3-morpholinochromone | 40302-80-5

• 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: 3-morpholinochromone
• 英文别名: 3-(4-morpholinyl)-4H-1-benzopyran-4-one；3-N-Morpholinochromon；3-Morpholinochromon；3-morpholin-4-yl-chromen-4-one；3-morpholino-4H-chromen-4-one；3-morpholin-4-ylchromen-4-one
• CAS: 40302-80-5
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: DBSFOQMKGXPWOB-UHFFFAOYSA-N

物化性质

• 沸点：
  366.0±42.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-morpholinochromone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以90%的产率得到cis-3-morpholino-chroman-4-ol
  参考文献：
  名称：

  A NEW SYNTHESIS OF CIS-3-SUBSTITUTED CHROMAN-4-OLS

  摘要：

  3,3-Dibromochroman-4-ones on reaction with different heterocyclic secondary amines gave 3-substituted chromones. These on reduction with NaBH4 gave exclusively cis-3-heterocycle substituted chroman-4-ols in good yields.

  DOI：

  10.1081/scc-120005433
• 作为产物：
  描述：

  色酮 在 双氧水 、 苄基三甲基氢氧化铵 作用下， 以 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 4.08h， 生成 3-morpholinochromone
  参考文献：
  名称：

  Syntheses and Evaluation of 2- or 3-(<i>N</i>-Cyclicamino)chromone Derivatives as Monoamine Oxidase Inhibitors

  摘要：

  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.

  DOI：

  10.1248/cpb.c20-00579

文献信息

• Some 3-amino-4-chromanol derivatives
  作者：É. K. Orlova、N. S. Tolmacheva、L. M. Meshcheryakova、V. A. Zagorevskii

  DOI：10.1007/bf00771676

  日期：1973.1