3-[4-[4-(Dimethylamino)phenyl]triazol-1-yl]-7-hydroxy-8-methylchromen-2-one | 1238848-17-3

• 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: 3-[4-[4-(Dimethylamino)phenyl]triazol-1-yl]-7-hydroxy-8-methylchromen-2-one
• CAS: 1238848-17-3
• 化学式: C₂₀H₁₈N₄O₃
• 分子量: 362.388
• InChiKey: QSBRXMYPIPYRGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  80.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[4-[4-(Dimethylamino)phenyl]triazol-1-yl]-7-hydroxy-8-methylchromen-2-one 、 (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， 生成
  参考文献：
  名称：

  Click chemistry to probe Hsp90: Synthesis and evaluation of a series of triazole-containing novobiocin analogues

  摘要：

  A series of triazole-containing novobiocin analogues has been designed, synthesized and their inhibitory activity determined. These compounds contain a triazole ring in lieu of the amide moiety present in the natural product. The anti-proliferative effects of these compounds were evaluated against two breast cancer cell lines ( SKBr-3 and MCF-7), and manifested activities similar to their amide-containing counterparts. In addition, Hsp90-dependent client protein degradation was observed via Western blot analyses, supporting a common mode of Hsp90 inhibition for both structural classes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.140
• 作为产物：
  描述：

  3-azido-7-hydroxy-8-methyl-2H-chromen-2-one 、 4-二甲基氨基苯乙炔 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 3-[4-[4-(Dimethylamino)phenyl]triazol-1-yl]-7-hydroxy-8-methylchromen-2-one
  参考文献：
  名称：

  Click chemistry to probe Hsp90: Synthesis and evaluation of a series of triazole-containing novobiocin analogues

  摘要：

  A series of triazole-containing novobiocin analogues has been designed, synthesized and their inhibitory activity determined. These compounds contain a triazole ring in lieu of the amide moiety present in the natural product. The anti-proliferative effects of these compounds were evaluated against two breast cancer cell lines ( SKBr-3 and MCF-7), and manifested activities similar to their amide-containing counterparts. In addition, Hsp90-dependent client protein degradation was observed via Western blot analyses, supporting a common mode of Hsp90 inhibition for both structural classes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.140

文献信息

• Click chemistry to probe Hsp90: Synthesis and evaluation of a series of triazole-containing novobiocin analogues
  作者：Laura B. Peterson、Brian S.J. Blagg

  DOI：10.1016/j.bmcl.2010.04.140

  日期：2010.7

  A series of triazole-containing novobiocin analogues has been designed, synthesized and their inhibitory activity determined. These compounds contain a triazole ring in lieu of the amide moiety present in the natural product. The anti-proliferative effects of these compounds were evaluated against two breast cancer cell lines ( SKBr-3 and MCF-7), and manifested activities similar to their amide-containing counterparts. In addition, Hsp90-dependent client protein degradation was observed via Western blot analyses, supporting a common mode of Hsp90 inhibition for both structural classes. (C) 2010 Elsevier Ltd. All rights reserved.