1-benzyloxy-6-methoxy-naphthalene-2-carbaldehyde | 1093167-44-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-benzyloxy-6-methoxy-naphthalene-2-carbaldehyde
• 英文别名: 6-Methoxy-1-phenylmethoxynaphthalene-2-carbaldehyde
• CAS: 1093167-44-2
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: HUTSJEGRENZXLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-6-methoxy-naphthalene-2-carbaldehyde 、 1-溴-3,4,5-三甲氧基苯 在 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 2-Amino-1-aroylnaphthalene and 2-Hydroxy-1-aroylnaphthalenes as Potent Antitubulin Agents

  摘要：

  A series of aroylnaphthalene derivatives were prepared as bioisosteres of combrestatin A-4 and evaluated for anticancer activity. 2-Amino-1-aroylnaphthalene and 2-hydroxy-1-aroylnaphthalene, 9 and 8, respectively, showed strong antiproliferative activity with IC50 values of 2.1-26.3 nM against a panel of human cancer cell lines including multiple-drug resistant cell line. Compound 9 demonstrated better antiproliferative activity and has a comparable tubulin binding efficacy as that of colchicine.

  DOI：

  10.1021/jm8008635
• 作为产物：
  描述：

  溴甲苯 、 1-羟基-6-甲氧基-萘-2-甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以62%的产率得到1-benzyloxy-6-methoxy-naphthalene-2-carbaldehyde
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 2-Amino-1-aroylnaphthalene and 2-Hydroxy-1-aroylnaphthalenes as Potent Antitubulin Agents

  摘要：

  A series of aroylnaphthalene derivatives were prepared as bioisosteres of combrestatin A-4 and evaluated for anticancer activity. 2-Amino-1-aroylnaphthalene and 2-hydroxy-1-aroylnaphthalene, 9 and 8, respectively, showed strong antiproliferative activity with IC50 values of 2.1-26.3 nM against a panel of human cancer cell lines including multiple-drug resistant cell line. Compound 9 demonstrated better antiproliferative activity and has a comparable tubulin binding efficacy as that of colchicine.

  DOI：

  10.1021/jm8008635

文献信息

• Synthesis and Structure−Activity Relationships of 2-Amino-1-aroylnaphthalene and 2-Hydroxy-1-aroylnaphthalenes as Potent Antitubulin Agents
  作者：Gadarla Randheer Reddy、Ching-Chuan Kuo、Uan-Kang Tan、Mohane Selvaraj Coumar、Chi-Yen Chang、Yi-Kun Chiang、Mei-Jung Lai、Jiann-Yih Yeh、Su-Ying Wu、Jang-Yang Chang、Jing-Ping Liou、Hsing-Pang Hsieh

  DOI：10.1021/jm8008635

  日期：2008.12.25

  A series of aroylnaphthalene derivatives were prepared as bioisosteres of combrestatin A-4 and evaluated for anticancer activity. 2-Amino-1-aroylnaphthalene and 2-hydroxy-1-aroylnaphthalene, 9 and 8, respectively, showed strong antiproliferative activity with IC50 values of 2.1-26.3 nM against a panel of human cancer cell lines including multiple-drug resistant cell line. Compound 9 demonstrated better antiproliferative activity and has a comparable tubulin binding efficacy as that of colchicine.