4-(3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)butan-2-one | 223801-42-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)butan-2-one
• 英文别名: 4-[3-methoxy-4-(oxan-2-yloxy)phenyl]butan-2-one；4-[3-Methoxy-4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]-2-butanone
• CAS: 223801-42-1
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: XYDOIKWKTCWOCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)butan-2-one 在 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.0h， 生成 [6]-shogaol
  参考文献：
  名称：

  Side-chain length is important for shogaols in protecting neuronal cells from β-amyloid insult

  摘要：

  Ten shogaols were synthesized to evaluate the importance of the side-chain length in protecting cells from betaA(1-42) insult using PC12 rat pheochromocytoma and IMR-32 human neuroblastoma cells. The compounds cell protectivity against betaA insult was demonstrated using 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) reduction assay. The efficacy of cell protection from betaA insult by these shogaols was shown to improve as the length of the side chain increase. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.041
• 作为产物：
  描述：

  4-hydroxy-4-(4-hydroxy-3-methoxyphenyl)butan-2-one 在 palladium on activated charcoal 盐酸 、 氢气 、 4-甲基苯磺酸吡啶 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4-(3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)butan-2-one
  参考文献：
  名称：

  Side-chain length is important for shogaols in protecting neuronal cells from β-amyloid insult

  摘要：

  Ten shogaols were synthesized to evaluate the importance of the side-chain length in protecting cells from betaA(1-42) insult using PC12 rat pheochromocytoma and IMR-32 human neuroblastoma cells. The compounds cell protectivity against betaA insult was demonstrated using 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) reduction assay. The efficacy of cell protection from betaA insult by these shogaols was shown to improve as the length of the side chain increase. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.041

文献信息

• Pharmaceutical compositions useful in prevention and treatment of beta-Amyloid protein-induced disease
  申请人：Kim Darrick S. H. L.

  公开号：US06887898B1

  公开（公告）日：2005-05-03

  The invention provides methods for treating beta-Amyloid protein-induced disease, pharmaceutical compositions and compounds useful for the same, and the use of these compounds for the manufacture of a medicament for treating the same. More particularly, the invention relates to the use of natural product compounds isolated from turmeric, gingko biloba, and ginger, and synthetic chemical analogues thereof, for the treatment of a beta-Amyloid protein-induced disease.

  这项发明提供了用于治疗β-淀粉样蛋白诱导疾病的方法，以及用于相同目的的药物组合物和化合物，以及利用这些化合物制造治疗该疾病的药物的用途。更具体地说，该发明涉及利用从姜黄、银杏和姜中分离的天然产物化合物以及其合成化学类似物，用于治疗β-淀粉样蛋白诱导的疾病。
• Combined treatment with zingerone and its novel derivative synergistically inhibits TGF-β1 induced epithelial-mesenchymal transition, migration and invasion of human hepatocellular carcinoma cells
  作者：Young-Joo Kim、Youngsic Jeon、Taejung Kim、Won-Chul Lim、Jungyeob Ham、Young Nyun Park、Tae-Jin Kim、Hyeonseok Ko

  DOI：10.1016/j.bmcl.2016.12.042

  日期：2017.2

  The epithelial-mesenchymal transition (EMT) is an important cellular process during which polarized epithelial cells become motile mesenchymal cells, which promote cancer metastasis. Ginger, the rhizome of Zingiber officinale, is extensively used in cooking worldwide and also as a traditional medicinal herb with antioxidant, anti-inflammatory and anticancer properties. Several pungent compounds have been identified in ginger, including zingerone, which has anticancer potential. However, the role of zingerone in EMT is unclear. We investigated the synergistic effect of zingerone and its derivative on EMT. Transforming growth factor-beta 1 (TGF-beta 1) induces the EMT to promote hepatocellular carcinoma metastasis, including migration and invasion. To understand the repressive role of the combination of zingerone and its derivative (ZD 2) in hepatocellular carcinoma metastasis, we investigated the potential use of each compound of ginger, such as zingerone, ZD 2 and 6-shogaol, or the mixture of zingerone and ZD 2 (ZD 2-1) as inhibitors of TGF-beta 1 induced EMT development in SNU182 hepatocellular carcinoma cells in vitro. We show that ZD 2-1, but not zingerone, ZD 2 and 6-shogaol significantly increased expression of the epithelial marker E-cadherin and repressed Snail upregulation and expression of the mesenchymal marker N-cadherin during initiation of the TGF-beta 1 induced EMT. In addition, ZD 2-1 inhibited the TGF-beta 1 induced increase in cell migration and invasion of SNU182 hepatocellular carcinoma cells. Furthermore, ZD 2-1 significantly inhibited TGF-beta 1 regulated matrix metalloproteinase-2/9 and activation of Smad2/3. We also found that ZD 2-1 inhibited nuclear translocation of NF-kappa B, activation of p42/44 MAPK/AP1 signaling pathway in the TGF-beta 1 induced EMT. Our findings provide new evidence that combined treatment with ZD 2, novel zingerone derivative, and zingerone synergistically suppresses hepatocellular carcinoma metastasis in vitro by inhibiting the TGF-beta 1 induced EMT. (C) 2016 Elsevier Ltd. All rights reserved.
• Synergistic pharmaceutical compositions useful in prevention and treatment of beta-amyloid protein-induced disease
  申请人：Kim S. H. L. Darrick

  公开号：US20070003641A1

  公开（公告）日：2007-01-04

  Disclosed are combinations of natural and synthetic turmeric, ginger, ginko biloba, sage, and rosemary compounds suitable for treatment of beta-amyloid-disease induced disease that have synergistic anti-βA peptide effects when members of the five groups of compounds are combined. Suitable members of the compounds include both natural compounds derived from extracts of each of Curcuma sp., Zingiber sp., Ginkgo biloba, Salvia sp., or Rosmarinus sp. as well as synthetic homologues and analogues of such natural compounds. Sage and rosemary derived compounds suitable alone for treatment of beta-amyloid induced disease is also described.
• US7728043B2
  申请人：——

  公开号：US7728043B2

  公开（公告）日：2010-06-01
• WO2023/146771
  申请人：——

  公开号：——

  公开（公告）日：——