[4]-shogaol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: [4]-shogaol
• 英文别名: (E)-1-(4-hydroxy-3-methoxyphenyl)oct-4-en-3-one
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: PHHDVGGCTAPBHF-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [4]-shogaol 在 sodium hydrogensulfite 作用下， 以 乙醇 、 水 为溶剂， 反应 0.75h， 以98%的产率得到4-gingesulfonic acid
  参考文献：
  名称：

  首次对映体合成姜磺酸，并确定其绝对立体化学。

  摘要：

  在本文中，我们报道了通过温和且方便的氨基硫脲催化的亚硫酸氢盐向α，β-不饱和羰基的烯烃部分共轭加成，这是我们先前报道的第一个有机催化的对氨基磺酸和Shogas磺酸的对映选择性合成。以其天然和非天然构型制备了一系列光学活性的天然磺酸，并且它们的绝对构型通过单晶X射线衍射法明确证实。

  DOI：

  10.1039/c9ob02662b
• 作为产物：
  描述：

  姜酮 在 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 2.0h， 生成 [4]-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

文献信息

• Shogaol–huprine hybrids: Dual antioxidant and anticholinesterase agents with β-amyloid and tau anti-aggregating properties
  作者：F. Javier Pérez-Areales、Ornella Di Pietro、Alba Espargaró、Anna Vallverdú-Queralt、Carles Galdeano、Ilaria M. Ragusa、Elisabet Viayna、Catherine Guillou、M. Victòria Clos、Belén Pérez、Raimon Sabaté、Rosa M. Lamuela-Raventós、F. Javier Luque、Diego Muñoz-Torrero

  DOI：10.1016/j.bmc.2014.07.053

  日期：2014.10

  Multitarget compounds are increasingly being pursued for the effective treatment of complex diseases. Herein, we describe the design and synthesis of a novel class of shogaol-huprine hybrids, purported to hit several key targets involved in Alzheimer's disease. The hybrids have been tested in vitro for their inhibitory activity against human acetylcholinesterase and butyrylcholinesterase and antioxidant activity (ABTS.+, DPPH and Folin-Ciocalteu assays), and in intact Escherichia coli cells for their Aβ42 and tau anti-aggregating activity. Also, their brain penetration has been assessed (PAMPA-BBB assay). Even though the hybrids are not as potent AChE inhibitors or antioxidant agents as the parent huprine Y and [4]-shogaol, respectively, they still exhibit very potent anticholinesterase and antioxidant activities and are much more potent Aβ42 and tau anti-aggregating agents than the parent compounds. Overall, the shogaol-huprine hybrids emerge as interesting brain permeable multitarget anti-Alzheimer leads.
• Nomura; el Choi, Sci. Rep. Tohoku Univ., Ser. 1: Phys., Chem., Astron., vol. 17, p. 708
  作者：Nomura、el Choi

  DOI：——

  日期：——
• 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.
• Pharmaceutical Compositions Useful In Prevention and Treatment of Beta-Amyloid Protein-Induced Disease
  申请人：Kim S.H.L. Darrick

  公开号：US20080085932A1

  公开（公告）日：2008-04-10

  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.
• Ginger Fraction For Inhibiting Human Cyp Enzymes
  申请人：Ebner Thomas

  公开号：US20080300304A1

  公开（公告）日：2008-12-04

  The present invention relates to a process for preparing a ginger fraction, the fraction prepared by this process and the use thereof on its own or combined with drugs for inhibiting human cytochrome P450 (CYP) enzymes (particularly cytochrome P450 3A4, CYP3A4) for positively influencing the oral bioavailability and pharmacokinetics of active substances.