2-(4-Methoxyphenyl)-juglon | 28785-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-Methoxyphenyl)-juglon
• 英文别名: 5-Hydroxy-2-(4-methoxyphenyl)-1,4-naphthochinon；5-hydroxy-2-(4-methoxyphenyl)naphthalene-1,4-dione；5-hydroxy-2-(4-methoxyphenyl)-1,4-naphthoquinone；5-hydroxy-2-(p-methoxyphenyl)-1,4-naphthoquinone
• CAS: 28785-83-3
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: GCSFSXCRGTUQLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-Acetoxy-3-chlor-1,4-naphthochinon 在 tetrafluoroboric acid 、 三氯化铝 、 三正丁基氢锡 、 sodium acetate 、 copper dichloride 作用下， 反应 17.0h， 生成 2-(4-Methoxyphenyl)-juglon
  参考文献：
  名称：

  Wurm; Gurka, Pharmazie, 1997, vol. 52, # 10, p. 739 - 743

  摘要：

  DOI：

文献信息

• [EN] 5-HYDROXY-1,4-NAPHTHALENEDIONE FOR USE IN THE TREATMENT OF CANCER<br/>[FR] 5-HYDROXY-1,4-NAPHTALENEDIONE DESTINÉE À ÊTRE UTILISÉE DANS LE TRAITEMENT DU CANCER
  申请人：GODAVARI BIOREFINERIES LTD

  公开号：WO2022091123A1

  公开（公告）日：2022-05-05

  The present invention discloses compounds for inhibition of uncontrolled cell proliferation particularly cancer stem cells. Particularly, the invention relates to compounds of Formula (I) to (IV) for the treatment of cancer.

  本发明揭示了抑制不受控制的细胞增殖特别是癌症干细胞的化合物。特别地，本发明涉及用于治疗癌症的公式(I)至(IV)的化合物。
• Arylation of Benzo-Fused 1,4-Quinones by the Addition of Boronic Acids under Dicationic Pd(II)-Catalysis
  作者：María Teresa Molina、Cristina Navarro、Ana Moreno、Aurelio G. Csákÿ

  DOI：10.1021/ol902084g

  日期：2009.11.5

  The first examples of the direct arylation of benzo-fused 1,4-quinones by the dicationic Pd(II)-catalyzed addition of arylboronic acids are reported. The addition reaction is carried out under very mild conditions (dioxane-H2O, rt, open air atmosphere) and is tolerant of free OH groups. In addition, the reaction shows high regioselectivity, when using nonsymmetrical quinones as starting materials.
• In vitro antiamyloidogenic properties of 1,4-naphthoquinones
  作者：Paloma Bermejo-Bescós、Sagrario Martín-Aragón、Karim L. Jiménez-Aliaga、Andrea Ortega、María Teresa Molina、Eduardo Buxaderas、Guillermo Orellana、Aurelio G. Csákÿ

  DOI：10.1016/j.bbrc.2010.08.038

  日期：2010.9

  The aim of this study is to find out whether several 1,4-naphthoquinones (1,4-NQ) can interact with the amyloidogenic pathway of the amyloid precursor protein processing, particularly targeting at beta-secretase (BACE), as well as at beta-amyloid peptide (A beta) aggregation and disaggregating preformed A beta fibrils. Compounds bearing hydroxyl groups at the quinoid (2) or benzenoid rings (5,6) as well as some 2- and 3-aryl derivatives (11-15) showed BACE inhibitory activity, without effect on amyloid aggregation or disaggregation. The halogenated compounds 8 and 10 were selective for the inhibition of amyloid aggregation. On the other hand, 1,4-naphthoquinone (1), 6-hydroxy-1,4-naphthoquinone (4) and 2-(3,4-dichlorophenyl)-1,4-naphthoquinone (26) did not show any BACE inhibitory activity but were active on amyloid aggregation and disaggregation preformed A beta fibrils. Juglone (5-hydroxy-1,4-naphthoquinone (3), and 3-(p-hydroxyphenyl)-5-methoxy-1,4-napththoquinone (19) were active on all the three targets. Therefore, we suggest that 1,4-NQ derivatives, specially 3 and 19, should be explored as possible drug candidates or lead compounds for the development of drugs to prevent amyloid aggregation and neurotoxicity in Alzheimer's disease. (C) 2010 Elsevier Inc. All rights reserved.