7-(4-bromobutoxy)-6-methyl-2,3-dihydrocyclopenta[c]chromen-4(1H)-one | 1578300-97-6

• 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: 7-(4-bromobutoxy)-6-methyl-2,3-dihydrocyclopenta[c]chromen-4(1H)-one
• CAS: 1578300-97-6
• 化学式: C₁₇H₁₉BrO₃
• 分子量: 351.24
• InChiKey: KTXAZGACBMSPRX-UHFFFAOYSA-N

物化性质

• 熔点：
  104-106 °C
• 沸点：
  502.5±50.0 °C(predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  7-(4-bromobutoxy)-6-methyl-2,3-dihydrocyclopenta[c]chromen-4(1H)-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80.3%的产率得到7-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)butoxy)-6-methyl-2,3-dihydrocyclopenta[c]chromen-4(1H)-one
  参考文献：
  名称：

  Synthesis and evaluation of new coumarin derivatives as potential atypical antipsychotics

  摘要：

  In this paper, we report the synthesis of novel, potential antipsychotic coumarin derivatives combining potent dopamine D-2, D-3 and serotonin 5-HT1A 5-HT(2)A receptors properties. We describe the structure activity relationship that leads us to the promising derivative: 7-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl) piperidin-1-yl)butoxy)-6-methyl-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 27. The unique pharmacological features of compound 27 are a high affinity for dopamine D-2, D-3 and serotonin 5-HT1A, 5-HT2A receptors, together with a low affinity for H-1 receptor (to reduce the risk of obesity under chronic treatment). In animal models, compound 27 inhibited apomorphine-induced climbing and MK-801-induced hyperactivity without observable catalepsy at the highest dose tested. In particular, compound 27 was more potent than clozapine. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.012
• 作为产物：
  描述：

  2-甲氧羰基环戊酮 在 bismuth (III) nitrate pentahydrate 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 7-(4-bromobutoxy)-6-methyl-2,3-dihydrocyclopenta[c]chromen-4(1H)-one
  参考文献：
  名称：

  Synthesis and evaluation of new coumarin derivatives as potential atypical antipsychotics

  摘要：

  In this paper, we report the synthesis of novel, potential antipsychotic coumarin derivatives combining potent dopamine D-2, D-3 and serotonin 5-HT1A 5-HT(2)A receptors properties. We describe the structure activity relationship that leads us to the promising derivative: 7-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl) piperidin-1-yl)butoxy)-6-methyl-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 27. The unique pharmacological features of compound 27 are a high affinity for dopamine D-2, D-3 and serotonin 5-HT1A, 5-HT2A receptors, together with a low affinity for H-1 receptor (to reduce the risk of obesity under chronic treatment). In animal models, compound 27 inhibited apomorphine-induced climbing and MK-801-induced hyperactivity without observable catalepsy at the highest dose tested. In particular, compound 27 was more potent than clozapine. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.012