N-methyl-2,3,4-trimethoxyphenethylamine | 32042-11-8

• 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: N-methyl-2,3,4-trimethoxyphenethylamine
• 英文别名: N-Methyl-2,3,4-trimethoxyphenethylamin；Methyl[2-(2,3,4-trimethoxyphenyl)ethyl]amine；N-methyl-2-(2,3,4-trimethoxyphenyl)ethanamine
• CAS: 32042-11-8
• 化学式: C₁₂H₁₉NO₃
• 分子量: 225.288
• InChiKey: AAFDMAAXSJVSCP-UHFFFAOYSA-N

物化性质

• 沸点：
  305.8±37.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-2,3,4-trimethoxyphenethylamine 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 N-methyl-N-[2-(2,3,4-trimethoxyphenyl)ethyl]nitrous amide
  参考文献：
  名称：

  Synthesis, in Vitro Activity, and Three-Dimensional Quantitative Structure−Activity Relationship of Novel Hydrazine Inhibitors of Human Vascular Adhesion Protein-1

  摘要：

  Vascular adhesion protein-1 (VAP-1) belongs to the semicarbazide-sensitive amine oxidases (SSAOs) that convert amines into aldehydes. SSAOs are distinct from the mammalian monoamine oxidases (MAOs), but their substrate specificities are partly overlapping. VAP-1 has been proposed as a target for anti-inflammatory drug therapy because of its role in leukocyte adhesion to endothelium. Here, we describe the synthesis and in vitro activities of novel series of VAP-1 selective inhibitors. In addition, the molecular dynamics simulations performed for VAP-1 reveal that the movements of Met211, Ser496, and especially Leu469 can enlarge the ligand-binding pocket, allowing larger ligands than those seen in the crystal structures to bind. Combining the data from molecular dynamics simulations, docking, and in vitro measurements, the three-dimensional quantitative structure-activity relationship (3D QSAR) models for VAP-1 (q(LOO)(2): 0.636; r(2:) 0.828) and MAOs (q(LOO)(2): 0.749, r(2): 0.840) were built and employed in the development of selective VAP-1 inhibitors.

  DOI：

  10.1021/jm100337z
• 作为产物：
  描述：

  2-(2,3,4-三甲氧基苯基)乙胺 、 氯甲酸乙酯 生成 N-methyl-2,3,4-trimethoxyphenethylamine
  参考文献：
  名称：

  杂环化合物合成的研究。零件CCCLXXXV。1-（2-氨基苄基）-和1-（2-氨基苯乙基）-1,2,3,4-四氢异喹啉的Pschorr反应（总合成thalicsimidine）

  摘要：

  为了获得在8a-和2'-位之间偶联的二烯酮，1-（2-氨基-4,5-二甲氧基苄基）-1,2,3,4-四氢-6,8-二甲氧基-2-甲基异喹啉（ IIIa）和相应的5,6,7-三甲氧基-（IIIb）和6-羟基-7-甲氧基-（IIIc）衍生物进行Pschorr反应。化合物（IIIb）得到thalicsimidine（XIXa）；化合物（IIIc）得到3-硝基predicentrine（XIXb）和（2-羟基苄基）异喹啉（IIIj），以及正常产物（predicentrine）（XIXc）和二酚型化合物（Ib），收率很低。但是，1-（2-氨基-3,4,5-三甲氧基苯乙基）-（IIId）和1-（2-氨基-4-苄氧基-3,5-二甲氧基苯乙基）-1,2,3,4的Pschorr反应-四氢-6,7-二甲氧基-2-甲基异喹啉（IIIn）给出异常产物1'，2'，3'，4'-四氢-5,6,6'，7,7'-五甲氧基-2'-甲基螺[indan-1，

  DOI：

  10.1039/j39710001032

文献信息

• Novel calcium antagonists. Synthesis and structure-activity relationship studies of benzothiazoline derivatives
  作者：Koji Yamamoto、Masanobu Fujita、Keizo Tabashi、Yoichi Kawashima、Eishin Kato、Masayuki Oya、Tadashi Iso、Junichi Iwao

  DOI：10.1021/jm00400a006

  日期：1988.5

  A series of novel compounds having a benzothiazoline skeleton was studied for their structure-activity relationship (SAR) with respect to Ca2+ antagonistic activity. As test compounds, analogues of 3-acyl-2-arylbenzothiazolines (3) were synthesized. Benzothiazoline derivatives (3) exerted higher Ca2+ antagonistic activity than the corresponding thiazolidine derivatives (2). Effects of substituents

