(1,2,3,4-tetrahydro-1-oxo-6-phenylnaphthalen-3-yl)methyl 4-methylbenzenesulfonate | 1558026-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1,2,3,4-tetrahydro-1-oxo-6-phenylnaphthalen-3-yl)methyl 4-methylbenzenesulfonate
• CAS: 1558026-34-8
• 化学式: C₂₄H₂₂O₄S
• 分子量: 406.502
• InChiKey: JZBLPDKOMRQIJN-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C(Solvent: Cyclohexane)
• 沸点：
  611.8±44.0 °C(predicted)
• 密度：
  1.239±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1,2,3,4-tetrahydro-1-oxo-6-phenylnaphthalen-3-yl)methyl 4-methylbenzenesulfonate 、 6-氟-3-(哌啶-4-基)苯并[D]异恶唑 以 苯 为溶剂， 反应 24.0h， 以38%的产率得到3-[(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)methyl]-3,4-dihydro-6-phenylnaphthalen-1(2H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of a series of aminoalkyl-tetralones and tetralols as dual dopamine/serotonin ligands

  摘要：

  A series of novel alpha-tetralone and a-tetralol derivatives was synthesized, and their binding affinities for 5-HT2A and D-2 receptors, the most important targets implicated in the anti-schizophrenia drug action, were evaluated to elucidate how substitutions in the aromatic ring of the pharmacophore affect to the affinity or selectivity for these receptors. The replacement of the H-7 in the tetrahydronaphthalene system by an amino group resulted in privileged 5-HT2A affinity of the 6-fluorobenzo[d]isoxazol derivative 36 and the alcohol 25 both showing a pK(i) value for 5-HT2A higher than 8.3 and good binding affinities for D-2 receptor leading to a Meltzer's ratio characteristic of an atypical antipsychotic profile. Additionally, a small collection of 3-aminomethyltetralone derivatives was prepared and examined here for their affinities and selectivities as 5-HT2A/D-2 dual ligands. Compound 11 shows the best profile with good pK(i) values for 5-HT2A and D-2 receptors leading to a Meltzer's ratio characteristic of a typical antipsychotic behaviour. These three compounds behaved as competitive antagonists of both 5-HT2A and D-2 receptors, and might be promising pharmacological tools for the investigation of the dual function of the 5HT(2A)-D-2 ligands. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.066
• 作为产物：
  描述：

  3-(methoxycarbonyl)-1,2,3,4-tetrahydro-1-oxonaphthalen-6-yl trifluoromethanesulfonate 在 吡啶 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 lithium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 72.0h， 生成 (1,2,3,4-tetrahydro-1-oxo-6-phenylnaphthalen-3-yl)methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis and biological evaluation of a series of aminoalkyl-tetralones and tetralols as dual dopamine/serotonin ligands

  摘要：

  A series of novel alpha-tetralone and a-tetralol derivatives was synthesized, and their binding affinities for 5-HT2A and D-2 receptors, the most important targets implicated in the anti-schizophrenia drug action, were evaluated to elucidate how substitutions in the aromatic ring of the pharmacophore affect to the affinity or selectivity for these receptors. The replacement of the H-7 in the tetrahydronaphthalene system by an amino group resulted in privileged 5-HT2A affinity of the 6-fluorobenzo[d]isoxazol derivative 36 and the alcohol 25 both showing a pK(i) value for 5-HT2A higher than 8.3 and good binding affinities for D-2 receptor leading to a Meltzer's ratio characteristic of an atypical antipsychotic profile. Additionally, a small collection of 3-aminomethyltetralone derivatives was prepared and examined here for their affinities and selectivities as 5-HT2A/D-2 dual ligands. Compound 11 shows the best profile with good pK(i) values for 5-HT2A and D-2 receptors leading to a Meltzer's ratio characteristic of a typical antipsychotic behaviour. These three compounds behaved as competitive antagonists of both 5-HT2A and D-2 receptors, and might be promising pharmacological tools for the investigation of the dual function of the 5HT(2A)-D-2 ligands. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.066