6,7-Dimethoxy-1-(2-naphthylmethyl)-isochinolin | 112504-23-1

• 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-1-(2-naphthylmethyl)-isochinolin
• 英文别名: 6,7-dimethoxy-1-(2-naphthylmethyl)-isoquinoline；6,7-dimethoxy-1-(naphthalen-2-ylmethyl)isoquinoline
• CAS: 112504-23-1
• 化学式: C₂₂H₁₉NO₂
• 分子量: 329.398
• InChiKey: NLHBPERXXHWVTF-UHFFFAOYSA-N

物化性质

• 熔点：
  113-115 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  511.2±45.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-Dimethoxy-1-(2-naphthylmethyl)-isochinolin 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.25h， 生成 6,7-dimethoxy-2-methyl-1-(naphthalen-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis and Radioligand Binding Studies of Methoxylated 1,2,3,4-Tetrahydroisoquinolinium Derivatives as Ligands of the Apamin-Sensitive Ca²⁺-Activated K⁺ Channels

  摘要：

  Several methoxylated 1,2,3,4-tetrahydroisoquinoliniums derived from N-methyl-laudanosine and N-methyl-noscapine were synthesized and evaluated for their affinity for apamin-sensitive binding sites. The quaternary ammonium derivatives have a higher affinity with regard to the tertiary amines. 6,7-Dimethoxy analogues possess a higher affinity than the 6,8- and 7,8- dimethoxy isomers. A 3,4-dimethoxybenzyl or a 2-naphthylmethyl moiety in C-1 position are more favorable than a 3,4-dimethoxyphenethyl group. Smaller groups such as propyl or isobutyl are unfavorable. In 6,7-dimethoxy analogues, increasing the size and lipophilicity with a naphthyl group in the C-1 position leads to a slight increase of affinity, while the same group in the 6,7,8- trimethoxy series is less favorable. The 6,7,8- trimethoxy derivative 3f is the first tertiary amine in the series to possess an affinity close to that of N-methyl-laudanosine and N-methyl-noscapine. Moreover, electrophysiological studies show that the most effective compound 4f blocks the apamin-sensitive afterhyperpolarization in rat dopaminergic neurons.

  DOI：

  10.1021/jm0607395
• 作为产物：
  描述：

  2-benzoyl-1-cyano-6,7-dimethoxy-1,2-dihydroisoquinoline 在 苄基三甲基氢氧化铵 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 6,7-Dimethoxy-1-(2-naphthylmethyl)-isochinolin
  参考文献：
  名称：

  二氢异喹啉重排，第 37 版。具有庞大的 C-1 取代基作为 1,2-二氢异喹啉的前体的异喹啉盐的合成

  摘要：

  Reissert 化合物 1 烷基化得到化合物 2a-2d。皂化后，这些得到异喹啉 3a-3d，其与甲基碘反应形成亚胺碘化物 4a-4d。

  DOI：

  10.1002/ardp.19873200405

文献信息

• 1,2,3-Triazole-Mediated Synthesis of 1-Methyleneisoquinolines: A Three-Step Synthesis of Papaverine and Analogues
  作者：Tomas Opsomer、Max Van Hoof、Andrea D’Angelo、Wim Dehaen

  DOI：10.1021/acs.orglett.0c01069

  日期：2020.5.1

  A metal-free three-step synthesis toward functionalized 1-methyleneisoquinolines from readily available substrates is reported. First, acetal-containing 1,2,3-triazoles were prepared via a high-yielding triazolization reaction and quantitatively converted into triazolo[5,1-a]isoquinolines. Next, the acid-promoted ring opening of these fused triazoles was studied in order to obtain coupling to a diverse

  据报道，从容易获得的底物向官能化的1-亚甲基异喹啉进行无金属的三步合成。首先，通过高产率的三唑化反应制备含缩醛的1,2,3-三唑，并将其定量转化为三唑并[5,1-a]异喹啉。接下来，对这些稠合三唑的酸促进的开环进行了研究，以便获得与多种亲核试剂的偶联，包括碳亲核试剂，如藜芦醛。借助无水条件下的非亲核强酸，合成了一系列前所未有的异喹啉和咪唑并[5,1-a]异喹啉。
• KNABE J.; GRUNEWALD F. -J., ARCH. PHARM., 320,(1987) N 4, 303-308
  作者：KNABE J.、 GRUNEWALD F. -J.

  DOI：——

  日期：——
• DERIVATIVES OF PAPAVERINE THAT ARE EFFECTIVE HYPOXIC TUMOR RADIOSENSITIZERS
  申请人：Ohio State Innovation Foundation

  公开号：US20210163453A1

  公开（公告）日：2021-06-03

  Disclosed herein are compounds, compositions, and methods for inhibiting mitochondrial oxygen consumption in a cancerous tissue. The compounds, compositions, and methods can be used to treat a subject with hypoxic cancerous tissue.
• [EN] DERIVATIVES OF PAPAVERINE THAT ARE EFFECTIVE HYPOXIC TUMOR RADIOSENSITIZERS<br/>[FR] DÉRIVÉS DE PAPAVÉRINE QUI SONT DES RADIOSENSIBILISATEURS DE TUMEURS HYPOXIQUES EFFICACES
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：WO2020023537A1

  公开（公告）日：2020-01-30

  Disclosed herein are compounds, compositions, and methods for inhibiting mitochondrial oxygen consumption in a cancerous tissue. The compounds, compositions, and methods can be used to treat a subject with hypoxic cancerous tissue.