phenethyl-vanillyl-amine; hydrochloride | 68397-95-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: phenethyl-vanillyl-amine; hydrochloride
• 英文别名: Phenaethyl-vanillyl-amin; Hydrochlorid；2-Methoxy-4-{[(2-phenylethyl)amino]methyl}phenol--hydrogen chloride (1/1)；2-methoxy-4-[(2-phenylethylamino)methyl]phenol;hydrochloride
• CAS: 68397-95-5
• 化学式: C₁₆H₁₉NO₂*ClH
• 分子量: 293.793
• InChiKey: WDSGDZCHEDYADH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲酸 、 草酸醛 、 phenethyl-vanillyl-amine; hydrochloride 在 copper(II) sulfate 作用下， 反应 5.0h， 生成 7-Methoxy-2-(2-phenylethyl)isoquinolin-2-ium-6-ol;formate
  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：

  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

文献信息

• CASADIO S.; COUSSE H.; MOUZIN G.; STENGER A.; CHARVERON M.; VILAIN P.; LA+, BOLL. CHIM. FARM., 1978, 117, NO 2, 83-89
  作者：CASADIO S.、 COUSSE H.、 MOUZIN G.、 STENGER A.、 CHARVERON M.、 VILAIN P.、 LA+

  DOI：——

  日期：——
• 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.