Acetic acid (2S,3R,3aR)-5-allyl-2-(3,4-dimethoxy-phenyl)-3-methyl-6-oxo-2,3-dihydro-6H-benzofuran-3a-yl ester | 104832-99-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: Acetic acid (2S,3R,3aR)-5-allyl-2-(3,4-dimethoxy-phenyl)-3-methyl-6-oxo-2,3-dihydro-6H-benzofuran-3a-yl ester
• 英文别名: [(2S,3R,3aR)-2-(3,4-dimethoxyphenyl)-3-methyl-6-oxo-5-prop-2-enyl-2,3-dihydro-1-benzofuran-3a-yl] acetate
• CAS: 104832-99-7
• 化学式: C₂₂H₂₄O₆
• 分子量: 384.429
• InChiKey: BUJIJNBODIQJAG-BGUDKVOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  海风藤酮 在 溶剂黄146 、 锌 作用下， 以 溶剂黄146 为溶剂， 生成 Acetic acid (2S,3R,3aR)-5-allyl-2-(3,4-dimethoxy-phenyl)-3-methyl-6-oxo-2,3-dihydro-6H-benzofuran-3a-yl ester
  参考文献：
  名称：

  Structure-activity relationships of kadsurenone analogues

  摘要：

  Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol. Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 X 10(-7) M, which is about 50% of the activity of the natural product (IC50 = 1 X 10(-7) M). The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.

  DOI：

  10.1021/jm00384a023

文献信息

• Structure-activity relationships of kadsurenone analogues
  作者：Mitree M. Ponpipom、Robert L. Bugianesi、David R. Brooker、Bao-zhen Yue、San-bao Hwang、Tsung-ying Shen

  DOI：10.1021/jm00384a023

  日期：1987.1

  Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol. Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 X 10(-7) M, which is about 50% of the activity of the natural product (IC50 = 1 X 10(-7) M). The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.