3,4-bis(6'-bromohexyloxy)-9H-xanthen-9-one | 1187388-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3,4-bis(6'-bromohexyloxy)-9H-xanthen-9-one
• 英文别名: 3,4-Bis(6-bromohexoxy)xanthen-9-one
• CAS: 1187388-93-7
• 化学式: C₂₅H₃₀Br₂O₄
• 分子量: 554.319
• InChiKey: XVOXUUCYUHQUIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,6-二溴己烷 、 3,4-二羟基氧杂蒽酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.75h， 以40%的产率得到3-(6'-bromohexyloxy)-4-hydroxy-9H-xanthen-9-one
  参考文献：
  名称：

  Bromoalkoxyxanthones as promising antitumor agents: Synthesis, crystal structure and effect on human tumor cell lines

  摘要：

  In a study involving the synthesis of bis-intercalators, a bisxanthone and a minor product, 1-(6-bromohexyloxy)-xanthone were obtained. Although no capacity to inhibit the growth of human tumor cell lines was observed for the bisxanthone, the bromoalkoxyxanthone revealed this biological activity. In light of these results bromoalkylation of 3,4-dihydroxyxanthone furnished two bromohexyloxyxanthones that were investigated for their effect on the in vitro growth of human tumor cell lines MCF-7 (ER+, breast), MDA-MB-231 (ER-, breast), NCI-H460 (non-small lung), and SF-268 (central nervous system). The X-ray structure of 1-(6-bromohexyloxy)-xanthone revealed that the xanthone skeleton remains essentially planar forming a dihedral angle of 61.3(2)degrees with the 6-bromohexyl side chain. These results revealed bromoalkoxyxanthones as interesting scaffolds to look for potential anticancer drugs. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.04.011

文献信息

• Bromoalkoxyxanthones as promising antitumor agents: Synthesis, crystal structure and effect on human tumor cell lines
  作者：Emília Sousa、Ana Paiva、Nair Nazareth、Luis Gales、Ana M. Damas、Maria S.J. Nascimento、Madalena Pinto

  DOI：10.1016/j.ejmech.2009.04.011

  日期：2009.9

  In a study involving the synthesis of bis-intercalators, a bisxanthone and a minor product, 1-(6-bromohexyloxy)-xanthone were obtained. Although no capacity to inhibit the growth of human tumor cell lines was observed for the bisxanthone, the bromoalkoxyxanthone revealed this biological activity. In light of these results bromoalkylation of 3,4-dihydroxyxanthone furnished two bromohexyloxyxanthones that were investigated for their effect on the in vitro growth of human tumor cell lines MCF-7 (ER+, breast), MDA-MB-231 (ER-, breast), NCI-H460 (non-small lung), and SF-268 (central nervous system). The X-ray structure of 1-(6-bromohexyloxy)-xanthone revealed that the xanthone skeleton remains essentially planar forming a dihedral angle of 61.3(2)degrees with the 6-bromohexyl side chain. These results revealed bromoalkoxyxanthones as interesting scaffolds to look for potential anticancer drugs. (C) 2009 Elsevier Masson SAS. All rights reserved.