2-hydroxy-N-[(4-methoxyphenyl)methyl]-4-methylpentanamide | 1569843-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-hydroxy-N-[(4-methoxyphenyl)methyl]-4-methylpentanamide
• CAS: 1569843-61-3
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: YOOCMBSBPAIRET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-N-[(4-methoxyphenyl)methyl]-4-methylpentanamide 在 4-二甲氨基吡啶 、 甲基磺酰氯 、 三乙胺 、 三乙烯二胺 、 sodium azide 、 苯并-15-冠醚-5 、 palladium on activated charcoal 、 氢气 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 28.5h， 以84%的产率得到2-amino-N-[(4-methoxyphenyl)methyl]-4-methylpentanamide
  参考文献：
  名称：

  Synthesis of novel, peptidic kinase inhibitors with cytostatic/cytotoxic activity

  摘要：

  The utility of a novel, chemoenzymatic procedure for the stereocontrolled synthesis of small peptides is presented in the preparation and structure optimisation of dipeptides with cytostatic/cytotoxic activity. The method uses Passerini multicomponent reaction for the preparation of racemic scaffold which is then enantioselectively hydrolysed by hydrolytic enzymes. Products of these transformations are further functionalised towards title compounds. Both activity and selectivity towards tumor cells is optimised. Final compound is shown to be an inhibitor of the protein kinase signaling pathway. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.005
• 作为产物：
  描述：

  4-甲氧基异氰酸苄酯 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 2-hydroxy-N-[(4-methoxyphenyl)methyl]-4-methylpentanamide
  参考文献：
  名称：

  Synthesis of novel, peptidic kinase inhibitors with cytostatic/cytotoxic activity

  摘要：

  The utility of a novel, chemoenzymatic procedure for the stereocontrolled synthesis of small peptides is presented in the preparation and structure optimisation of dipeptides with cytostatic/cytotoxic activity. The method uses Passerini multicomponent reaction for the preparation of racemic scaffold which is then enantioselectively hydrolysed by hydrolytic enzymes. Products of these transformations are further functionalised towards title compounds. Both activity and selectivity towards tumor cells is optimised. Final compound is shown to be an inhibitor of the protein kinase signaling pathway. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.005

文献信息

• Synthesis of novel, peptidic kinase inhibitors with cytostatic/cytotoxic activity
  作者：Wiktor Szymanski、Magdalena Zwolinska、Szymon Klossowski、Izabela Młynarczuk-Biały、Łukasz Biały、Tadeusz Issat、Jacek Malejczyk、Ryszard Ostaszewski

  DOI：10.1016/j.bmc.2014.01.005

  日期：2014.3

  The utility of a novel, chemoenzymatic procedure for the stereocontrolled synthesis of small peptides is presented in the preparation and structure optimisation of dipeptides with cytostatic/cytotoxic activity. The method uses Passerini multicomponent reaction for the preparation of racemic scaffold which is then enantioselectively hydrolysed by hydrolytic enzymes. Products of these transformations are further functionalised towards title compounds. Both activity and selectivity towards tumor cells is optimised. Final compound is shown to be an inhibitor of the protein kinase signaling pathway. (C) 2014 Elsevier Ltd. All rights reserved.