2-(1-piperidinyl)-4H-1-benzopyran-4-one | 64965-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(1-piperidinyl)-4H-1-benzopyran-4-one
• 英文别名: 2-(piperidin-1-yl)-4H-chromen-4-one；2-piperidin-1-yl-chromen-4-one；Piperidinochromone；2-piperidin-1-ylchromen-4-one
• CAS: 64965-02-2
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: CJVUITXBXBFMJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 4-羟基香豆素 、 2-(1-piperidinyl)-4H-1-benzopyran-4-one 生成 4-hydroxy-3-(4-oxo-2-piperidin-1-yl-4H-chromen-3-ylmethyl)-chromen-2-one
  参考文献：
  名称：

  MAZZEI M.; ROMA G.; ERMILI A., J. HETEROCYCL. CHEM., 1978, 15 NO 4, 605-608

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-(methoxymethoxy)phenyl)-3,3-bis(methylthio)prop-2-en-1-one 在 碘 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 2-(1-piperidinyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  碘介导的 2-(甲硫基)-4 H -chromen-4-ones 的合成及其卤化反应研究

  摘要：

  开发了一种有效的碘介导方法，用于通过容易获得的 1-(2-苄氧基-芳基)-3,3-双-甲基硫烷基的分子内环化合成功能化的 2-(甲硫基)-4 H-色烯-4-酮-丙烯酮。合成的 chromen-4-ones 是各种化学反应的关键前体。从机制上讲，我们观察到碘介导的二硫代乙缩醛分子内环化是通过自由基途径进行的。3-Halo-2-(methylthio)-4 H -chromen-4-ones 是通过各种两锅或一锅卤化方法实现的。

  DOI：

  10.1021/acs.joc.1c00788

文献信息

• Syntheses and Evaluation of 2- or 3-(<i>N</i>-Cyclicamino)chromone Derivatives as Monoamine Oxidase Inhibitors
  作者：Koichi Takao、Tsukasa Sakatsume、Hitoshi Kamauchi、Yoshiaki Sugita

  DOI：10.1248/cpb.c20-00579

  日期：2020.11.1

  A series of 2-(N-cyclicamino)chromone derivatives (1a-4c) and 3-(N-cyclicamino)chromone derivatives (5a-8c) were synthesized, and their monoamine oxidase (MAO) A and B inhibitory activities were studied as part of a structure-activity relationship investigation. Compounds 1a-4c showed no remarkable inhibition for MAO-A or MAO-B, whereas compounds 5a-8c (with a few exceptions) showed significant and selective inhibition of MAO-B. Of these compounds, 7c,7-methoxy-3-(4-phenyl-1-piperazinyl)-4H-1-benzopyran-4-one inhibited MAO-B the most potently and selectively, having IC50 of 15 nM and an MAO-B selectivity index of more than 6700; c.f, 50 nM and 2000, respectively, for safinamide. The mode of inhibition of 7c to MAO-B was competitive and reversible. Considering the IC50 values and selectivity indices of the other synthetic compounds, the presence of the methoxy group on the chromone ring (R-2) of 7c seemed to increase MAO-B inhibition. Molecular docking analysis also supports this hypothesis. Our results suggest that 3-(N-cyclicamino)chromones are useful lead compounds for the development of MAO-B inhibitors.
• Kaye, Perry T.; Ramaite, Isaiah D.I., South African Journal of Chemistry, 2003, vol. 56, p. 25 - 29
  作者：Kaye, Perry T.、Ramaite, Isaiah D.I.

  DOI：——

  日期：——
• ERMILI A.; BALBI A.; DI BRACCIO M.; ROMA G., FARMACO ED. SCI., 1977, 32,
  作者：ERMILI A.、 BALBI A.、 DI BRACCIO M.、 ROMA G.

  DOI：——

  日期：——