7-(3-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)-2-hydroxypropoxy)-4-phenyl-2H-chromen-2-one | 1338325-74-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 7-(3-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)-2-hydroxypropoxy)-4-phenyl-2H-chromen-2-one
• 英文别名: 7-(3-(4-(3-(6-fluorobenzisoxazole)-1-piperidyl)-2-hydroxylpropoxy))-4-phenyl-2H-benzopyran-2-one；7-(3-(4-(6-fluorobenzoisoxazol-3-yl)-1-piperidyl)-2-hydroxypropoxy)-4-phenyl-2H-benzopyran-2-one；7-[3-[4-(6-Fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]-2-hydroxypropoxy]-4-phenylchromen-2-one
• CAS: 1338325-74-8
• 化学式: C₃₀H₂₇FN₂O₅
• 分子量: 514.553
• InChiKey: NGQMIUZGTLTNIT-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C
• 沸点：
  738.3±60.0 °C(predicted)
• 密度：
  1.332±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  85
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-羟基-4-苯基香豆素 在 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 7-(3-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)-2-hydroxypropoxy)-4-phenyl-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

文献信息

• BENZOPYRONE DERIVATIVE AND USE THEREOF
  申请人：Zhang Guisen

  公开号：US20140113911A1

  公开（公告）日：2014-04-24

  The present invention relates to the field of pharmaceutical chemistry, and in particular, to a benzopyrone derivative and a use thereof. The benzopyrone derivative is compound having a structure of formula (I) or a pharmaceutically acceptable salt thereof. It has been found by experiments that, this type of compounds is useful in prevention or treatment of neuropsychical diseases.

  本发明涉及制药化学领域，具体地说，涉及一种苯并吡喃衍生物及其用途。该苯并吡喃衍生物是具有结构式(I)或其药用可接受盐的化合物。经实验证明，这类化合物在预防或治疗神经精神疾病方面具有用途。
• US9315496B2
  申请人：——

  公开号：US9315496B2

  公开（公告）日：2016-04-19