibitors. The removal of the carbarnic function from the lead compound xanthostigmine led to a reversible cholinesterase inhibitors 3. Some new 3-[omega-(benzylmethylamino)alkoxy]xanthen-9-one analogs were designed, synthesized, and evaluated for their inhibitory activity against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The length of the alkoxy chain of compound 3 was increased and different substituents were introduced. From the IC50 values, it clearly appears that the carbamic residue is crucial to obtain highly potent AChE inhibitors. On the other hand, peculiarity of these compounds is the high selectivity toward BuChE with respect to AChE, being compound 12 the most selective one (6000-fold). The development of selective BuChE inhibitors may be of great interest to clarify the physiological role of this enzyme and to provide novel therapeutics for various diseases. (c) 2006 Elsevier Ltd. All rights reserved.