Mammeisin-acetat | 27127-44-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: Mammeisin-acetat
• 英文别名: 4-Phenyl-5,7-diacetoxy-6-isovaleryl-8-isopentenyl-cumarin；5,7-diacetoxy-6-isovaleryl-8-(3-methyl-but-2-enyl)-4-phenyl-coumarin；5,7-Diacetoxy-6-isovaleryl-8-(3-methyl-but-2-enyl)-4-phenyl-cumarin；[5-Acetoxy-6-(3-methylbutanoyl)-8-(3-methylbut-2-enyl)-2-oxo-4-phenyl-chromen-7-yl] acetate；[5-acetyloxy-6-(3-methylbutanoyl)-8-(3-methylbut-2-enyl)-2-oxo-4-phenylchromen-7-yl] acetate
• CAS: 27127-44-2
• 化学式: C₂₉H₃₀O₇
• 分子量: 490.553
• InChiKey: OVAGITAYMDGGBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-苯基-5,7-二羟基-6-(3-甲基丁酰基)-8-(3-甲基-2-丁烯基)-2H-1-苯并吡喃-2-酮 、 乙酸酐 在 吡啶 作用下， 反应 3.0h， 以17 mg的产率得到Mammeisin-acetat
  参考文献：
  名称：

  Cytotoxic 4-Phenylcoumarins from the Leaves of Marila pluricostata

  摘要：

  Bioassay-guided fractionation of the CH2Cl2 extract of the leaves of Marila pluricostata led to the isolation of 17 naturally occurring 4-phenyleoumarins, three of them, 5-hydroxy-8,8-dimethyl-4-phenyl-9,10-dihydro8H-pyrano-[2,3-f]chromen-2-one (1), 5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-one (2), and 5,7-dihydroxy-8-(3-methylbut-2-enyl)-4-phenylchromen-2-one (3), are new natural compounds; the remaining (4-17) are known mammea-type coumarins. Their structures were established by spectroscopic means. All compounds were tested in cytotoxicity assays against the MCF-7, H-460, and SF-268 human cancer cell lines.

  DOI：

  10.1021/np049642g

文献信息

• Naturally Occurring Oxygen Heterocyclics. X.¹ 4-Phenyl-5,7-dihydroxy-6-isovaleryl-8-isopentenylcoumarin^2,3
  作者：R. A. FINNEGAN、M. P. MORRIS、CARL DJERASSI

  DOI：10.1021/jo01063a050

  日期：1961.4
• Cytotoxic 4-Phenylcoumarins from the Leaves of <i>Marila </i><i>p</i><i>luricostata</i>
  作者：José L. López-Pérez、Dionisio A. Olmedo、Esther del Olmo、Yelkaira Vásquez、Pablo N. Solís、Mahabir P. Gupta、Arturo San Feliciano

  DOI：10.1021/np049642g

  日期：2005.3.1

  Bioassay-guided fractionation of the CH2Cl2 extract of the leaves of Marila pluricostata led to the isolation of 17 naturally occurring 4-phenyleoumarins, three of them, 5-hydroxy-8,8-dimethyl-4-phenyl-9,10-dihydro8H-pyrano-[2,3-f]chromen-2-one (1), 5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-one (2), and 5,7-dihydroxy-8-(3-methylbut-2-enyl)-4-phenylchromen-2-one (3), are new natural compounds; the remaining (4-17) are known mammea-type coumarins. Their structures were established by spectroscopic means. All compounds were tested in cytotoxicity assays against the MCF-7, H-460, and SF-268 human cancer cell lines.