2-(3-bromo-5-methoxyphenyl)nitroethylene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-bromo-5-methoxyphenyl)nitroethylene
• 英文别名: 1-bromo-3-methoxy-5-[(E)-2-nitroethenyl]benzene
• 化学式: C₉H₈BrNO₃
• 分子量: 258.071
• InChiKey: ARTOMMCJVZYZPP-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-bromo-5-methoxyphenyl)nitroethylene 在 盐酸 、 amalgamated zinc 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 2-(3-溴-5-甲氧基苯基)乙胺
  参考文献：
  名称：

  Binding and Preliminary Evaluation of 5-Hydroxy- and 10-Hydroxy-2,3,12,12a-tetrahydro-1H-[1]benzoxepino[2,3,4-ij]isoquinolines as Dopamine Receptor Ligands

  摘要：

  The N-methyl, N-ethyl, and N-n-propyl derivatives of 5-hydoxy- and 10-hydroxy-2,3,12,12a-tetrahydro-1H-[1]benzoxepino[2,3,4-ij]isoquinolines were were prepared as monophenolic ligands for the dopamine receptor and evaluated for their affinity at D-1-like and D-2-like subtypes. All compounds showed very low D-1 affinities. This could be ascribed to the absence of a catechol nucleus or of the beta-phenyldopamine pharmacophore. Only the N-methyl-5-hydroxy- (5a), N-methyl-10-hydroxy- (6a), and N-methyl-4-bromo-10-methoxy-2,3,12,12a-tetrahydro-1H-[1]-benzoxepino[2,3,4-ij]isoquinolines (26a) bound the D-2 receptors with low affinity, in the same range as dopamine. In compounds 5a and so, the 2-(3-hydroxyphenyl)ethylamine moiety does not meet the requirements of the D-2 agonist pharmacophore: namely, the 2-(3-hydroxyphenyl)ethylamine does not reach the trans, fully extended conformation. The three compounds did not interact with recombinant human D-4 receptors, and only 5a showed low affinity for rat recombinant D-3 receptors. Analysis of the influence of Na+ on [H-3]spiperone binding showed that 5a displays a potential dopamine D-2 agonist profile, whereas 6a probably has a dopamine D-2 antagonist activity. The D-2 agonist activity of 5a was proved by the effects on prolactin release from primary cultures of rat anterior pituitary cells.

  DOI：

  10.1021/jm991034o
• 作为产物：
  描述：

  3-溴-5-甲氧基苯甲酸 在 lithium aluminium tetrahydride 、 盐酸甲胺 、 pyridinium chlorochromate 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 2-(3-bromo-5-methoxyphenyl)nitroethylene
  参考文献：
  名称：

  Binding and Preliminary Evaluation of 5-Hydroxy- and 10-Hydroxy-2,3,12,12a-tetrahydro-1H-[1]benzoxepino[2,3,4-ij]isoquinolines as Dopamine Receptor Ligands

  摘要：

  The N-methyl, N-ethyl, and N-n-propyl derivatives of 5-hydoxy- and 10-hydroxy-2,3,12,12a-tetrahydro-1H-[1]benzoxepino[2,3,4-ij]isoquinolines were were prepared as monophenolic ligands for the dopamine receptor and evaluated for their affinity at D-1-like and D-2-like subtypes. All compounds showed very low D-1 affinities. This could be ascribed to the absence of a catechol nucleus or of the beta-phenyldopamine pharmacophore. Only the N-methyl-5-hydroxy- (5a), N-methyl-10-hydroxy- (6a), and N-methyl-4-bromo-10-methoxy-2,3,12,12a-tetrahydro-1H-[1]-benzoxepino[2,3,4-ij]isoquinolines (26a) bound the D-2 receptors with low affinity, in the same range as dopamine. In compounds 5a and so, the 2-(3-hydroxyphenyl)ethylamine moiety does not meet the requirements of the D-2 agonist pharmacophore: namely, the 2-(3-hydroxyphenyl)ethylamine does not reach the trans, fully extended conformation. The three compounds did not interact with recombinant human D-4 receptors, and only 5a showed low affinity for rat recombinant D-3 receptors. Analysis of the influence of Na+ on [H-3]spiperone binding showed that 5a displays a potential dopamine D-2 agonist profile, whereas 6a probably has a dopamine D-2 antagonist activity. The D-2 agonist activity of 5a was proved by the effects on prolactin release from primary cultures of rat anterior pituitary cells.

  DOI：

  10.1021/jm991034o

文献信息

• Binding and Preliminary Evaluation of 5-Hydroxy- and 10-Hydroxy-2,3,12,12a-tetrahydro-1<i>H</i>-[1]benzoxepino[2,3,4-<i>i</i><i>j</i>]isoquinolines as Dopamine Receptor Ligands
  作者：Francesco Claudi、Antonio Di Stefano、Fabrizio Napolitani、Gian Mario Cingolani、Gianfabio Giorgioni、Josè A. Fontenla、Gisela Y. Montenegro、Maria E. Rivas、Elizabeth Rosa、Barbara Michelotto、Giustino Orlando、Luigi Brunetti

  DOI：10.1021/jm991034o

  日期：2000.2.1

  The N-methyl, N-ethyl, and N-n-propyl derivatives of 5-hydoxy- and 10-hydroxy-2,3,12,12a-tetrahydro-1H-[1]benzoxepino[2,3,4-ij]isoquinolines were were prepared as monophenolic ligands for the dopamine receptor and evaluated for their affinity at D-1-like and D-2-like subtypes. All compounds showed very low D-1 affinities. This could be ascribed to the absence of a catechol nucleus or of the beta-phenyldopamine pharmacophore. Only the N-methyl-5-hydroxy- (5a), N-methyl-10-hydroxy- (6a), and N-methyl-4-bromo-10-methoxy-2,3,12,12a-tetrahydro-1H-[1]-benzoxepino[2,3,4-ij]isoquinolines (26a) bound the D-2 receptors with low affinity, in the same range as dopamine. In compounds 5a and so, the 2-(3-hydroxyphenyl)ethylamine moiety does not meet the requirements of the D-2 agonist pharmacophore: namely, the 2-(3-hydroxyphenyl)ethylamine does not reach the trans, fully extended conformation. The three compounds did not interact with recombinant human D-4 receptors, and only 5a showed low affinity for rat recombinant D-3 receptors. Analysis of the influence of Na+ on [H-3]spiperone binding showed that 5a displays a potential dopamine D-2 agonist profile, whereas 6a probably has a dopamine D-2 antagonist activity. The D-2 agonist activity of 5a was proved by the effects on prolactin release from primary cultures of rat anterior pituitary cells.