8-(2-phenylethyl)[1,3]dioxolo[4,5-h]isoquinolin-8-ium chloride | 1338239-53-4

• 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: 8-(2-phenylethyl)[1,3]dioxolo[4,5-h]isoquinolin-8-ium chloride
• 英文别名: 8-(2-Phenylethyl)-[1,3]dioxolo[4,5-h]isoquinolin-8-ium;chloride
• CAS: 1338239-53-4
• 化学式: C₁₈H₁₆NO₂*Cl
• 分子量: 313.784
• InChiKey: VCAHVJMJFPRGJI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  在 calcium oxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 以52%的产率得到8-(2-phenylethyl)[1,3]dioxolo[4,5-h]isoquinolin-8-ium chloride
  参考文献：
  名称：

  Synthesis, structure–activity relationship and in vitro biological evaluation of N-arylethyl isoquinoline derivatives as Coxsackievirus B3 inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.08.002

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.