2-hydroxy-6-methoxy-1-(3',4',5'-trimethoxybenzoyl)naphthalene | 1093167-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-6-methoxy-1-(3',4',5'-trimethoxybenzoyl)naphthalene
• 英文别名: (2-Hydroxy-6-methoxynaphthalen-1-yl)-(3,4,5-trimethoxyphenyl)methanone
• CAS: 1093167-26-0
• 化学式: C₂₁H₂₀O₆
• 分子量: 368.386
• InChiKey: YCLJBRKKEVTLPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-hydroxy-6-methoxy-1-(3',4',5'-trimethoxybenzoyl)naphthalene 、 三氟甲烷磺基苯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以51%的产率得到6-methoxy-2-(trifluoromethanesulfonyloxy)-1-(3',4',5'-trimethoxybenzoyl)naphthalene
  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：

  2-benzyloxy-6-methoxy-1-(3',4',5'-trimethoxybenzoyl)naphthalene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以78%的产率得到2-hydroxy-6-methoxy-1-(3',4',5'-trimethoxybenzoyl)naphthalene
  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.