(E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-but-3-enyl ester | 377047-67-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-but-3-enyl ester
• 英文别名: [(E)-4-(4-hydroxy-3-methoxyphenyl)-2-oxobut-3-enyl] (E)-3-(4-acetyloxyphenyl)prop-2-enoate
• CAS: 377047-67-1
• 化学式: C₂₂H₂₀O₇
• 分子量: 396.397
• InChiKey: VAJNFAKVORPLSG-KFXZBRJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-but-3-enyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以22%的产率得到4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3-butenyl 3-(4-hydroxyphenyl)-propenoate
  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：

  3-甲氧基-4-[(四氢-2H-吡喃-2-基)氧基]苯甲醛 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 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 1.0h， 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

文献信息

• Total synthesis of calebin-A, preparation of its analogues, and their neuronal cell protectivity against β-amyloid insult
  作者：Darrick S.H.L Kim、Jin Yung Kim

  DOI：10.1016/s0960-894x(01)00489-9

  日期：2001.9

  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.