11-(carboxymethylamino)-5-methylbenzofuro[3,2-b]-quinolin-5-ium iodide | 1384105-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 11-(carboxymethylamino)-5-methylbenzofuro[3,2-b]-quinolin-5-ium iodide
• CAS: 1384105-21-8
• 化学式: C₁₈H₁₅N₂O₃*I
• 分子量: 434.233
• InChiKey: ONKLNWZJKKUIIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.06
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.35
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Fmoc-甘氨酸 、 11-(carboxymethylamino)-5-methylbenzofuro[3,2-b]-quinolin-5-ium iodide 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以29%的产率得到11-(2-(2-(2-amino-2-oxoethylamino)-2-oxoethylamino)-2-oxoethylamino)-5-methylbenzofuro[3,2-b]-quinolin-5-ium iodide
  参考文献：
  名称：

  Benzofuroquinoline Derivatives Had Remarkable Improvement of their Selectivity for Telomeric G-Quadruplex DNA over Duplex DNA upon Introduction of Peptidyl Group

  摘要：

  In order to improve the selectivity of 5-N-methyl quindoline (cryptolepine) derivatives as telomeric quadruplex binding ligands versus duplex DNA, a series of peptidyl-benzofuroquinoline (P-BFQ) conjugates (2a-2n) were designed and synthesized. Their interactions with telomeric quadruplex and duplex DNA were examined by using the fluorescence resonance energy transfer (FRET) melting assay, surface plasmon resonance (SPR), circular dichroism spectroscopy (CD), and molecular modeling studies. Introduction of a peptidyl group at 11-position of the aromatic benzofuroquinoline scaffold not only effectively increased its binding affinity, but also significantly improved its selectivity toward telomeric quadruplex versus duplex DNA. Combined with the data for their inhibitory effects on telomerase activity, their structure-activity relationships (SARs) studies showed that the types of amino acid residues and the length of the peptidyl side chains were important for the improvement of their interactions with the telomeric G-quadruplex. Long-term exposure of human cancer cells to 2c showed a remarkable cessation in population growth and cellular senescence phenotype, and accompanied by a shortening of the telomere length.

  DOI：

  10.1021/bc300123m
• 作为产物：
  描述：

  11-iodo-5-N-methyl-benzofuro[3,2-b]quinolinium iodide 、 聚甘氨酸 以 乙二醇乙醚 为溶剂， 反应 12.0h， 以41%的产率得到11-(carboxymethylamino)-5-methylbenzofuro[3,2-b]-quinolin-5-ium iodide
  参考文献：
  名称：

  Benzofuroquinoline Derivatives Had Remarkable Improvement of their Selectivity for Telomeric G-Quadruplex DNA over Duplex DNA upon Introduction of Peptidyl Group

  摘要：

  In order to improve the selectivity of 5-N-methyl quindoline (cryptolepine) derivatives as telomeric quadruplex binding ligands versus duplex DNA, a series of peptidyl-benzofuroquinoline (P-BFQ) conjugates (2a-2n) were designed and synthesized. Their interactions with telomeric quadruplex and duplex DNA were examined by using the fluorescence resonance energy transfer (FRET) melting assay, surface plasmon resonance (SPR), circular dichroism spectroscopy (CD), and molecular modeling studies. Introduction of a peptidyl group at 11-position of the aromatic benzofuroquinoline scaffold not only effectively increased its binding affinity, but also significantly improved its selectivity toward telomeric quadruplex versus duplex DNA. Combined with the data for their inhibitory effects on telomerase activity, their structure-activity relationships (SARs) studies showed that the types of amino acid residues and the length of the peptidyl side chains were important for the improvement of their interactions with the telomeric G-quadruplex. Long-term exposure of human cancer cells to 2c showed a remarkable cessation in population growth and cellular senescence phenotype, and accompanied by a shortening of the telomere length.

  DOI：

  10.1021/bc300123m