3-(4-methoxy-phenyl)-7-(2-morpholin-1-yl-ethoxy)-4H-chromen-4-one | 903851-24-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-(4-methoxy-phenyl)-7-(2-morpholin-1-yl-ethoxy)-4H-chromen-4-one
• 英文别名: 3-(4-methoxyphenyl)-7-(2-morpholin-4-ylethoxy)-4H-chromen-4-one；3-(4-methoxyphenyl)-7-(2-morpholinoethoxy)-4H-chromen-4-one；3-(4-Methoxyphenyl)-7-(2-morpholin-4-ylethoxy)chromen-4-one
• CAS: 903851-24-1
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: NRHGDOIQXBULPO-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C
• 沸点：
  570.0±50.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4-methoxy-phenyl)-7-(2-morpholin-1-yl-ethoxy)-4H-chromen-4-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 以84%的产率得到2-[4-(4-methoxyphenyl)-1H-pyrazol-3-yl]-5-(2-morpholin-4-ylethoxy)phenol
  参考文献：
  名称：

  Synthesis of 7-β-(N,N-dialkylamino)ethoxy derivatives of natural isoflavones and 4-aryl-3-[2-hydroxy-4-β-(N,N-dialkylamino) ethoxy]phenylpyrazoles based on them

  摘要：

  合成了福莫西汀、2-甲基福莫西汀和克拉德林的 7-O-β-(N,N-二烷基氨基)乙基衍生物。研究了它们在水合肼作用下的再循环。获得了一系列 4-芳基-3-[2-羟基-4-β-(N,N-二烷基氨基)乙氧基]苯基吡唑。

  DOI：

  10.1007/s10600-013-0500-9
• 作为产物：
  描述：

  刺芒柄花素 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(4-methoxy-phenyl)-7-(2-morpholin-1-yl-ethoxy)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis of 7-β-(N,N-dialkylamino)ethoxy derivatives of natural isoflavones and 4-aryl-3-[2-hydroxy-4-β-(N,N-dialkylamino) ethoxy]phenylpyrazoles based on them

  摘要：

  合成了福莫西汀、2-甲基福莫西汀和克拉德林的 7-O-β-(N,N-二烷基氨基)乙基衍生物。研究了它们在水合肼作用下的再循环。获得了一系列 4-芳基-3-[2-羟基-4-β-(N,N-二烷基氨基)乙氧基]苯基吡唑。

  DOI：

  10.1007/s10600-013-0500-9

文献信息

• Design, synthesis, biological evaluation, and molecular docking of novel flavones as H₃R inhibitors
  作者：Gang Wen、Qian Liu、Huabin Hu、Dongmei Wang、Song Wu

  DOI：10.1111/cbdd.12981

  日期：2017.10

  A series of novel flavone derivatives were designed, synthesized, and evaluated for their H3R inhibitory activity. The results showed that four compounds exhibited significant anti-H3R activity. Molecular docking experiments indicated that a salt bridge, hydrogen-bonding, and hydrophobic interactions all contributed to interactions between inhibitors and H3R.

  设计，合成和评估了一系列新颖的黄酮衍生物的H 3 R抑制活性。结果显示四种化合物显示出显着的抗H 3 R活性。分子对接实验表明，盐桥，氢键和疏水相互作用都促进了抑制剂与H 3 R之间的相互作用。
• Synthetic analogs of daidzein, having more potent osteoblast stimulating effect
  作者：Dinesh K. Yadav、Abnish K. Gautam、Jyoti Kureel、Kamini Srivastava、Mahendra Sahai、Divya Singh、Naibedya Chattopadhyay、Rakesh Maurya

  DOI：10.1016/j.bmcl.2010.12.008

  日期：2011.1

  A series of didzein derivatives were synthesized and assessed for stimulation of osteoblast differentiation using primary cultures of rat calvarial osteoblasts. Data suggested that three synthetic analogs, 1c, 3a and 3c were several folds more potent than daidzein in stimulating differentiation and mineralization of osteoblasts. Further, these three compounds did not show any estrogen agonistic activity, however had mild estrogen antagonistic effect. Out of the three compounds, 3c was found to maximally increase the mineralization of bone marrow osteoprogenitor cells. Compound 3c also robustly increased the mRNA levels of osteogenic genes including bone morphogenetic protein-2 and osteocalcin in osteoblasts. Unlike daidzein, 3c did not inhibit osteoclastogenesis. Collectively, we demonstrate osteogenic activity of daidzein analogs at significantly lower concentrations than daidzein. (C) 2010 Elsevier Ltd. All rights reserved.