6-methoxy-2-(4-phenyl-1-piperazinyl)-4H-1-benzopyran-4-one | 1407546-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-methoxy-2-(4-phenyl-1-piperazinyl)-4H-1-benzopyran-4-one
• 英文别名: 6-Methoxy-2-(4-phenylpiperazin-1-yl)chromen-4-one；6-methoxy-2-(4-phenylpiperazin-1-yl)chromen-4-one
• CAS: 1407546-74-0
• 化学式: C₂₀H₂₀N₂O₃
• 分子量: 336.39
• InChiKey: UIRZFGCVXVHMJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-hydroxy-6-methoxy-2H-chromene-2-thione 在 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 21.0h， 生成 6-methoxy-2-(4-phenyl-1-piperazinyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel piperazine derivatives of flavone as potent anti-inflammatory and antimicrobial agent

  摘要：

  A series of novel 6-methoxy-2-(piperazin-1-yl)-4H-chromen-4-one and 5,7-dimethoxy-2-(piperazin-1-ylmethyl)-4H-chromen-4-one derivatives of biological interest were prepared and screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Among all the compound screened (5a-j and 10k-t), the compounds 5c, 5g, 5h, 10l, 10m, 10n and 10r found to have promising anti-inflammatory activity (up to 65-87% TNF-alpha and 70-93% IL-6 inhibitory activity) at concentration of 10 mu M with reference to standard dexamethasone (71% TNF-a and 84% IL-6 inhibitory activities at 1 mu M) while the compounds5b, 5i, 5j, 10s and 10t found to be potent antimicrobial agent showing even 2 to 2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.071

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.