7-hydroxy-4-methoxymethyl-6-methylquinolin-2(1H)-one | 406169-90-2

• 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
• 英文名称: 7-hydroxy-4-methoxymethyl-6-methylquinolin-2(1H)-one
• 英文别名: 7-hydroxy-4-methoxymethyl-6-methylquinolin-2-one；2(1H)-Quinolinone, 7-hydroxy-4-(methoxymethyl)-6-methyl-；7-hydroxy-4-(methoxymethyl)-6-methyl-1H-quinolin-2-one
• CAS: 406169-90-2
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: JCKZAYWKDMRASP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-hydroxy-4-methoxymethyl-6-methylquinolin-2(1H)-one 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 72.0h， 生成 4-methoxymethyl-1,6-dimethyl-7-propargyloxyquinolin-2(1H)-one
  参考文献：
  名称：

  4-Hydroxymethyl-1,6,8-trimethylfuro[2,3-h]quinolin-2(1H)-one Induces Mitochondrial Dysfunction and Apoptosis upon Its Intracellular Oxidation

  摘要：

  We investigated the mechanism of cell death induced by a furoquinolinone derivative, namely, 4-hydroxymethyl-1,6,8-trimethylfuro[2,3-h]quinolin-2(1H)-one (HOFQ), in the dark. Mitochondrial depolarization was found to be a causative event in HOFQ-induced apoptosis that was blunted either by replacing the 4-hydroxymethyl group with a methyl one, or by 4-methylpyrazole, an inhibitor of alcohol dehydrogenase (ADH). In vitro enzymatic assay demonstrated that HOFQ is a substrate of ADH. In isolated mitochondria HOFQ was without effect, whereas in the presence of ADH and NAD+ it caused the opening of the permeability transition pore, indicating that HOFQ-oxidized products affect mitochondrial function directly. Finally, an analogue bearing the formyl group at the C-4 position mimicked all the effects exerted by HOFQ In conclusion, these results suggest that the direct action on mitochondria of HOFQ-oxidized products are responsible for their cytotoxicity, which might be exacerbated, but hardly determined, by photodynamic action and/or binding to DNA.

  DOI：

  10.1021/jm0493919
• 作为产物：
  描述：

  2,4-二氨基甲苯 在 硫酸 、 水 、 sodium nitrite 作用下， 反应 24.0h， 生成 7-hydroxy-4-methoxymethyl-6-methylquinolin-2(1H)-one
  参考文献：
  名称：

  新型呋喃[2,3-h]喹啉-2（1H）-one的合成及生物学评价。

  摘要：

  合成了一种新的呋喃喹啉酮衍生物，即4-羟甲基-1,6,8-三甲基呋喃[2,3-h]喹啉-2（1H）-one（HOFQ），并对其生物学活性进行了研究。通过UVA激活，HOFQ在Ehrlich腹水细胞中诱导了强大的抗增殖作用，使其失去了通过移植传播肿瘤的能力。HOFQ表现出较差的遗传毒性和皮肤光毒性。实际上，HOFQ敏化形成DNA-蛋白质交联，但不形成链间交联。因此，HOFQ似乎是用于PUVA光化学疗法和光采的新药。

  DOI：

  10.1021/jm010993r