8-[2-(methylamino)-ethyl]-phenanthrene-3,4-dioxide | 1334547-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-[2-(methylamino)-ethyl]-phenanthrene-3,4-dioxide
• 英文别名: Apomorphine Phenanthrene Dione；8-[2-(methylamino)ethyl]phenanthrene-3,4-dione
• CAS: 1334547-61-3
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: XARFTOZXPPODOO-UHFFFAOYSA-N

物化性质

• 沸点：
  466.6±45.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  盐酸去水吗啡 在 氧气 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 12.03h， 以47%的产率得到oxoapomorphine
  参考文献：
  名称：

  Extensive study of the autooxidation products of apomorphine and its pharmacologically active derivatives

  摘要：

  The autooxidation phenomenon of apomorphine and the products of this procedure were analytically and pharmacologically studied, however we found that there have been some unclarified details of this filed. Therefore the synthesis and structure of the autooxidation products of three clinically and pharmacologically relevant aporphinoids (apomoprine, N-propyl-norapomorphine and 2-hydroxy-N-propyl-norapomorphine) were thoroughly investigated. The autooxidation of apomorphine achieved at physiological pH resulted two products; one of them is the known tetracyclic, tertiary amino ortho quinone and the hitherto unknown, fluorescent, derivatized phenanthrene-3,4-quinone. Under the same conditions N-propyl congeners resulted only the expected 1,2-dione products. The analytical structure elucidation involved the full H-1 and C-13 NMR assignment, UV and IR characterizations of the four isolated ortho quinone-type products exploiting the possibilities of DFT calculations for geometry optimization. NMR and IR simulations. The phenanthrene-3,4-quinone compound can be relevant in further pharmacological studies of aporphine-related oxidation products due to its potential toxicity and investigated fluorescent character. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.06.041

文献信息

• Mechanistic analyses of the suppression of amyloid β42 aggregation by apomorphine
  作者：Mizuho Hanaki、Kazuma Murakami、Sumie Katayama、Ken-ichi Akagi、Kazuhiro Irie

  DOI：10.1016/j.bmc.2018.01.028

  日期：2018.5

  His13,14, Gln15, and Lys16 of the Aβ42 monomer. These regions form intermolecular β-sheets in Aβ42 aggregates. Since 3 did not perturb the chemical shift of monomeric Aβ42, we performed aggregation experiments using 1,1,1,3,3,3-hexafluoro-2-propanol-treated Aβ42 to investigate whether 3 associates with Aβ42 oligomers. Compounds 1 and 3 delayed the onset of the oligomer-driven nucleation phase. Despite their

  （R）-Apomorphine（1）具有减少淀粉样β蛋白（Aβ42）（阿尔茨海默氏病（AD）的病原体）的潜力。尽管将Aβ42聚集抑制为1归因于其酚部分的抗氧化作用，但是其在分子水平上的抑制机理仍有待充分阐明。LC-MS和UV分析显示，在孵育过程中1被自动氧化生成不稳定的邻醌形式（2），该形式与Aβ42的Lys 16和28形成了迈克尔加合物。具有邻醌和菲部分的另一种自氧化形式的1（3）抑制了Aβ42的聚集，可与1媲美，而用还原剂三（2-羧乙基）膦处理1降低了其抑制活性。1H-15N SOFAST-HMQC NMR研究表明1与Aβ42单体的Arg5，His13,14，Gln15和Lys16相互作用。这些区域在Aβ42聚集体中形成分子间β-折叠。由于3不会干扰单体Aβ42的化学位移，因此我们使用1,1,1,3,3,3-六氟-2-丙醇处理过的Aβ42进行了聚集实验，以研究3是否与Aβ42低聚物缔合