3-甲基-2-苯基喹啉-5,8-二酮 | 1021355-10-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 3-甲基-2-苯基喹啉-5,8-二酮
• 英文名称: 3-methyl-2-phenylquinoline-5,8-dione
• CAS: 1021355-10-1
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: JIVQHDNQPOADDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  47.03
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  乙烯亚胺 、 3-甲基-2-苯基喹啉-5,8-二酮 以 乙醇 为溶剂， 反应 1.0h， 以170 mg的产率得到6-aziridinyl-3-methyl-2-phenylquinoline-5,8-dione
  参考文献：
  名称：

  Discovery of Quinolinediones Exhibiting a Heat Shock Response and Angiogenesis Inhibition

  摘要：

  A series of substituted quinoline-5,8-diones were synthesized and evaluated as inhibitors of the chaperone protein Hsp90 using two assays: competition for binding to C-terminal ATP-binding site and competition for binding to N-terminal ATP-binding site. In addition, the ability of the compounds to induce the heat shock response was determined using a reporter fibroblast cell line. Of all the compounds assayed, only 6-aziridinyl-2-biphenylquinoline-5,8-dione induced a heat shock response and did so without interacting at the ATP binding sites of Hsp90. COMPARE analysis was carried out on quinoline-5,8-diones active in the National Cancer Institute's 60-cell line screen with the goal of discovering quinoline-5,8-dione structures that interact with other cellular targets (molecular targets) important for cancer chemotherapy. COMPARE analysis led to the discovery of a combretastatin- like quinoline-5,8-dione structure that, in fact, inhibited angiogenesis.

  DOI：

  10.1021/jm7014099
• 作为产物：
  描述：

  5,8-二甲氧基-3-甲基-2-苯基喹啉 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.58h， 生成 3-甲基-2-苯基喹啉-5,8-二酮
  参考文献：
  名称：

  Discovery of Quinolinediones Exhibiting a Heat Shock Response and Angiogenesis Inhibition

  摘要：

  A series of substituted quinoline-5,8-diones were synthesized and evaluated as inhibitors of the chaperone protein Hsp90 using two assays: competition for binding to C-terminal ATP-binding site and competition for binding to N-terminal ATP-binding site. In addition, the ability of the compounds to induce the heat shock response was determined using a reporter fibroblast cell line. Of all the compounds assayed, only 6-aziridinyl-2-biphenylquinoline-5,8-dione induced a heat shock response and did so without interacting at the ATP binding sites of Hsp90. COMPARE analysis was carried out on quinoline-5,8-diones active in the National Cancer Institute's 60-cell line screen with the goal of discovering quinoline-5,8-dione structures that interact with other cellular targets (molecular targets) important for cancer chemotherapy. COMPARE analysis led to the discovery of a combretastatin- like quinoline-5,8-dione structure that, in fact, inhibited angiogenesis.

  DOI：

  10.1021/jm7014099