N,N-dipropyl-4-nitro-3-methyl-phenylacetamide | 176689-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-dipropyl-4-nitro-3-methyl-phenylacetamide
• 英文别名: 2-(3-methyl-4-nitrophenyl)-N,N-dipropylacetamide
• CAS: 176689-27-3
• 化学式: C₁₅H₂₂N₂O₃
• 分子量: 278.351
• InChiKey: LVKKUAOAECBPJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-dipropyl-4-nitro-3-methyl-phenylacetamide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 4,4'-bis(2-dipropylaminoethyl)-2,2'-dimethylazobenzene
  参考文献：
  名称：

  Partial dopamine receptor agonists with different degrees of intrinsic activity within a series of 2-(4-aminophenyl)-N,N-dipropylethylamine derivatives: synthetic chemistry and structure-activity relationships

  摘要：

  A series of 2-(4-aminophenyl)-N,N-dipropylethylamine derivatives were synthesized and tested for in vivo intrinsic activity at brain dopamine receptors in the rat. Differences in the sensitivity of dopamine receptors pre and post-synaptically in the reserpine-treated rat were used to estimate the intrinsic activity of the various compounds as dopamine receptor agonists. Thus, the ability of the compounds to antagonize reserpine-induced increase in neostriatal dopamine synthesis and the suppression of spontaneous locomotor activity were taken as pre-and post-synaptic indices, respectively. The compounds in the present series display a gradient of intrinsic activity depending on the substituents in the aromatic ring. The presence of an amino group or an appropriate acylamino group in the 4-position was found to be critical for the biological activity of these compounds as agonists or antagonists. The introduction of halogen or a trifluoromethyl group In the 3-position resulted in high intrinsic activity (ie, agonist activity). The incorporation of a methyl group in the 3-position or halogens in the 3,5-positions resulted in a gradual decrease in intrinsic activity at rat brain dopamine receptors resulting in a series of compounds ranging from a full agonist to dopamine receptor blockade.

  DOI：

  10.1016/0223-5234(96)80446-6
• 作为产物：
  描述：

  2-(3-甲基-4-硝基苯基)乙酸 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 N,N-dipropyl-4-nitro-3-methyl-phenylacetamide
  参考文献：
  名称：

  Partial dopamine receptor agonists with different degrees of intrinsic activity within a series of 2-(4-aminophenyl)-N,N-dipropylethylamine derivatives: synthetic chemistry and structure-activity relationships

  摘要：

  A series of 2-(4-aminophenyl)-N,N-dipropylethylamine derivatives were synthesized and tested for in vivo intrinsic activity at brain dopamine receptors in the rat. Differences in the sensitivity of dopamine receptors pre and post-synaptically in the reserpine-treated rat were used to estimate the intrinsic activity of the various compounds as dopamine receptor agonists. Thus, the ability of the compounds to antagonize reserpine-induced increase in neostriatal dopamine synthesis and the suppression of spontaneous locomotor activity were taken as pre-and post-synaptic indices, respectively. The compounds in the present series display a gradient of intrinsic activity depending on the substituents in the aromatic ring. The presence of an amino group or an appropriate acylamino group in the 4-position was found to be critical for the biological activity of these compounds as agonists or antagonists. The introduction of halogen or a trifluoromethyl group In the 3-position resulted in high intrinsic activity (ie, agonist activity). The incorporation of a methyl group in the 3-position or halogens in the 3,5-positions resulted in a gradual decrease in intrinsic activity at rat brain dopamine receptors resulting in a series of compounds ranging from a full agonist to dopamine receptor blockade.

  DOI：

  10.1016/0223-5234(96)80446-6

文献信息

• Partial dopamine receptor agonists with different degrees of intrinsic activity within a series of 2-(4-aminophenyl)-N,N-dipropylethylamine derivatives: synthetic chemistry and structure-activity relationships
  作者：L Florvall、V Hillegaart、A Malmberg、A Wijkström、S Ahlenius

  DOI：10.1016/0223-5234(96)80446-6

  日期：1996.1

  A series of 2-(4-aminophenyl)-N,N-dipropylethylamine derivatives were synthesized and tested for in vivo intrinsic activity at brain dopamine receptors in the rat. Differences in the sensitivity of dopamine receptors pre and post-synaptically in the reserpine-treated rat were used to estimate the intrinsic activity of the various compounds as dopamine receptor agonists. Thus, the ability of the compounds to antagonize reserpine-induced increase in neostriatal dopamine synthesis and the suppression of spontaneous locomotor activity were taken as pre-and post-synaptic indices, respectively. The compounds in the present series display a gradient of intrinsic activity depending on the substituents in the aromatic ring. The presence of an amino group or an appropriate acylamino group in the 4-position was found to be critical for the biological activity of these compounds as agonists or antagonists. The introduction of halogen or a trifluoromethyl group In the 3-position resulted in high intrinsic activity (ie, agonist activity). The incorporation of a methyl group in the 3-position or halogens in the 3,5-positions resulted in a gradual decrease in intrinsic activity at rat brain dopamine receptors resulting in a series of compounds ranging from a full agonist to dopamine receptor blockade.