N-(6-hydroxynaphthalen-2-yl)-4-methoxy-3-(3-methoxyphenyl)benzamide | 1083314-05-9

• 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: N-(6-hydroxynaphthalen-2-yl)-4-methoxy-3-(3-methoxyphenyl)benzamide
• CAS: 1083314-05-9
• 化学式: C₂₅H₂₁NO₄
• 分子量: 399.446
• InChiKey: YHBDNRKRZZIXQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(6-hydroxynaphthalen-2-yl)-4-methoxy-3-(3-methoxyphenyl)benzamide 、 (3aR,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl 2,2,2-trichloroacetimidate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 N-[6-[[(3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]naphthalen-2-yl]-4-methoxy-3-(3-methoxyphenyl)benzamide
  参考文献：
  名称：

  The Design, Synthesis, and Evaluation of Coumarin Ring Derivatives of the Novobiocin Scaffold that Exhibit Antiproliferative Activity

  摘要：

  Novobiocin, a known DNA gyrase inhibitor, binds to a nucleotide-binding site located on the Hsp90 C-terminus and induces degradation of Hsp90-dependent client proteins at similar to 700 mu M in breast cancer cells (SKBr3). Although many analogues of novobiocin have been synthesized, it was only recently demonstrated that monomeric species exhibit antiproliferative activity against various cancer cell lines. To further refine the essential elements of the coumarin core, a series of modified coumarin derivatives was, synthesized and evaluated to elucidate structure-activity relationships for novobiocin as an anticancer agent. Results obtained from these studies have produced novobiocin analogues that manifest low micromolar activity against several cancer cell lines.

  DOI：

  10.1021/jo801312r
• 作为产物：
  描述：

  N-(4-methoxybenzyl)-N-[6-(benzyloxy)naphthalen-2-yl]-4-methoxy-3-(3-methoxyphenyl)benzamide 在 三氟甲磺酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(6-hydroxynaphthalen-2-yl)-4-methoxy-3-(3-methoxyphenyl)benzamide
  参考文献：
  名称：

  The Design, Synthesis, and Evaluation of Coumarin Ring Derivatives of the Novobiocin Scaffold that Exhibit Antiproliferative Activity

  摘要：

  Novobiocin, a known DNA gyrase inhibitor, binds to a nucleotide-binding site located on the Hsp90 C-terminus and induces degradation of Hsp90-dependent client proteins at similar to 700 mu M in breast cancer cells (SKBr3). Although many analogues of novobiocin have been synthesized, it was only recently demonstrated that monomeric species exhibit antiproliferative activity against various cancer cell lines. To further refine the essential elements of the coumarin core, a series of modified coumarin derivatives was, synthesized and evaluated to elucidate structure-activity relationships for novobiocin as an anticancer agent. Results obtained from these studies have produced novobiocin analogues that manifest low micromolar activity against several cancer cell lines.

  DOI：

  10.1021/jo801312r

文献信息

• The Design, Synthesis, and Evaluation of Coumarin Ring Derivatives of the Novobiocin Scaffold that Exhibit Antiproliferative Activity
  作者：Alison C. Donnelly、Jared R. Mays、Joseph A. Burlison、John T. Nelson、George Vielhauer、Jeffrey Holzbeierlein、Brian S. J. Blagg

  DOI：10.1021/jo801312r

  日期：2008.11.21

  Novobiocin, a known DNA gyrase inhibitor, binds to a nucleotide-binding site located on the Hsp90 C-terminus and induces degradation of Hsp90-dependent client proteins at similar to 700 mu M in breast cancer cells (SKBr3). Although many analogues of novobiocin have been synthesized, it was only recently demonstrated that monomeric species exhibit antiproliferative activity against various cancer cell lines. To further refine the essential elements of the coumarin core, a series of modified coumarin derivatives was, synthesized and evaluated to elucidate structure-activity relationships for novobiocin as an anticancer agent. Results obtained from these studies have produced novobiocin analogues that manifest low micromolar activity against several cancer cell lines.