(E)-7-((4-bromobut-2-en-1-yl)oxy)-4-methyl-2H-chromen-2-one | 1440946-73-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (E)-7-((4-bromobut-2-en-1-yl)oxy)-4-methyl-2H-chromen-2-one
• 英文别名: 7-(4-bromobutenyloxy)-4-methylbenzopyran-2-one；7-[(E)-4-bromobut-2-enoxy]-4-methylchromen-2-one
• CAS: 1440946-73-5
• 化学式: C₁₄H₁₃BrO₃
• 分子量: 309.159
• InChiKey: OESBOYRTFJVNDQ-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-7-((4-bromobut-2-en-1-yl)oxy)-4-methyl-2H-chromen-2-one 、 6-氟-3-(哌啶-4-基)苯并[D]异恶唑 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 以80.8%的产率得到(E)-7-((4-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)but-2-en-1-yl)oxy)-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and Biological Investigation of Coumarin Piperazine (Piperidine) Derivatives as Potential Multireceptor Atypical Antipsychotics

  摘要：

  The discovery and synthesis of potential and novel antipsychotic coumarin derivatives, associated with potent dopamine 132, D3, and serotonin S-HT1A and S-HT2A, receptor properties, are the focus of the present article. The most-promising derivative was 7-(4-(4-(6-fluorobenzo[d]-isoxazol-3-yl)-piperidin-1-yl)butoxy)-4-methyl-8-chloro-2H- chromen-2-one (17m). This derivative possesses unique pharmacological features, including high affinity for dopamine D-2 and D-3 and serotonin S-HT1A and 5-HT2A receptors. Moreover, it possesses low affinity for S-HT2C and H-1 receptors (to reduce the risk of obesity associated with chronic treatment) and hERG channels (to reduce the incidence of torsade des pointes). In animal models, compound 17m inhibited apomorphine-induced climbing behavior, MK-801-induced hyperactivity, and the conditioned avoidance response without observable catalepsy at the highest dose tested. Further, fewer preclinical adverse events were noted with 17m compared with risperidone in assays that measured prolactin secretion and weight gain. Acceptable pharmacokinetic properties were also noted with 17m. Taken together, 17m may constitute a novel class of drugs for the treatment of schizophrenia.

  DOI：

  10.1021/jm400408r
• 作为产物：
  描述：

  间苯二酚 在 硫酸 、 potassium carbonate 、 potassium hydroxide 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 (E)-7-((4-bromobut-2-en-1-yl)oxy)-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  化感化学品中有希望的杀菌剂：伞形酮衍生物的合成及其结构-活性关系。

  摘要：

  伞形酮在我们先前的研究中被发现是一种重要的化感物质，但其活性和结构的贡献尚未揭示。在这项研究中，合成了一系列类似物以确定伞形酮的骨架并检查其杀真菌活性。此外，用三种植物寄生真菌进行了有针对性的修饰，以检查先导化合物。在测试的化合物中，发现化合物2f和10具有出色的抗真菌活性，在100 ug / mL时抑制率超过80％。该研究证明伞形酮可以作为发现杀菌剂的有前途的骨架。此外，其一级结构活性关系为将来发现基于天然产物的新型杀菌剂提供了很好的指导。

  DOI：

  10.3390/molecules23113002

文献信息

• Synthesis and Biological Investigation of Coumarin Piperazine (Piperidine) Derivatives as Potential Multireceptor Atypical Antipsychotics
  作者：Yin Chen、Songlin Wang、Xiangqing Xu、Xin Liu、Minquan Yu、Song Zhao、Shicheng Liu、Yinli Qiu、Tan Zhang、Bi-Feng Liu、Guisen Zhang

  DOI：10.1021/jm400408r

  日期：2013.6.13

  The discovery and synthesis of potential and novel antipsychotic coumarin derivatives, associated with potent dopamine 132, D3, and serotonin S-HT1A and S-HT2A, receptor properties, are the focus of the present article. The most-promising derivative was 7-(4-(4-(6-fluorobenzo[d]-isoxazol-3-yl)-piperidin-1-yl)butoxy)-4-methyl-8-chloro-2H- chromen-2-one (17m). This derivative possesses unique pharmacological features, including high affinity for dopamine D-2 and D-3 and serotonin S-HT1A and 5-HT2A receptors. Moreover, it possesses low affinity for S-HT2C and H-1 receptors (to reduce the risk of obesity associated with chronic treatment) and hERG channels (to reduce the incidence of torsade des pointes). In animal models, compound 17m inhibited apomorphine-induced climbing behavior, MK-801-induced hyperactivity, and the conditioned avoidance response without observable catalepsy at the highest dose tested. Further, fewer preclinical adverse events were noted with 17m compared with risperidone in assays that measured prolactin secretion and weight gain. Acceptable pharmacokinetic properties were also noted with 17m. Taken together, 17m may constitute a novel class of drugs for the treatment of schizophrenia.
• Promising Fungicides from Allelochemicals: Synthesis of Umbelliferone Derivatives and Their Structure–Activity Relationships
  作者：Le Pan、Dongyu Lei、Lu Jin、Yuan He、Qingqing Yang

  DOI：10.3390/molecules23113002

  日期：——

  of its activity and structure has not yet been revealed. In this study, a series of analogues were synthesized to determine the skeleton of umbelliferone and examine its fungicidal activity. Furthermore, targeted modifications were conducted with three plant parasitic fungi to examine the lead compounds. Among those tested, compounds 2f and 10 were found to show excellent antifungal activity with an

  伞形酮在我们先前的研究中被发现是一种重要的化感物质，但其活性和结构的贡献尚未揭示。在这项研究中，合成了一系列类似物以确定伞形酮的骨架并检查其杀真菌活性。此外，用三种植物寄生真菌进行了有针对性的修饰，以检查先导化合物。在测试的化合物中，发现化合物2f和10具有出色的抗真菌活性，在100 ug / mL时抑制率超过80％。该研究证明伞形酮可以作为发现杀菌剂的有前途的骨架。此外，其一级结构活性关系为将来发现基于天然产物的新型杀菌剂提供了很好的指导。