3,4-二甲氧基-N,N-二甲基-1-菲乙胺 | 5531-98-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 6,6a-仲卟啉
• 中文名称: 3,4-二甲氧基-N,N-二甲基-1-菲乙胺
• 中文别名: 芒籽宁
• 英文名称: picrate d' athérosperminine
• 英文别名: 1-[2-(N,N-dimethylaminoethyl)]-3,4-dimethoxyphenanthrene；phenanthrenes atherosperminine；O-methylargentinine；Atherosperminine；[2-(3,4-dimethoxy-[1]phenanthryl)-ethyl]-dimethyl-amine；[2-(3,4-Dimethoxy-[1]phenanthryl)-aethyl]-dimethyl-amin；2-(3,4-dimethoxyphenanthren-1-yl)-N,N-dimethylethanamine
• CAS: 5531-98-6
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: UZZFAUDNCIFFPM-UHFFFAOYSA-N

物化性质

• 熔点：
  199 °C
• 沸点：
  466.1±35.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2922199090

制备方法与用途

生物活性

Atherosperminine（Atherospermine）是一种天然的生物碱。在体外实验中，它表现出对疟原虫的抗活性，其IC50值为5.80 μM。此外，Atherosperminine 是一种优秀的还原剂，并且具有螯合金属的能力。该化合物还显示出DPPH自由基清除活性，其IC50值为29.56 µg/mL。另外，Atherosperminine 对气管具有非特异性的松弛作用。

靶点

• IC50: 5.80 μM (恶性疟原虫, K1菌株)

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基-N,N-二甲基-1-菲乙胺 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到1-(2-Dimethylaminoethyl)-3,4-dihydroxyphenanthren
  参考文献：
  名称：

  3,4-Dihydroxy- and 3,4-methylenedioxy- phenanthrene-type alkaloids with high selectivity for D2 dopamine receptor

  摘要：

  Dopamine-mediated neurotransmission plays an important role in relevant psychiatric and neurological disorders. Nowadays, there is an enormous interest in the development of new drugs acting at the dopamine receptors (DR) as potential new targets for the treatment of schizophrenia or Parkinson's disease. Previous studies have revealed that isoquinoline compounds such as tetrahydroisoquinolines (THIQs) can behave as selective D-2 dopaminergic alkaloids. In the present study we have synthesized five aporphine compounds and five phenanthrene alkaloids and evaluated their potential dopaminergic activity. Binding studies on rat striatal membranes were used to evaluate their affinity and selectivity towards D-1 and D-2 DR. Phenanthrene type alkaloids, in particular the 3,4-dihydroxy- and 3,4-methylenedioxy derivatives, displayed high selectivity towards D-2 DR. Therefore, they are potential candidates to be used in the treatment of schizophrenia (antagonists) or Parkinson's disease (agonists) due to their scarce D-1 DR-associated side effects. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.078
• 作为产物：
  描述：

  N-carbethoxy-2-(3',4'-dimethoxy-1'-phenanthryl)ethylamine 在 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 3,4-二甲氧基-N,N-二甲基-1-菲乙胺
  参考文献：
  名称：

  菲生物碱的新全合成

  摘要：

  我们描述了基于通过简单、有效的新方法制备的芪化合物的光环化的菲生物碱的新合成。它允许制备在其侧链中具有伯胺基团的菲化合物。关键词：生物碱，菲，芪，光环化。

  DOI：

  10.1139/v90-151

文献信息

• Radical cyclization to dibenzo[de,g]chromanones. A new synthesis of phenanthrene compounds.
  作者：Juan C. Estévez、M.Carmen Villaverde、Ramón J. Estévez、Luis Castedo

  DOI：10.1016/s0040-4020(01)86354-7

  日期：1993.3

  We describe the radical cyclization of bromobenzylisochromanones to afford the novel dibenzo[de,g]chromanones. Opening the lactone ring of the latter allows the preparation of phenanthrene alkaloids and 1-phenanthrenylacetic acids.

  我们描述了溴苄基异苯并二氢呋喃酮的自由基环化作用，以提供新型的二苯并[de，g]苯并二氢呋喃酮。打开后者的内酯环可以制备菲生物碱和1-菲基乙酸。
• Reductive dicarbonyl coupling with low-valent titanium reagents: a new entry to phenanthrene alkaloids
  作者：Julio A. Seijas、Angel R. de Lera、M. Carmen Villaverde、Luis Castedo

  DOI：10.1039/c39850000839

  日期：——

  A new and direct synthesis of phenanthrene alkaloids using a low-valent titanium reagent is described which is compatible with ethoxycarbonyl as the N-protecting group.

  描述了使用低价钛试剂的新的直接合成菲生物碱的方法，该试剂与乙氧基羰基作为N-保护基团相容。
• A new convenient synthesis of phenanthrene alkaloids from 1-arylmethyl-1,2,3,4-tetrahydroisoquinolines
  作者：S.V. Kini、M.M.V. Ramana

  DOI：10.1016/j.tetlet.2004.03.127

  日期：2004.5

  1-arylmethyl-1,2,3,4-tetrahydro-2,2-dimethylisoquinolinium iodides with methanolic KOH gave stilbene derivatives, for example, (E)-N-22-[2-(phenyl)ethenyl]-4,5-dimethoxyphenyl}ethyl-N,N-dimethylamine. Photochemical electrocyclization of these stilbenes afforded the corresponding phenanthrene alkaloids/phenanthrene derivatives.

  霍夫曼用甲醇KOH降解1-芳基甲基1,2,3,4-四氢-2,2-二甲基异喹啉碘化物，得到二苯乙烯衍生物，例如（E）-N -2 2- [2-（2-苯基）乙烯基] ] -4，5-二甲氧基苯基}乙基-N，N-二甲基胺。这些苯乙烯的光化学电环化得到相应的菲生物碱/菲衍生物。
• Antibacterial and antifungal activity of liriodenine and related oxoaporphine alkaloids
  作者：Charles D. Hufford、Alpana S. Sharma、Babajide O. Oguntimein

  DOI：10.1002/jps.2600691016

  日期：1980.10

  Liriodenine was evaluated for its antibacterial and antifungal activity against several microorganisms. Other related oxoaporphine alkaloids also were evaluated. Attempts to prepare oxoaporphine alkaloids from N-acetylnoraporphines were unsuccessful, but an unexpected phenanthrene alkaloid was obtained. A novel N-demethylation reaction was noted when oxogaucine methiodide and liriodenine methiodide

  评估了鹅绒素对多种微生物的抗菌和抗真菌活性。还评估了其他相关的氧磷卟啉生物碱。从N-乙酰基诺拉非芬制备氧杂卟啉生物碱的尝试未成功，但获得了意想不到的菲生物碱。当用氧化铝处理氧高aucine甲硫酮和去氧里丁烯二甲硫醚时，发现了新的N-脱甲基反应。
• Lu, Sheng-Teh; Wu, Yang-Chang, Heterocycles, 1985, vol. 23, # 12, p. 3085 - 3094
  作者：Lu, Sheng-Teh、Wu, Yang-Chang

  DOI：——

  日期：——