7-[[(3aR,4S,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]-3-amino-8-methyl-6-propan-2-yloxychromen-2-one | 1083313-11-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-[[(3aR,4S,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]-3-amino-8-methyl-6-propan-2-yloxychromen-2-one
• CAS: 1083313-11-4
• 化学式: C₂₂H₂₇NO₉
• 分子量: 449.458
• InChiKey: LJXHDRVKEKPHNK-JRBPQWBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3',6-dimethoxy-[1,1'-biphenyl]-3-carboxylic acid 、 7-[[(3aR,4S,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]-3-amino-8-methyl-6-propan-2-yloxychromen-2-one 在 吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-[7-[[(3aR,4S,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]-8-methyl-2-oxo-6-propan-2-yloxychromen-3-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：

  benzyl 6-isopropoxy-7-[(3aR,4S,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy]-8-methyl-2-oxo-2H-chromen-3-ylcarbamate 在 10% Pd/C 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 7-[[(3aR,4S,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]-3-amino-8-methyl-6-propan-2-yloxychromen-2-one
  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