  研究了一系列具有苯并噻唑啉骨架的新型化合物的相对于Ca2 +拮抗活性的结构活性关系（SAR）。作为测试化合物，合成了3-酰基-2-芳基苯并噻唑啉的类似物（3）。苯并噻唑啉衍生物（3）比相应的噻唑烷衍生物（2）具有更高的Ca2 +拮抗活性。研究了取代基R1-R4，氨基烷氧基和R2的取代位置以及亚甲基链的长度对生物活性的影响。化合物4 [3-乙酰基-2- [5-甲氧基-2- [4- [N-甲基-N-（3,4,5-三甲氧基苯乙基）氨基]丁氧基]苯基]苯并噻唑啉盐酸盐]显示出有效的Ca2 +拮抗活性体外对Langendorff灌注兔心脏中Na +向内快速通道和Ca2 +向内缓慢通道的双重抑制。
• YAMAMOTO, KOJI;FUJITA, MASANOBU;TABASHI, KEIZO;KAWASHIMA, YOICHI;KATO, EI+, J. MED. CHEM., 31,(1988) N 5, 919-935
  作者：YAMAMOTO, KOJI、FUJITA, MASANOBU、TABASHI, KEIZO、KAWASHIMA, YOICHI、KATO, EI+

  DOI：——

  日期：——
• Synthesis, in Vitro Activity, and Three-Dimensional Quantitative Structure−Activity Relationship of Novel Hydrazine Inhibitors of Human Vascular Adhesion Protein-1
  作者：Elisa M. Nurminen、Marjo Pihlavisto、László Lázár、Zsolt Szakonyi、Ulla Pentikäinen、Ferenc Fülöp、Olli T. Pentikäinen

  DOI：10.1021/jm100337z

  日期：2010.9.9

  Vascular adhesion protein-1 (VAP-1) belongs to the semicarbazide-sensitive amine oxidases (SSAOs) that convert amines into aldehydes. SSAOs are distinct from the mammalian monoamine oxidases (MAOs), but their substrate specificities are partly overlapping. VAP-1 has been proposed as a target for anti-inflammatory drug therapy because of its role in leukocyte adhesion to endothelium. Here, we describe the synthesis and in vitro activities of novel series of VAP-1 selective inhibitors. In addition, the molecular dynamics simulations performed for VAP-1 reveal that the movements of Met211, Ser496, and especially Leu469 can enlarge the ligand-binding pocket, allowing larger ligands than those seen in the crystal structures to bind. Combining the data from molecular dynamics simulations, docking, and in vitro measurements, the three-dimensional quantitative structure-activity relationship (3D QSAR) models for VAP-1 (q(LOO)(2): 0.636; r(2:) 0.828) and MAOs (q(LOO)(2): 0.749, r(2): 0.840) were built and employed in the development of selective VAP-1 inhibitors.
• Studies on the syntheses of heterocyclic compounds. Part CCCLXXXV. Pschorr reactions of 1-(2-aminobenzyl)- and 1-(2-aminophenethyl)-1,2,3,4-tetrahydroisoquinolines (total synthesis of thalicsimidine)
  作者：T. Kametani、K. Takahashi、T. Sugahara、M. Koizumi、K. Fukumoto

  DOI：10.1039/j39710001032

  日期：——

  7-trimethoxy-(IIIb) and 6-hydroxy-7-methoxy-(IIIc) derivatives were subjected to the Pschorr reaction. Compound (IIIb) afforded thalicsimidine (XIXa); compound (IIIc) gave 3-nitropredicentrine (XIXb) and the (2-hydroxybenzyl)isoquinoline (IIIj), together with the normal product (predicentrine)(XIXc) and the diosphenol-type compound (Ib) in poor yield. However, Pschorr reactions of 1-(2-amino-3,4,5-trimethoxyphenethyl)-(IIId)

  为了获得在8a-和2'-位之间偶联的二烯酮，1-（2-氨基-4,5-二甲氧基苄基）-1,2,3,4-四氢-6,8-二甲氧基-2-甲基异喹啉（ IIIa）和相应的5,6,7-三甲氧基-（IIIb）和6-羟基-7-甲氧基-（IIIc）衍生物进行Pschorr反应。化合物（IIIb）得到thalicsimidine（XIXa）；化合物（IIIc）得到3-硝基predicentrine（XIXb）和（2-羟基苄基）异喹啉（IIIj），以及正常产物（predicentrine）（XIXc）和二酚型化合物（Ib），收率很低。但是，1-（2-氨基-3,4,5-三甲氧基苯乙基）-（IIId）和1-（2-氨基-4-苄氧基-3,5-二甲氧基苯乙基）-1,2,3,4的Pschorr反应-四氢-6,7-二甲氧基-2-甲基异喹啉（IIIn）给出异常产物1'，2'，3'，4'-四氢-5,6,6'，7,7'-五甲氧基-2'-甲基螺[indan-1，