12-ethyl-21-hydroxypentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),4,6,8,12,15,17,19-nonaene-3,10,14-trione | 1393489-04-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 12-ethyl-21-hydroxypentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),4,6,8,12,15,17,19-nonaene-3,10,14-trione
• CAS: 1393489-04-7
• 化学式: C₂₃H₁₄O₄
• 分子量: 354.362
• InChiKey: MXYOSGCKAVGYOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  正溴丁烷 、 2-羟基-1,4-萘醌 在 二茂铁 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 41.0h， 以13.2%的产率得到12-ethyl-21-hydroxypentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),4,6,8,12,15,17,19-nonaene-3,10,14-trione
  参考文献：
  名称：

  Unexpected One-Pot Synthesis of Highly Conjugated Pentacyclic Diquinoid Compounds

  摘要：

  A new class of pentacyclic diquinoid compounds has been synthesized with a facile one-pot reaction of two molecules of 2-hydroxynaphthoquinone and 1-bromoalkanes in the presence of ferrocene. These molecules were isolated as enol tautomers that exhibit intramolecular hydrogen bond and extended electronic conjugation as proved by the intense absorption spectrum with a broad band between 400 and 600 nm. The spectroscopic and electrochemical characterization of this new class of compounds has been performed. One of the synthesized diquinoid derivatives showed a significant cytotoxicity with IC50 values of 25-50 mu M against Cisplatin-Resistant SKOV3 and colon carcinoma SW480 cell lines. The results of our study provide a valuable tool to a one-pot synthesis of highly conjugated polyquinones, analogous to important biological systems, with significant antitumoral activity.

  DOI：

  10.1021/jo300985x