4-Hydroxy-4-[3-methoxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-1-(tetrahydro-pyran-2-yloxy)-butan-2-one | 336784-85-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Hydroxy-4-[3-methoxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-1-(tetrahydro-pyran-2-yloxy)-butan-2-one
• 英文别名: 4-Hydroxy-4-[3-methoxy-4-(oxan-2-yloxy)phenyl]-1-(oxan-2-yloxy)butan-2-one；4-hydroxy-4-[3-methoxy-4-(oxan-2-yloxy)phenyl]-1-(oxan-2-yloxy)butan-2-one
• CAS: 336784-85-1
• 化学式: C₂₁H₃₀O₇
• 分子量: 394.465
• InChiKey: FDDSXGUPWKKQEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-4-[3-methoxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-1-(tetrahydro-pyran-2-yloxy)-butan-2-one 在 4-二甲氨基吡啶 、 4-(dimethylamino)pyridine hydrochloride 、 4-甲基苯磺酸吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-but-3-enyl ester
  参考文献：
  名称：

  Total synthesis of calebin-A, preparation of its analogues, and their neuronal cell protectivity against β-amyloid insult

  摘要：

  A total synthesis of Calebin-A (1), a novel curcuminoid isolated from turmeric (Curcuma longa, Zingiberaceae) that has been demonstrated to protect neuronal cells from beta -amyloid insult, was successfully achieved in four steps. Elaborating on this synthetic route. 13 analogues were prepared for a structure-activity relationship (SAR) study. It was found that the parent compound 1 and derivatives 21, 28, and 30 protect PC12 rat pheocromocytoma and IMR-32 human neuroblastoma cells from beta -amyloid(25-35) insult. These results suggest that hydroxy group at para-position is most critical for the expression of biological activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00489-9
• 作为产物：
  描述：

  1-hydroxypropan-2-one tetrahydropyran ether 、 3-甲氧基-4-[(四氢-2H-吡喃-2-基)氧基]苯甲醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到4-Hydroxy-4-[3-methoxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-1-(tetrahydro-pyran-2-yloxy)-butan-2-one
  参考文献：
  名称：

  Pharmaceutical compositions useful in prevention and treatment of beta-Amyloid protein-induced disease

  摘要：

  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。

  公开号：

  US06887898B1

文献信息

• SYNTHESIS OF CALEBIN-A AND ITS BIOLOGICALLY ACTIVE ANALOGS
  申请人：Majeed Muhammed

  公开号：US20160002141A1

  公开（公告）日：2016-01-07

  Disclosed is a simple, economical, industrially scalable green synthetic process for Calebin-A and its biologically active analogs.

  本发明公开了一种简单、经济、工业可扩展的绿色合成过程，用于合成Calebin-A及其生物活性类似物。
• Synthesis of Calebin-A and its biologically active analogs
  申请人：Majeed, Muhammed

  公开号：EP2963007A1

  公开（公告）日：2016-01-06

  Disclosed is a simple, economical, industrially scalable green synthetic process for Calebin-A and its biologically active analogs.

  所公开的是一种简单、经济、可工业化扩展的 Calebin-A 及其生物活性类似物的绿色合成工艺。
• 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
• US9365486B2
  申请人：——

  公开号：US9365486B2

  公开（公告）日：2016-06-14