N-(7-(((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-8-methyl-2-oxo-2H-chromen-3-yl)benzenesulfonamide | 1016954-19-0

• 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: N-(7-(((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-8-methyl-2-oxo-2H-chromen-3-yl)benzenesulfonamide
• CAS: 1016954-19-0
• 化学式: C₂₅H₂₅NO₁₀S
• 分子量: 531.54
• InChiKey: KAHZYJHLNBHOEA-ZZLPTCMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  139.6
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N-(7-(((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-8-methyl-2-oxo-2H-chromen-3-yl)benzenesulfonamide 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以79%的产率得到N-(7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl)benzenesulfonamide
  参考文献：
  名称：

  Development of Novobiocin Analogues That Manifest Anti-proliferative Activity against Several Cancer Cell Lines

  摘要：

  Recent studies have shown that the DNA gyrase inhibitor, novobiocin, binds to a previously unrecognized ATP-binding site located at the C-terminus of Hsp90 and induces degradation of Hsp90-dependent client proteins at similar to 700 mu M. As a result of these studies, several analogues of the coumarin family of antibiotics have been reported and shown to exhibit increased Hsp90 inhibitory activity; however, the monomeric species lacked the ability to manifest anti-proliferative activity against cancer cell lines at concentrations tested. In an effort to develop more efficacious compounds that produce growth inhibitory activity against cancer cell lines, structure-activity relationships; were investigated surrounding the prenylated benzamide side chain of the natural product. Results obtained from these studies have produced the first novobiocin analogues that manifest anti-proliferative activity against several cancer cell lines.

  DOI：

  10.1021/jo702191a
• 作为产物：
  描述：

  3-amino-7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxooxotetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-8-methyl-2H-chromen-2-one 、 苯磺酰氯 在 吡啶 作用下， 反应 14.0h， 以69%的产率得到N-(7-(((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-8-methyl-2-oxo-2H-chromen-3-yl)benzenesulfonamide
  参考文献：
  名称：

  Development of Novobiocin Analogues That Manifest Anti-proliferative Activity against Several Cancer Cell Lines

  摘要：

  Recent studies have shown that the DNA gyrase inhibitor, novobiocin, binds to a previously unrecognized ATP-binding site located at the C-terminus of Hsp90 and induces degradation of Hsp90-dependent client proteins at similar to 700 mu M. As a result of these studies, several analogues of the coumarin family of antibiotics have been reported and shown to exhibit increased Hsp90 inhibitory activity; however, the monomeric species lacked the ability to manifest anti-proliferative activity against cancer cell lines at concentrations tested. In an effort to develop more efficacious compounds that produce growth inhibitory activity against cancer cell lines, structure-activity relationships; were investigated surrounding the prenylated benzamide side chain of the natural product. Results obtained from these studies have produced the first novobiocin analogues that manifest anti-proliferative activity against several cancer cell lines.

  DOI：

  10.1021/jo702191a