6,7-dimethoxy-2-(2-phenylethyl)isoquinolinium chloride | 1293487-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6,7-dimethoxy-2-(2-phenylethyl)isoquinolinium chloride
• 英文别名: 6,7-Dimethoxy-2-(2-phenylethyl)isoquinolin-2-ium;chloride
• CAS: 1293487-93-0
• 化学式: C₁₉H₂₀NO₂*Cl
• 分子量: 329.826
• InChiKey: XMCKAETVEIWYGI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  22.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6,7-Dimethoxy-2-(2-phenylethyl)isoquinolin-2-ium;formate 在 calcium oxide 、 盐酸 作用下， 以 甲醇 、 水 、 乙醇 为溶剂， 反应 2.0h， 生成 6,7-dimethoxy-2-(2-phenylethyl)isoquinolinium chloride
  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

• Synthesis, structure–activity relationship and in vitro biological evaluation of N-arylethyl isoquinoline derivatives as Coxsackievirus B3 inhibitors
  作者：Yan-Xiang Wang、Yu-Huan Li、Ying-Hong Li、Rong-Mei Gao、Hui-Qiang Wang、Yan-Xin Liu、Li-Mei Gao、Qiao-Ni Lu、Jian-Dong Jiang、Dan-Qing Song

  DOI：10.1016/j.bmcl.2011.08.002

  日期：2011.10

  Currently, there is no approved antiviral drug for the infection caused by enteroviruses. A series of novel N-arylethyl isoquinoline derivatives defined with substituents on the ring A and C were designed, synthesized and evaluated in vitro for their activities against Coxsackievirus B3 (CVB3). The primary structure-activity relationship revealed that substituents on the ring A were not beneficial for the activity. Among these analogs synthesized, compound 7f bearing a methylenedioxy at the R(4) and R(5) positions afforded an anti-CVB3 activity and a reasonable selectivity index (SI = 26.8); furthermore, 7f exhibited a moderate activity against enterovirus 71 (EV71) with SI value of 9.0. Thus it has been selected as an anti-enteroviral lead compound for further investigation. (C) 2011 Elsevier Ltd. All rights reserved.