6-methoxy-5-nitro-2-quinolinecarboxaldehyde | 1215208-72-2

• 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: 6-methoxy-5-nitro-2-quinolinecarboxaldehyde
• 英文别名: 6-Methoxy-5-nitroquinoline-2-carbaldehyde
• CAS: 1215208-72-2
• 化学式: C₁₁H₈N₂O₄
• 分子量: 232.196
• InChiKey: XJCXNPXDOUOTBX-UHFFFAOYSA-N

物化性质

• 沸点：
  441.8±40.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-methoxy-5-nitro-2-quinolinecarboxaldehyde 、 magnesium,1,2,3-trimethoxybenzene-5-ide,bromide 在 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 生成
  参考文献：
  名称：

  5-Amino-2-Aroylquinolines as Highly Potent Tubulin Polymerization Inhibitors

  摘要：

  A series of aroylquinoline derivatives were synthesized and evaluated for anticancer activity. 5-Amino-6-methoxy-2-aroylquinoline 15 showed more potent antiproliferative activity (IC50 values ranging from 0.2 to 0.4 nM) as compared to 1a (combretastatin A-4) (IC50 = 1.9-835 nM) against various human cancer cell lines and a MDR-resistant cancer cell line. Compound 15 (IC50 = 1.6 mu M) exhibited more potent inhibition of tubulin polymerization than 1a (IC50 = 2.1 mu M) and showed strong binding property to the colchicine binding site of microtubules.

  DOI：

  10.1021/jm900685y
• 作为产物：
  描述：

  6-甲氧基-2-甲基喹啉 在 selenium(IV) oxide 、 硫酸 、 硝酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 51.0h， 生成 6-methoxy-5-nitro-2-quinolinecarboxaldehyde
  参考文献：
  名称：

  AROYLQUINOLINE COMPOUNDS

  摘要：

  提供了一系列含有结构式（I）的硝基杂环衍生物。在结构式（I）中，P、Q和R1至R8在说明书中有定义。本发明揭示的衍生物具有抑制微管聚合的特性，并可使用合适的药用载体治疗癌症和其他与微管聚合有关的疾病。

  公开号：

  US20110275643A1

文献信息

• AROYLQUINOLINE COMPOUNDS
  申请人：Liou Jing-Ping

  公开号：US20110275643A1

  公开（公告）日：2011-11-10

  A serious of nitro heterocyclic derivatives including a structure of formula (I) are provided. In formula (I), P, Q and R1 to R8 are defined in the specification. The derivatives disclosed in the present invention are characterized in inhibiting tubulin polymerization, and treating cancers and other tubulin polymerization-related disorders with a suitable pharmaceutical acceptable carrier.

  提供了一系列含有结构式（I）的硝基杂环衍生物。在结构式（I）中，P、Q和R1至R8在说明书中有定义。本发明揭示的衍生物具有抑制微管聚合的特性，并可使用合适的药用载体治疗癌症和其他与微管聚合有关的疾病。
• 5-Amino-2-Aroylquinolines as Highly Potent Tubulin Polymerization Inhibitors
  作者：Chih-Ying Nien、Yun-Ching Chen、Ching-Chuan Kuo、Hsing-Pang Hsieh、Chi-Yen Chang、Jian-Sung Wu、Su-Ying Wu、Jing-Ping Liou、Jang-Yang Chang

  DOI：10.1021/jm900685y

  日期：2010.3.11

  A series of aroylquinoline derivatives were synthesized and evaluated for anticancer activity. 5-Amino-6-methoxy-2-aroylquinoline 15 showed more potent antiproliferative activity (IC50 values ranging from 0.2 to 0.4 nM) as compared to 1a (combretastatin A-4) (IC50 = 1.9-835 nM) against various human cancer cell lines and a MDR-resistant cancer cell line. Compound 15 (IC50 = 1.6 mu M) exhibited more potent inhibition of tubulin polymerization than 1a (IC50 = 2.1 mu M) and showed strong binding property to the colchicine binding site of microtubules.