(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-[5-(6-methoxynaphthalen-2-yl)-furan-2-yl]-methanone | 1424834-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-[5-(6-methoxynaphthalen-2-yl)-furan-2-yl]-methanone
• CAS: 1424834-85-4
• 化学式: C₂₇H₂₅NO₅
• 分子量: 443.499
• InChiKey: CDKXCNJKCVAYIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.14
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-[5-(6-methoxynaphthalen-2-yl)-furan-2-yl]-methanone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以33%的产率得到6,7-dimethoxy-2-[[5-(6-methoxynaphthalen-2-yl)furan-2-yl]methyl]-3,4-dihydro-1H-isoquinoline
  参考文献：
  名称：

  Naphthalenyl derivatives for hitting P-gp/MRP1/BCRP transporters

  摘要：

  Substituted naphthalenyl derivatives bearing oxazole, or thiazole or furyl heteronuclei have been carried out as bioisosters of aryl-oxazoles and -thiazoles derivatives previously reported in order to investigate the role of the hindrance on the activity towards P-gp/BCRP/and MRP1 transporters. In addition, the role of naphthalenyl group to modulate P-gp intrinsic activity of these compounds was ascertained.The results demonstrated that all naphthalenyl derivatives displayed comparable P-gp activity with respect to lead compounds previously characterized in our SAR studies but were less active towards BCRP and MRP1 pumps. In terms of intrinsic activity, the replacement of aryl with naphthalenyl moiety led to P-gp inhibitors, unambiguous or ambiguous substrates on the base of the heteronucleus and the substituent on the naphthalenyl fragment. Indeed, oxazole derivatives were: inhibitors (R = H, F, OH), unambiguous substrates (R = OCH3), or ambiguous substrate (R = Br); thiazole derivatives were: unambiguous substrates (R = OCH3, Br), or ambiguous substrates (R = H, F). Finally furyl derivatives were ambiguous substrates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.021
• 作为产物：
  描述：

  6-甲氧基萘-2-硼酸 在 potassium carbonate 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.5h， 生成 (6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-[5-(6-methoxynaphthalen-2-yl)-furan-2-yl]-methanone
  参考文献：
  名称：

  Naphthalenyl derivatives for hitting P-gp/MRP1/BCRP transporters

  摘要：

  Substituted naphthalenyl derivatives bearing oxazole, or thiazole or furyl heteronuclei have been carried out as bioisosters of aryl-oxazoles and -thiazoles derivatives previously reported in order to investigate the role of the hindrance on the activity towards P-gp/BCRP/and MRP1 transporters. In addition, the role of naphthalenyl group to modulate P-gp intrinsic activity of these compounds was ascertained.The results demonstrated that all naphthalenyl derivatives displayed comparable P-gp activity with respect to lead compounds previously characterized in our SAR studies but were less active towards BCRP and MRP1 pumps. In terms of intrinsic activity, the replacement of aryl with naphthalenyl moiety led to P-gp inhibitors, unambiguous or ambiguous substrates on the base of the heteronucleus and the substituent on the naphthalenyl fragment. Indeed, oxazole derivatives were: inhibitors (R = H, F, OH), unambiguous substrates (R = OCH3), or ambiguous substrate (R = Br); thiazole derivatives were: unambiguous substrates (R = OCH3, Br), or ambiguous substrates (R = H, F). Finally furyl derivatives were ambiguous substrates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.021