5-(4'-hydroxy-5'-methoxynaphthalen-1'-yl)-3,3-dimethyl-3,4-dihydroisoquinolin-8-ol | 1257243-63-2

• 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: 5-(4'-hydroxy-5'-methoxynaphthalen-1'-yl)-3,3-dimethyl-3,4-dihydroisoquinolin-8-ol
• 英文别名: 5-(4-hydroxy-5-methoxy-1-naphthyl)-3,3-dimethyl-4H-isoquinolin-8-ol；5-(4-hydroxy-5-methoxynaphthalen-1-yl)-3,3-dimethyl-4H-isoquinolin-8-ol
• CAS: 1257243-63-2
• 化学式: C₂₂H₂₁NO₃
• 分子量: 347.414
• InChiKey: NINNQOHCEJWOPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4'-hydroxy-5'-methoxynaphthalen-1'-yl)-3,3-dimethyl-3,4-dihydroisoquinolin-8-ol 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以44%的产率得到5-(4'-hydroxy-5'-methoxynaphthalen-1'-yl)-3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol
  参考文献：
  名称：

  QSAR guided synthesis of simplified antiplasmodial analogs of naphthylisoquinoline alkaloids

  摘要：

  Naphthylisoquinoline alkaloids have attracted considerable interest because of their intriguing structure, their unique biosynthetic origin, and their biological activities against several pathogens causing tropical diseases. Their promising pharmacologic properties make them suitable lead structures for new agents, in particular against malaria. Since these natural products are not easy to isolate in sufficient quantities or to synthesize stereoselectively, quantitative structure activity relationship studies were accomplished to find new antiplasmodial analogs that are structurally related to the naturally occurring naphthylisoquinoline alkaloids, but more easily accessible, more active against Plasmodium falciparum, and, last but not least, less toxic. We report on the synthesis of several simplified compounds by a Suzuki coupling between the naphthalene and the isoquinoline moieties and on their activities against different pathogens causing infectious diseases. Some structures were found to exhibit excellent and selective activities against P. falciparum in vitro. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.062
• 作为产物：
  描述：

  5-(4'-isopropoxy-5'-methoxynaphthalen-1'-yl)-3,3-dimethyl-3,4-dihydroisoquinolin-8-ol 在 三氯化硼 、 甲醇 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 以68%的产率得到5-(4'-hydroxy-5'-methoxynaphthalen-1'-yl)-3,3-dimethyl-3,4-dihydroisoquinolin-8-ol
  参考文献：
  名称：

  QSAR guided synthesis of simplified antiplasmodial analogs of naphthylisoquinoline alkaloids

  摘要：

  Naphthylisoquinoline alkaloids have attracted considerable interest because of their intriguing structure, their unique biosynthetic origin, and their biological activities against several pathogens causing tropical diseases. Their promising pharmacologic properties make them suitable lead structures for new agents, in particular against malaria. Since these natural products are not easy to isolate in sufficient quantities or to synthesize stereoselectively, quantitative structure activity relationship studies were accomplished to find new antiplasmodial analogs that are structurally related to the naturally occurring naphthylisoquinoline alkaloids, but more easily accessible, more active against Plasmodium falciparum, and, last but not least, less toxic. We report on the synthesis of several simplified compounds by a Suzuki coupling between the naphthalene and the isoquinoline moieties and on their activities against different pathogens causing infectious diseases. Some structures were found to exhibit excellent and selective activities against P. falciparum in vitro. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.062

文献信息

• QSAR guided synthesis of simplified antiplasmodial analogs of naphthylisoquinoline alkaloids
  作者：Gerhard Bringmann、Sebastian K. Bischof、Steffen Müller、Tanja Gulder、Christian Winter、August Stich、Heidrun Moll、Marcel Kaiser、Reto Brun、Jan Dreher、Knut Baumann

  DOI：10.1016/j.ejmech.2010.08.062

  日期：2010.11

  Naphthylisoquinoline alkaloids have attracted considerable interest because of their intriguing structure, their unique biosynthetic origin, and their biological activities against several pathogens causing tropical diseases. Their promising pharmacologic properties make them suitable lead structures for new agents, in particular against malaria. Since these natural products are not easy to isolate in sufficient quantities or to synthesize stereoselectively, quantitative structure activity relationship studies were accomplished to find new antiplasmodial analogs that are structurally related to the naturally occurring naphthylisoquinoline alkaloids, but more easily accessible, more active against Plasmodium falciparum, and, last but not least, less toxic. We report on the synthesis of several simplified compounds by a Suzuki coupling between the naphthalene and the isoquinoline moieties and on their activities against different pathogens causing infectious diseases. Some structures were found to exhibit excellent and selective activities against P. falciparum in vitro. (C) 2010 Elsevier Masson SAS. All rights reserved.