ω-(dibenzylamino)-4-benzyloxy-3-nitroacetophenone | 173283-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ω-(dibenzylamino)-4-benzyloxy-3-nitroacetophenone
• 英文别名: 2-(Dibenzylamino)-1-(3-nitro-4-phenylmethoxyphenyl)ethanone
• CAS: 173283-38-0
• 化学式: C₂₉H₂₆N₂O₄
• 分子量: 466.536
• InChiKey: JAUCNJPPDCKVIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ω-(dibenzylamino)-4-benzyloxy-3-nitroacetophenone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 1-(4-benzyloxy-3-nitrophenyl)-2-dibenzylaminoethanol
  参考文献：
  名称：

  Role of the benzylic hydroxyl group of adrenergic catecholamines in eliciting α-adrenergic activity. Synthesis and α1- and α2-adrenergic activity of 3-phenyl-3-piperidinols and their desoxy analogs

  摘要：

  In order to contribute to the definition of the role played by the benzylic hydroxyl group of adrenergic catecholamines in eliciting alpha-adrenergic activity, certain 3-phenyl-3-piperidinols (PPOs, 4) and their corresponding desoxy 3-phenylpiperidine analogs (PPEs, 6) were synthesized and tested for their alpha(1)- and alpha(2)-adrenergic activity be means of functional tests on isolated preparations. As regards the alpha(1)-adrenergic activity, the values of the activity indices of the cyclic catecholic compounds (PPO 4a and PPE 6a) indicate that the benzylic hydroxyl does not play an essential role, provided that the other two active groups are in the pharmacophoric conformation. However, the fact that none of the other non-catecholic cyclic analogs are active on the alpha(1)-receptor does not allow us to generalize this observation. As regards the alpha(2)-adrenergic activity, the high values of the activity indices of PPEs 6, compared with those of the corresponding 1-phenyl-2-aminoethanols (PAEs, 3), PPOs (4) and 2-phenylethylamines (PEAs, 5), confirm that when the aromatic moiety and the amino group are constrained into the pharmacophoric relationship, the presence of the alcoholic hydroxyl is not only unnecessary for the purposes of the expression of the activity at the level of the alpha(2)-adrenoceptor, but often has a negative effect.

  DOI：

  10.1016/0223-5234(96)88306-1
• 作为产物：
  描述：

  3'-硝基-4'-苄氧基-2-溴苯乙酮 、 二苄胺 以 苯 为溶剂， 反应 72.0h， 生成 ω-(dibenzylamino)-4-benzyloxy-3-nitroacetophenone
  参考文献：
  名称：

  Role of the benzylic hydroxyl group of adrenergic catecholamines in eliciting α-adrenergic activity. Synthesis and α1- and α2-adrenergic activity of 3-phenyl-3-piperidinols and their desoxy analogs

  摘要：

  In order to contribute to the definition of the role played by the benzylic hydroxyl group of adrenergic catecholamines in eliciting alpha-adrenergic activity, certain 3-phenyl-3-piperidinols (PPOs, 4) and their corresponding desoxy 3-phenylpiperidine analogs (PPEs, 6) were synthesized and tested for their alpha(1)- and alpha(2)-adrenergic activity be means of functional tests on isolated preparations. As regards the alpha(1)-adrenergic activity, the values of the activity indices of the cyclic catecholic compounds (PPO 4a and PPE 6a) indicate that the benzylic hydroxyl does not play an essential role, provided that the other two active groups are in the pharmacophoric conformation. However, the fact that none of the other non-catecholic cyclic analogs are active on the alpha(1)-receptor does not allow us to generalize this observation. As regards the alpha(2)-adrenergic activity, the high values of the activity indices of PPEs 6, compared with those of the corresponding 1-phenyl-2-aminoethanols (PAEs, 3), PPOs (4) and 2-phenylethylamines (PEAs, 5), confirm that when the aromatic moiety and the amino group are constrained into the pharmacophoric relationship, the presence of the alcoholic hydroxyl is not only unnecessary for the purposes of the expression of the activity at the level of the alpha(2)-adrenoceptor, but often has a negative effect.

  DOI：

  10.1016/0223-5234(96)88306-1

文献信息

• Role of the benzylic hydroxyl group of adrenergic catecholamines in eliciting α-adrenergic activity. Synthesis and α1- and α2-adrenergic activity of 3-phenyl-3-piperidinols and their desoxy analogs
  作者：B Macchia、M Macchia、C Manera、E Martinotti、S Nencetti、E Orlandini、A Rossello、R Scatizzi

  DOI：10.1016/0223-5234(96)88306-1

  日期：1995.1

  In order to contribute to the definition of the role played by the benzylic hydroxyl group of adrenergic catecholamines in eliciting alpha-adrenergic activity, certain 3-phenyl-3-piperidinols (PPOs, 4) and their corresponding desoxy 3-phenylpiperidine analogs (PPEs, 6) were synthesized and tested for their alpha(1)- and alpha(2)-adrenergic activity be means of functional tests on isolated preparations. As regards the alpha(1)-adrenergic activity, the values of the activity indices of the cyclic catecholic compounds (PPO 4a and PPE 6a) indicate that the benzylic hydroxyl does not play an essential role, provided that the other two active groups are in the pharmacophoric conformation. However, the fact that none of the other non-catecholic cyclic analogs are active on the alpha(1)-receptor does not allow us to generalize this observation. As regards the alpha(2)-adrenergic activity, the high values of the activity indices of PPEs 6, compared with those of the corresponding 1-phenyl-2-aminoethanols (PAEs, 3), PPOs (4) and 2-phenylethylamines (PEAs, 5), confirm that when the aromatic moiety and the amino group are constrained into the pharmacophoric relationship, the presence of the alcoholic hydroxyl is not only unnecessary for the purposes of the expression of the activity at the level of the alpha(2)-adrenoceptor, but often has a negative effect.