3-hydroxy-6-methyl-2-piperidinomethylpyran-4(1H)-one | 1038924-54-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-hydroxy-6-methyl-2-piperidinomethylpyran-4(1H)-one
• 英文别名: 3-hydroxy-6-methyl-2-[(piperidin-1-yl)methyl]-pyran-4(1H)-one；3-hydroxy-6-methyl-2-[(piperidine-1-yl)methyl]-4H-pyran-4-one；3-Hydroxy-6-methyl-2-(1-piperidylmethyl)pyran-4-one；3-hydroxy-6-methyl-2-(piperidin-1-ylmethyl)pyran-4-one
• CAS: 1038924-54-7
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: CUBQYAUDOIVNDG-UHFFFAOYSA-N

物化性质

• 熔点：
  150-151 °C(Solv: methanol (67-56-1))
• 沸点：
  377.5±42.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 3-hydroxy-6-methyl-2-piperidinomethylpyran-4(1H)-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以73%的产率得到chlorido{3-(oxo-κO)-6-methyl-2-[(piperidin-1-yl)methyl]pyran-4(1H)-onato-κO}(η⁶-p-cymene)ruthenium(II)
  参考文献：
  名称：

  Organometallic complexes of (thio)allomaltol-based Mannich-products: Synthesis, stability and preliminary biological investigations

  摘要：

  Organometallic complexes with (thio) pyrone-based ligands have been shown to possess promising cytotoxic properties. To extend the class of potential metallodrugs, the (thio) pyrone backbone was modified via Mannich reaction with morpholine, N-methylpiperazine and piperidine as cyclic amine. The ligands and organometallic complexes were characterized by means of 1D and 2D NMR, ESI MS and also in one case by X-ray diffraction analysis. Due to the high aqueous solubility, the behavior and stability in aqueous solution of the synthesized complexes was studied by 1H NMR spectroscopy. In addition, the influence of these modifications on cytotoxicity in human cancer cell lines was investigated by means of the MTT assay. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.10.044
• 作为产物：
  描述：

  (2-氯甲基)-5-羟基-4H-吡喃-4-酮 在 盐酸 、 锌 作用下， 以 甲醇 、 水 为溶剂， 反应 0.08h， 生成 3-hydroxy-6-methyl-2-piperidinomethylpyran-4(1H)-one
  参考文献：
  名称：

  Organometallic complexes of (thio)allomaltol-based Mannich-products: Synthesis, stability and preliminary biological investigations

  摘要：

  Organometallic complexes with (thio) pyrone-based ligands have been shown to possess promising cytotoxic properties. To extend the class of potential metallodrugs, the (thio) pyrone backbone was modified via Mannich reaction with morpholine, N-methylpiperazine and piperidine as cyclic amine. The ligands and organometallic complexes were characterized by means of 1D and 2D NMR, ESI MS and also in one case by X-ray diffraction analysis. Due to the high aqueous solubility, the behavior and stability in aqueous solution of the synthesized complexes was studied by 1H NMR spectroscopy. In addition, the influence of these modifications on cytotoxicity in human cancer cell lines was investigated by means of the MTT assay. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.10.044

文献信息

• Basic 3-hydroxypyridin-4-ones: Potential antimalarial agents
  作者：Lotfollah S. Dehkordi、Zu D. Liu、Robert C. Hider

  DOI：10.1016/j.ejmech.2007.07.011

  日期：2008.5

  3-Hydroxypyridin-4-ones selectively bind iron under biological conditions and one such compound has found application in the treatment of thalassaemia-linked iron overload. Related molecules have also been demonstrated to possess an antimalarial effect at levels which are non-toxic to mammalian cells. In an attempt to improve the efficiency of such molecules we have investigated the effect of introducing basic nitrogen centres into 3-hydroxypyridin-4-ones in an attempt to achieve targeting to lysosomes and other intracellular acidic vacuoles. Several of the compounds reported in this communication possess enhanced antimalarial activity over that of the simple hydroxypyridinone class. (C) 2007 Elsevier Masson SAS. All rights reserved.