(R)-5-bromo-8-methoxy-1,3-dimethyl-3,4-dihydroisoquinoline | 1257243-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: (R)-5-bromo-8-methoxy-1,3-dimethyl-3,4-dihydroisoquinoline
• 英文别名: (3R)-5-bromo-8-methoxy-1,3-dimethyl-3,4-dihydroisoquinoline
• CAS: 1257243-70-1
• 化学式: C₁₂H₁₄BrNO
• 分子量: 268.153
• InChiKey: XNOYHJHAGGFXKU-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-5-bromo-8-methoxy-1,3-dimethyl-3,4-dihydroisoquinoline 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以92%的产率得到5-bromo-8-methoxy-1S,3R-dimethyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  刚果藤本植物大鳞中的Dioncophyllines C 2，D 2和F及其相关的萘基异喹啉生物碱对恶性疟原虫和多发性骨髓瘤和白血病细胞系具有有效活性

  摘要：

  从最近描述的刚果藤上藤本Ancistrocladus ileboensis中分离到了第一个5,8'偶合的二糖类生物碱Dioncophylline F（1）（即在C-6处没有氧功能，在C-3处具有R构型）。两个另外，同样地双钩叶科型，生物碱，所述dioncophyllinesÇ 2（2）和d 2（3），进行了鉴定，与钩枝藤科型化合物ancistrocladisine B（沿4），这是在C-6和含氧小号-配置在C-3。新化合物的结构通过光谱，化学和手性方法确定。的立体结构通过全合成进一步证实了1。由于缺少在其联芳基轴上邻位的甲基，二oncophylline F（1）和7,8'偶联的dioncophylline D 2（3）都以成对的半稳定态出现，因此，它们之间缓慢地相互转化。非对映异构体，而具有5，1'-键的二茶碱C 2（2）在轴上构型稳定。从ileboensis中分离出八种已知的萘异喹啉，其中二茶碱A（P

  DOI：

  10.1021/acs.jnatprod.6b00967
• 作为产物：
  描述：

  (R)-4-bromo-3-(2'-acetamidoprop-1'-yl)anisole 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以68%的产率得到(R)-5-bromo-8-methoxy-1,3-dimethyl-3,4-dihydroisoquinoline
  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