2-(5-benzyloxy-2-bromophenyl)nitroethylene | 262450-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(5-benzyloxy-2-bromophenyl)nitroethylene
• 英文别名: 1-bromo-2-[(E)-2-nitroethenyl]-4-phenylmethoxybenzene
• CAS: 262450-97-5
• 化学式: C₁₅H₁₂BrNO₃
• 分子量: 334.169
• InChiKey: SOIDERINIPFAFH-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-(5-benzyloxy-2-bromophenyl)nitroethylene 在 盐酸 、 amalgamated zinc 、 三氯氧磷 作用下， 以 甲醇 、 乙腈 、 xylene 为溶剂， 反应 10.5h， 生成
  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：

  2-溴-5-甲氧基苯甲醛 在 氢溴酸 、 盐酸甲胺 、 sodium carbonate 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 147.0h， 生成 2-(5-benzyloxy-2-bromophenyl)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

• Modulators of peroxisome proliferator activated receptors (ppar)
  申请人：Gossett Stacy Lynn

  公开号：US20050075378A1

  公开（公告）日：2005-04-07

  The present invention is directed to a compound of formula I, and pharmaceutically acceptable salts, solvates, hydrates or stereoisomer thereof, which are useful in treating Syndrome X, Type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, arteriosclerosis, and other disorders related to Syndrome X as well as cardiovascular diseases.

  本发明涉及一种I式化合物，以及其药学上可接受的盐、溶剂、水合物或立体异构体，该化合物在治疗X综合征、2型糖尿病、高血糖、高脂血症、肥胖症、凝血障碍、高血压、动脉硬化以及与X综合征相关的其他疾病以及心血管疾病方面有用。
• MODULATORS OF PEROXISOME PROLIFERATOR ACTIVATED RECEPTORS (PPAR)
  申请人：Gossett Lynn Stacy

  公开号：US20080167310A1

  公开（公告）日：2008-07-10

  The present invention is directed to a compound of formula I, and pharmaceutically acceptable salts, solvates, hydrates or stereoisomer thereof, which are useful in treating Syndrome X, Type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, arteriosclerosis, and other disorders related to Syndrome X as well as cardiovascular diseases.

  本发明涉及公式I的化合物及其药学上可接受的盐、溶剂化合物、水合物或立体异构体，其可用于治疗X综合症、II型糖尿病、高血糖、高血脂、肥胖症、凝血异常、高血压、动脉硬化以及与X综合症和心血管疾病有关的其他疾病。
• US7282501B2
  申请人：——

  公开号：US7282501B2

  公开（公告）日：2007-10-16
• [EN] MODULATORS OF PEROXISOME PROLIFERATOR ACTIVATED RECEPTORS (PPAR)<br/>[FR] MODULATEURS DES RECEPTEURS ACTIVES PAR LES PROLIFERATEURS DU PEROXISOME (PPAR)
  申请人：LILLY CO ELI

  公开号：WO2002100403A1

  公开（公告）日：2002-12-19

  The present invention is directed to a compound of formula I, and pharmaceutically acceptable salts, solvates, hydrates or stereoisomer thereof, which are useful in treating Syndrome X, Type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, arteriosclerosis, and other disorders related to Syndrome X as well as cardiovascular diseases.
• 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.