9,9'-Oxybis-neocomantherin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 9,9'-Oxybis-neocomantherin
• 英文别名: 8-hydroxy-9-(8-hydroxy-5,6-dimethoxy-4-oxo-2-propylbenzo[g]chromen-9-yl)oxy-5,6-dimethoxy-2-propylbenzo[g]chromen-4-one
• 化学式: C₃₆H₃₄O₁₁
• 分子量: 642.659
• InChiKey: JBNOXTFOMBSBBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  甲醇 、 9,9'-Oxybis-neocomantherin 在 硫酸 作用下， 反应 5.0h， 以1.5 mg的产率得到9,9'-oxybis(5,6,8-trimethoxy-2-propyl-4H-benzo[g]chromen-4-one)
  参考文献：
  名称：

  Benzochromenones from the Marine Crinoid Comantheria rotula Inhibit Hypoxia-Inducible Factor-1 (HIF-1) in Cell-Based Reporter Assays and Differentially Suppress the Growth of Certain Tumor Cell Lines

  摘要：

  Hypoxia-inducible factor-1 (HIF-1) is a transcription factor that promotes tumor cell adaptation and survival under hypoxic conditions. HIF-1 is currently recognized as an important molecular target for anticancer drug discovery. The National Cancer Institute open repository of marine invertebrates and algae lipid extracts was evaluated using a T47D breast tumor cell-based reporter assay for HIF-1 inhibitory activity. Bioassay-guided fractionation of an active extract from a crinoid Comantheria rotula yielded seven benzo[g]chromen-4-one and benzo[h]chromen-4-one pigments (1-7). The structures of the new benzo[g]chromenone dimer 9,9'-oxybis-neocomantherin (1) and another new natural pigment 5 were deduced from spectroscopic and spectrometric data. The crinoid pigments significantly inhibited both hypoxia-induced andiron chelator-induced HIF-1 luciferase reporter activity in breast and prostate tumor cells. However, inhibition of HIF-1 in the reporter assay did not translate into a significant decrease in the expression of the downstream HIF-1 target, secreted vascular endothelial growth factor (VEGF). Compound I was found to inhibit tumor cell growth in the NCI 60-cell line panel (GI(50) values of 1.6-18.2 mu M), and compound 6 produced a unique pattern of tumor cell growth suppression. Five cell lines from different organs were hypersensitive to 6 (GI(50) values of 0.29-0.62 mu M), and three others were moderately sensitive (GI(50) values of 2.2-5.1 mu M), while the GI(50) values for most other cell lines ranged from 20 to 47 mu M. Crinoid benzo[g]chromenones were also found to scavenge radicals in a modified DPPH assay.

  DOI：

  10.1021/np070224w

文献信息

• Benzochromenones from the Marine Crinoid Comantheria rotula Inhibit Hypoxia-Inducible Factor-1 (HIF-1) in Cell-Based Reporter Assays and Differentially Suppress the Growth of Certain Tumor Cell Lines
  作者：Jingqiu Dai、Yang Liu、Hong Jia、Yu-Dong Zhou、Dale G. Nagle

  DOI：10.1021/np070224w

  日期：2007.9.1

  Hypoxia-inducible factor-1 (HIF-1) is a transcription factor that promotes tumor cell adaptation and survival under hypoxic conditions. HIF-1 is currently recognized as an important molecular target for anticancer drug discovery. The National Cancer Institute open repository of marine invertebrates and algae lipid extracts was evaluated using a T47D breast tumor cell-based reporter assay for HIF-1 inhibitory activity. Bioassay-guided fractionation of an active extract from a crinoid Comantheria rotula yielded seven benzo[g]chromen-4-one and benzo[h]chromen-4-one pigments (1-7). The structures of the new benzo[g]chromenone dimer 9,9'-oxybis-neocomantherin (1) and another new natural pigment 5 were deduced from spectroscopic and spectrometric data. The crinoid pigments significantly inhibited both hypoxia-induced andiron chelator-induced HIF-1 luciferase reporter activity in breast and prostate tumor cells. However, inhibition of HIF-1 in the reporter assay did not translate into a significant decrease in the expression of the downstream HIF-1 target, secreted vascular endothelial growth factor (VEGF). Compound I was found to inhibit tumor cell growth in the NCI 60-cell line panel (GI(50) values of 1.6-18.2 mu M), and compound 6 produced a unique pattern of tumor cell growth suppression. Five cell lines from different organs were hypersensitive to 6 (GI(50) values of 0.29-0.62 mu M), and three others were moderately sensitive (GI(50) values of 2.2-5.1 mu M), while the GI(50) values for most other cell lines ranged from 20 to 47 mu M. Crinoid benzo[g]chromenones were also found to scavenge radicals in a modified DPPH assay.