(+)-(S)-N²-(tert-butoxycarbonyl)-N¹-(2,6-dimethylphenyl)-N¹-ethylalaninamide | 936628-15-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-(S)-N²-(tert-butoxycarbonyl)-N¹-(2,6-dimethylphenyl)-N¹-ethylalaninamide
• 英文别名: tert-butyl N-[(2S)-1-(N-ethyl-2,6-dimethylanilino)-1-oxopropan-2-yl]carbamate
• CAS: 936628-15-8
• 化学式: C₁₈H₂₈N₂O₃
• 分子量: 320.432
• InChiKey: BSCKCQBKIREVJK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(S)-N²-(tert-butoxycarbonyl)-N¹-(2,6-dimethylphenyl)-N¹-ethylalaninamide 在 盐酸 作用下， 以 乙醚 为溶剂， 以50%的产率得到(2S)-2-amino-N-(2,6-dimethylphenyl)-N-ethylpropanamide;hydrochloride
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Chiral α-Aminoanilides with Central Antinociceptive Activity

  摘要：

  Tocainide and related optically active chiral alpha-aminoanilides were synthesized and tested in vivo via the hot plate test to evaluate their central analgesic action. The aims of the study were to verify if a) the increase in lipophilicity, obtained by the introduction of an alkyl group on the steric center (3f-i), and the replacement of the C=O group with the C=S (10) group as well as the introduction of a methyl or ethyl group on the amidic nitrogen atom (8a-c) would produce an increase in central analgesic efficacy with respect to Tocainide; b) the 2,6-xylidide moiety is crucial for high analgesic activity (3b-e); c) the hydrogen atom bonded to the amidic nitrogen moiety is an essential pharmacophoric element for analgesic activity. Among all the synthesized compounds, 3f showed antinociceptive properties with a good enantioselective index.

  DOI：

  10.1021/jm061078e
• 作为产物：
  描述：

  2-(t-butoxycarbonyloxyimino)-2-phenylacetonitrile 在 barium dihydroxide 、 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline 、 三乙胺 作用下， 以 1,4-二氧六环 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 (+)-(S)-N²-(tert-butoxycarbonyl)-N¹-(2,6-dimethylphenyl)-N¹-ethylalaninamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Chiral α-Aminoanilides with Central Antinociceptive Activity

  摘要：

  Tocainide and related optically active chiral alpha-aminoanilides were synthesized and tested in vivo via the hot plate test to evaluate their central analgesic action. The aims of the study were to verify if a) the increase in lipophilicity, obtained by the introduction of an alkyl group on the steric center (3f-i), and the replacement of the C=O group with the C=S (10) group as well as the introduction of a methyl or ethyl group on the amidic nitrogen atom (8a-c) would produce an increase in central analgesic efficacy with respect to Tocainide; b) the 2,6-xylidide moiety is crucial for high analgesic activity (3b-e); c) the hydrogen atom bonded to the amidic nitrogen moiety is an essential pharmacophoric element for analgesic activity. Among all the synthesized compounds, 3f showed antinociceptive properties with a good enantioselective index.

  DOI：

  10.1021/jm061078e

文献信息

• Synthesis and Biological Evaluation of Chiral α-Aminoanilides with Central Antinociceptive Activity
  作者：Filomena Corbo、Carlo Franchini、Giovanni Lentini、Marilena Muraglia、Carla Ghelardini、Rosanna Matucci、Nicoletta Galeotti、Elisa Vivoli、Vincenzo Tortorella

  DOI：10.1021/jm061078e

  日期：2007.4.1

  Tocainide and related optically active chiral alpha-aminoanilides were synthesized and tested in vivo via the hot plate test to evaluate their central analgesic action. The aims of the study were to verify if a) the increase in lipophilicity, obtained by the introduction of an alkyl group on the steric center (3f-i), and the replacement of the C=O group with the C=S (10) group as well as the introduction of a methyl or ethyl group on the amidic nitrogen atom (8a-c) would produce an increase in central analgesic efficacy with respect to Tocainide; b) the 2,6-xylidide moiety is crucial for high analgesic activity (3b-e); c) the hydrogen atom bonded to the amidic nitrogen moiety is an essential pharmacophoric element for analgesic activity. Among all the synthesized compounds, 3f showed antinociceptive properties with a good enantioselective index.