1-decyl-3-hydroxy-2-methyl-4(1H)-pyridinone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-decyl-3-hydroxy-2-methyl-4(1H)-pyridinone
• 英文别名: 1-Decyl-3-hydroxy-2-methylpyridin-4-one
• 化学式: C₁₆H₂₇NO₂
• 分子量: 265.396
• InChiKey: IFVJFFVXPHNLLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  麦芽醇 、 1-氨基癸烷 在 盐酸 作用下， 以 水 为溶剂， 反应 168.0h， 以16%的产率得到1-decyl-3-hydroxy-2-methyl-4(1H)-pyridinone
  参考文献：
  名称：

  Oxovanadium complexes with quinoline and pyridinone ligands: Syntheses of the complexes and effect of alkyl chains on their apoptosis-inducing activity in leukemia cells

  摘要：

  Vanadium complexes with quinoline ligands (1b-g) and pyridinone ligands (2b-d) were synthesized, and the effect of the length and shape of alkyl chains on the antiproliferative activity toward U937 cells was studied. For the synthesis of the vanadium complexes, quinoline and pyridinone ligands were prepared and then treated with VOSO4 or VO(acac)(2). The vanadyl(IV) complexes were characterized by IR, ESR, and UV-vis spectroscopy and elemental analyses. The antiproliferative activity of 1a-g toward U937 cells showed little dependence on the length and shape of the alkyl chain. In contrast, a good correlation was found between the IC50 values and partition coefficients (logP) values of 2a-c. Among them, 2c showed the highest inhibitory activity, and its IC50 value was smaller than that of cisplatin. The apoptosis-inducing ability of 2b and 2c was supported by annexin V-propidium iodide staining experiments and agarose gel electrophoresis analysis. Inhibitors of caspase-3, -8, and -9 did not affect the antiproliferative activity of 2c, indicating that the apoptosis induced by 2c was via a caspase-independent pathway. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.063

文献信息

• Oxovanadium complexes with quinoline and pyridinone ligands: Syntheses of the complexes and effect of alkyl chains on their apoptosis-inducing activity in leukemia cells
  作者：Tomoko Yamaguchi、Shinya Watanabe、Yuriko Matsumura、Yoshikazu Tokuoka、Akihiro Yokoyama

  DOI：10.1016/j.bmc.2012.02.063

  日期：2012.5

  Vanadium complexes with quinoline ligands (1b-g) and pyridinone ligands (2b-d) were synthesized, and the effect of the length and shape of alkyl chains on the antiproliferative activity toward U937 cells was studied. For the synthesis of the vanadium complexes, quinoline and pyridinone ligands were prepared and then treated with VOSO4 or VO(acac)(2). The vanadyl(IV) complexes were characterized by IR, ESR, and UV-vis spectroscopy and elemental analyses. The antiproliferative activity of 1a-g toward U937 cells showed little dependence on the length and shape of the alkyl chain. In contrast, a good correlation was found between the IC50 values and partition coefficients (logP) values of 2a-c. Among them, 2c showed the highest inhibitory activity, and its IC50 value was smaller than that of cisplatin. The apoptosis-inducing ability of 2b and 2c was supported by annexin V-propidium iodide staining experiments and agarose gel electrophoresis analysis. Inhibitors of caspase-3, -8, and -9 did not affect the antiproliferative activity of 2c, indicating that the apoptosis induced by 2c was via a caspase-independent pathway. (C) 2012 Elsevier Ltd. All rights reserved.