N-(4-hydroxy-3-methoxybenzylidene)-2-phenylethanamine | 115372-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(4-hydroxy-3-methoxybenzylidene)-2-phenylethanamine
• 英文别名: N-(4-hydroxy-3-methoxybenzylidene)phenethylamine；2-methoxy-4-(2-phenylethyliminomethyl)phenol
• CAS: 115372-26-4
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: VLYKPQQFFJZELT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-hydroxy-3-methoxybenzylidene)-2-phenylethanamine 在 sodium tetrahydroborate 、 盐酸 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 phenethyl-vanillyl-amine; hydrochloride
  参考文献：
  名称：

  Synthesis and structure–activity relationship of N-(2-arylethyl) isoquinoline derivatives as human scavenger receptor CD36 antagonists

  摘要：

  By using human scavenger receptor CD36 as the target, twenty-five N-(2-arylethyl) isoquinoline derivatives were designed, synthesized and evaluated for their antagonistic activities for CD36-oxidatively low density lipoprotein (oxLDL) binding. The primary analysis of structure-activity relationship (SAR) indicated a methoxyl at the 7-position and a hydroxyl at the 6- or 8-position could afford good activities. Among these analogs, compounds 7e and 7t showed the potential CD36 antagonistic activities with IC(50) values of 0.2 and 0.8 mu g/mL, respectively. Furthermore, both of them could effectively inhibit oxLDL uptake in insect Sf9 cells overexpressing human CD36, and thus have been selected for further investigation. We consider N-(2-arylethyl) isoquinoline analogs to be a family of novel CD36 antagonists. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.022
• 作为产物：
  描述：

  香草醛 、 2-苯乙胺 以 甲醇 为溶剂， 反应 48.0h， 生成 N-(4-hydroxy-3-methoxybenzylidene)-2-phenylethanamine
  参考文献：
  名称：

  芳环上的羟基在β-苯乙胺与不可烯化醛的反应活性和选择性中的作用

  摘要：

  研究了羟基对β-苯乙胺芳环与不可烯化醛反应的影响。计算计算表明，羟基化程度会在环的活化方式（不同的反应途径）和氮原子的亲核性（不同的反应产率）之间产生差异。在与甲醛反应中获得了环状缩醛，苯并恶嗪酮或四氢异喹啉，在与其他不可烯化的醛反应中产生了席夫氏碱或四氢异喹啉。所获得的产物取决于起始苯乙胺的环的羟基化程度。

  DOI：

  10.1007/s11164-015-1987-4

文献信息

• Synthesis and structure–activity relationship of N-(2-arylethyl) isoquinoline derivatives as human scavenger receptor CD36 antagonists
  作者：Yan-Xiang Wang、Li Wang、Yan-Ni Xu、Ying-Hong Li、Jian-Dong Jiang、Shu-Yi Si、Yang-Biao Li、Gang Ren、Yong-Qiang Shan、Bin Hong、Dan-Qing Song

  DOI：10.1016/j.ejmech.2011.01.022

  日期：2011.4

  By using human scavenger receptor CD36 as the target, twenty-five N-(2-arylethyl) isoquinoline derivatives were designed, synthesized and evaluated for their antagonistic activities for CD36-oxidatively low density lipoprotein (oxLDL) binding. The primary analysis of structure-activity relationship (SAR) indicated a methoxyl at the 7-position and a hydroxyl at the 6- or 8-position could afford good activities. Among these analogs, compounds 7e and 7t showed the potential CD36 antagonistic activities with IC(50) values of 0.2 and 0.8 mu g/mL, respectively. Furthermore, both of them could effectively inhibit oxLDL uptake in insect Sf9 cells overexpressing human CD36, and thus have been selected for further investigation. We consider N-(2-arylethyl) isoquinoline analogs to be a family of novel CD36 antagonists. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Role of hydroxyl groups on the aromatic ring in the reactivity and selectivity of the reaction of β-phenylethylamines with non-enolizable aldehydes
  作者：Rodolfo Quevedo、Christian Díaz-Oviedo、Yovanny Quevedo-Acosta

  DOI：10.1007/s11164-015-1987-4

  日期：2015.12

  The influence of hydroxyl groups on the β-phenylethylamine aromatic ring was studied during its reaction with non-enolizable aldehydes. Computational calculations established that the degree of hydroxylation generates differences in the activation patterns of the ring (different reaction pathways) and in the nucleophilicity of the nitrogen atoms (different reaction yields). Cyclic aminals, benzoxazinephanes

  研究了羟基对β-苯乙胺芳环与不可烯化醛反应的影响。计算计算表明，羟基化程度会在环的活化方式（不同的反应途径）和氮原子的亲核性（不同的反应产率）之间产生差异。在与甲醛反应中获得了环状缩醛，苯并恶嗪酮或四氢异喹啉，在与其他不可烯化的醛反应中产生了席夫氏碱或四氢异喹啉。所获得的产物取决于起始苯乙胺的环的羟基化程度。