casticin diacetate | 76215-22-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: casticin diacetate
• 英文别名: casticine acetate；Diacetyl-vitexicarpin；Casticin-diacetat；3,6,7,4'-Tetramethoxy-5,3'-diacetoxy-flavon；[5-(5-Acetyloxy-3,6,7-trimethoxy-4-oxochromen-2-yl)-2-methoxyphenyl] acetate
• CAS: 76215-22-0
• 化学式: C₂₃H₂₂O₁₀
• 分子量: 458.422
• InChiKey: QPRSKSMMRGABTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  蔓荆子黄素 、 乙酸酐 在 高氯酸 作用下， 反应 0.5h， 生成 casticin diacetate
  参考文献：
  名称：

  Antitumor plants. 11. Diterpenoid and flavonoid constituents of Bromelia pinguin L

  摘要：

  DOI：

  10.1021/jo00319a011

文献信息

• Cytotoxic Flavone Analogues of Vitexicarpin, a Constituent of the Leaves of <i>Vitex negundo</i>
  作者：Fredyc Díaz、Daniel Chávez、Dongho Lee、Qiuwen Mi、Hee-Byung Chai、Ghee T. Tan、Leonardus B. S. Kardono、Soedarsono Riswan、Craig R. Fairchild、Robert Wild、Norman R. Farnsworth、Geoffrey A. Cordell、John M. Pezzuto、A. Douglas Kinghorn

  DOI：10.1021/np0300784

  日期：2003.6.1

  Bioassay-guided fractionation of the chloroform-soluble extract of the leaves of Vitex negundo led to the isolation of the known flavone vitexicarpin (1), which exhibited broad cytotoxicity in a human cancer cell line panel. In an attempt to increase the cytotoxic potency of 1, a series of acylation reactions was performed on this compound to obtain its methylated (2), acetylated (3), and six new acylated (4-9) derivatives. Compound 9, the previously unreported 5,3'-dihexanoyloxy-3,6,7,4'-tetramethoxyflavone, showed comparative cytotoxic potency to compound 1 and was selected for further evaluation. However, this compound was found to be inactive when evaluated in the in vivo hollow fiber assay with Lu1, KB, and LNCaP cells at the highest dose (40 mg/kg/body weight) tested, and in the in vivo P-388 leukemia model (135 mg/kg), using the ip administration route.