N-benzyloxy-N-(2,3-dimethylphenyl)proline amide | 250697-64-4

• 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: N-benzyloxy-N-(2,3-dimethylphenyl)proline amide
• 英文别名: benzyl (2S)-2-[(2,3-dimethylphenyl)carbamoyl]pyrrolidine-1-carboxylate
• CAS: 250697-64-4
• 化学式: C₂₁H₂₄N₂O₃
• 分子量: 352.433
• InChiKey: HHGPDSCFCIJXTJ-IBGZPJMESA-N

物化性质

• 沸点：
  542.8±50.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  N-benzyloxy-N-(2,3-dimethylphenyl)proline amide 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 氯甲酸异丁酯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 生成 N-(3-tert-butoxycarbonylaminopropionyl)-N-(2,3-dimethylphenyl)proline amide
  参考文献：
  名称：

  Synthesis and evaluation of homofarnesoyl-substituted CAAX-peptidomimetics as farnesyltransferase inhibitors and antiproliferative agents

  摘要：

  Several CAAX-peptidomimetics were linked to homofarnesoic acid via a beta-alanyl spacer with the intention to obtain a novel type of bisubstrate analogue farnesyltransferase inhibitors. However, the compounds were found to be only weakly active in the farnesyltransferase inhibition assay. Nevertheless, they displayed antiproliferative activity against different tumor cell lines in the low micromolar range. Replacement of the beta-alanine moiety by aspartic acid-1-methyl ester resulted in a compound which inhibited the farnesyltransferase with an IC50 of 860 nM. The corresponding free acid showed a eightfold loss in activity (IC50 = 6.9 microM).

  DOI：

  10.1016/s0968-0896(99)00165-0
• 作为产物：
  描述：

  2,3-二甲基苯胺 、 N-苄氧羰基-L-脯氨酸 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 N-benzyloxy-N-(2,3-dimethylphenyl)proline amide
  参考文献：
  名称：

  Synthesis and evaluation of homofarnesoyl-substituted CAAX-peptidomimetics as farnesyltransferase inhibitors and antiproliferative agents

  摘要：

  Several CAAX-peptidomimetics were linked to homofarnesoic acid via a beta-alanyl spacer with the intention to obtain a novel type of bisubstrate analogue farnesyltransferase inhibitors. However, the compounds were found to be only weakly active in the farnesyltransferase inhibition assay. Nevertheless, they displayed antiproliferative activity against different tumor cell lines in the low micromolar range. Replacement of the beta-alanine moiety by aspartic acid-1-methyl ester resulted in a compound which inhibited the farnesyltransferase with an IC50 of 860 nM. The corresponding free acid showed a eightfold loss in activity (IC50 = 6.9 microM).

  DOI：

  10.1016/s0968-0896(99)00165-0

文献信息

• Synthesis and evaluation of homofarnesoyl-substituted CAAX-peptidomimetics as farnesyltransferase inhibitors and antiproliferative agents
  作者：Martin Schlitzer、Isabel Sattler、Hans-Martin Dahse

  DOI：10.1016/s0968-0896(99)00165-0

  日期：1999.9

  Several CAAX-peptidomimetics were linked to homofarnesoic acid via a beta-alanyl spacer with the intention to obtain a novel type of bisubstrate analogue farnesyltransferase inhibitors. However, the compounds were found to be only weakly active in the farnesyltransferase inhibition assay. Nevertheless, they displayed antiproliferative activity against different tumor cell lines in the low micromolar range. Replacement of the beta-alanine moiety by aspartic acid-1-methyl ester resulted in a compound which inhibited the farnesyltransferase with an IC50 of 860 nM. The corresponding free acid showed a eightfold loss in activity (IC50 = 6.9 microM).