(E)-5-(benzyloxy)-2-styryl-4H-pyran-4-one | 1443302-58-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-5-(benzyloxy)-2-styryl-4H-pyran-4-one
• 英文别名: 5-benzyloxy-2-styryl-pyran-4-one；2-[(1E)-2-Phenylethenyl]-5-(phenylmethoxy)-4H-pyran-4-one；2-[(E)-2-phenylethenyl]-5-phenylmethoxypyran-4-one
• CAS: 1443302-58-6
• 化学式: C₂₀H₁₆O₃
• 分子量: 304.345
• InChiKey: XGAYGLNZCONQNA-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-(benzyloxy)-2-styryl-4H-pyran-4-one 在 盐酸 、 溶剂黄146 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 48.0h， 生成 (E)-5-hydroxy-2-styryl-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of kojic acid derivatives as secondary binding site probes of d-amino acid oxidase

  摘要：

  A series of kojic acid (5-hydroxy-2-hydroxymethyl-4H-pyran-4-one) derivatives were synthesized and tested for their ability to inhibit D-amino acid oxidase (DAAO). Various substituents were incorporated into kojic acid at its 2-hydroxymethyl group. These analogs serve as useful molecular probes to explore the secondary binding site, which can be exploited in designing more potent DAAO inhibitors. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.062
• 作为产物：
  描述：

  5-(benzyloxy)-2-(bromomethyl)-4H-pyran-4-one 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 36.17h， 生成 (E)-5-(benzyloxy)-2-styryl-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of kojic acid derivatives as secondary binding site probes of d-amino acid oxidase

  摘要：

  A series of kojic acid (5-hydroxy-2-hydroxymethyl-4H-pyran-4-one) derivatives were synthesized and tested for their ability to inhibit D-amino acid oxidase (DAAO). Various substituents were incorporated into kojic acid at its 2-hydroxymethyl group. These analogs serve as useful molecular probes to explore the secondary binding site, which can be exploited in designing more potent DAAO inhibitors. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.062

文献信息

• Synthesis of kojic acid derivatives as secondary binding site probes of d-amino acid oxidase
  作者：Mithun Raje、Niyada Hin、Bridget Duvall、Dana V. Ferraris、James F. Berry、Ajit G. Thomas、Jesse Alt、Camilo Rojas、Barbara S. Slusher、Takashi Tsukamoto

  DOI：10.1016/j.bmcl.2013.04.062

  日期：2013.7

  A series of kojic acid (5-hydroxy-2-hydroxymethyl-4H-pyran-4-one) derivatives were synthesized and tested for their ability to inhibit D-amino acid oxidase (DAAO). Various substituents were incorporated into kojic acid at its 2-hydroxymethyl group. These analogs serve as useful molecular probes to explore the secondary binding site, which can be exploited in designing more potent DAAO inhibitors. (c) 2013 Elsevier Ltd. All rights reserved.
• Resveratrol-maltol hybrids as multi-target-directed agents for Alzheimer’s disease
  作者：Gang Cheng、Ping Xu、Minkui Zhang、Jing Chen、Rong Sheng、Yongmin Ma

  DOI：10.1016/j.bmc.2018.08.011

  日期：2018.12

  The 3-hydroxypyran-4-one moiety (maltol) was incorporated into the structure of resveratrol to achieve a series of resveratrol-maltol hybrids (8a 8k) as novel multi-target-directed ligands (MTDLs). In vitro biological evaluation of the MTDLs revealed these compounds to have a triple function, namely inhibition of self-induced A beta(1-42) aggregation, antioxidation, and metal chelating activity. Among all the evaluated MTDLs, compounds 8i and 8j showed the most promise, demonstrating micromolar IC50 values for A beta(1-42) aggregation inhibition, more potent ABTS(center dot+) scavenging activity than Trolox, and good metal chelating activities.