N-(5-benzyloxy-3,4,6-trimethylpyridin-2-yl)palmitamide | 1616249-49-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(5-benzyloxy-3,4,6-trimethylpyridin-2-yl)palmitamide
• 英文别名: N-(3,4,6-trimethyl-5-phenylmethoxypyridin-2-yl)hexadecanamide
• CAS: 1616249-49-0
• 化学式: C₃₁H₄₈N₂O₂
• 分子量: 480.734
• InChiKey: GQRUTZBGIAWIPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(5-benzyloxy-3,4,6-trimethylpyridin-2-yl)palmitamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以99%的产率得到N-(5-hydroxy-3,4,6-trimethylpyridin-2-yl)palmitamide
  参考文献：
  名称：

  Synthesis and antiangiogenic activity of 6-amido-2,4,5-trimethylpyridin-3-ols

  摘要：

  We recently reported that 6-aminoalkyl-2,4,5-trimethylpyridin-3-ols, novel series of 6-aminopyridin-3-ol-based antioxidants, have high antiangiogenic activities. In pursuit of wider variety in the analogues, we here report the synthesis and antiangiogenic activities of 6-amidoalkyl-2,4,5-trimethylpyridin-3-ols, which would not be considered excellent antioxidants because of the poorer electron-donating effect of the C(6)-amido group than the corresponding C(6)-amino group. The selected 6-amido compounds showed up to several fold-higher antiangiogenic activities and up to an order of magnitude better antitumor activities in the chick embryo chorioallantoic membrane (CAM) assay than SU4312, a positive control. We also found that paracetamol, as a direct phenolic analogue of our simplest 6-amidopyridin-3-ol, showed a moderate level of antiangiogenic activity. We propose this study will offer a basis for a scaffold of novel angiogenesis inhibitors that can perturb angiogenesis-related pathologies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.005
• 作为产物：
  描述：

  4,5-双(氯甲基)-2-甲基吡啶-3-醇盐酸盐 在 hydrazine hydrate 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 对甲苯磺酰氯 、 间氯过氧苯甲酸 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 N-(5-benzyloxy-3,4,6-trimethylpyridin-2-yl)palmitamide
  参考文献：
  名称：

  Synthesis and antiangiogenic activity of 6-amido-2,4,5-trimethylpyridin-3-ols

  摘要：

  We recently reported that 6-aminoalkyl-2,4,5-trimethylpyridin-3-ols, novel series of 6-aminopyridin-3-ol-based antioxidants, have high antiangiogenic activities. In pursuit of wider variety in the analogues, we here report the synthesis and antiangiogenic activities of 6-amidoalkyl-2,4,5-trimethylpyridin-3-ols, which would not be considered excellent antioxidants because of the poorer electron-donating effect of the C(6)-amido group than the corresponding C(6)-amino group. The selected 6-amido compounds showed up to several fold-higher antiangiogenic activities and up to an order of magnitude better antitumor activities in the chick embryo chorioallantoic membrane (CAM) assay than SU4312, a positive control. We also found that paracetamol, as a direct phenolic analogue of our simplest 6-amidopyridin-3-ol, showed a moderate level of antiangiogenic activity. We propose this study will offer a basis for a scaffold of novel angiogenesis inhibitors that can perturb angiogenesis-related pathologies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.005

文献信息

• Synthesis and activity of N-(5-hydroxy-3,4,6-trimethylpyridin-2-yl)acetamide analogues as anticolitis agents via dual inhibition of TNF-α- and IL-6-induced cell adhesions
  作者：Ujjwala Karmacharya、Sushil Chandra Regmi、Bhuwan Prasad Awasthi、Prakash Chaudhary、Ye Eun Kim、Iyn-Hyang Lee、Tae-gyu Nam、Jung-Ae Kim、Byeong-Seon Jeong

  DOI：10.1016/j.bmcl.2021.128059

  日期：2021.7