N-<4-<(dimethylcarbamoyl)thio>-3-methoxybenzyl>nonanamide | 149555-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-<4-<(dimethylcarbamoyl)thio>-3-methoxybenzyl>nonanamide
• CAS: 149555-76-0
• 化学式: C₂₀H₃₂N₂O₃S
• 分子量: 380.552
• InChiKey: BWYARPVAEFYQMV-UHFFFAOYSA-N

物化性质

• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.64
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-<4-<(dimethylcarbamoyl)thio>-3-methoxybenzyl>nonanamide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以96%的产率得到N-(3-methoxy-4-mercaptobenzyl)nonanamide
  参考文献：
  名称：

  Analogs of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 1. The aromatic "A-region"

  摘要：

  A series of analogues of capsaicin, the pungent principle of chilli peppers, was synthesized and tested in assays for capsaicin-like agonism in vitro. The results of these assays were compared with activities in an acute nociceptive model and a correlation was observed which established that the results of these in vitro assays were predictive of analgesia. Using a modular approach the structure-activity profile of specific regions of capsaicin congeners was established using an in vitro assay measuring Ca-45(2+) uptake into neonatal rat dorsal root ganglia neurones. Substituted benzylnonanamides 2a-z and N-octyl-substituted phenylacetamides 4a-v were made to test the requirements for activity in the aromatic ''A-region'' of the molecule. Compounds with the natural substitution pattern (2b and 4c) and the corresponding catechols (2i and 4g) were the most potent, although the catechols were less potent in vivo. Other substitution patterns have reduced activity. These results have established stringent structural requirements for capsaicin-like activity in this part of the molecule.

  DOI：

  10.1021/jm00068a014
• 作为产物：
  描述：

  4-(氨基甲基)-2-甲氧基苯酚盐酸盐 在 sodium hydride 、 三乙胺 作用下， 反应 0.78h， 生成 N-<4-<(dimethylcarbamoyl)thio>-3-methoxybenzyl>nonanamide
  参考文献：
  名称：

  Analogs of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 1. The aromatic "A-region"

  摘要：

  A series of analogues of capsaicin, the pungent principle of chilli peppers, was synthesized and tested in assays for capsaicin-like agonism in vitro. The results of these assays were compared with activities in an acute nociceptive model and a correlation was observed which established that the results of these in vitro assays were predictive of analgesia. Using a modular approach the structure-activity profile of specific regions of capsaicin congeners was established using an in vitro assay measuring Ca-45(2+) uptake into neonatal rat dorsal root ganglia neurones. Substituted benzylnonanamides 2a-z and N-octyl-substituted phenylacetamides 4a-v were made to test the requirements for activity in the aromatic ''A-region'' of the molecule. Compounds with the natural substitution pattern (2b and 4c) and the corresponding catechols (2i and 4g) were the most potent, although the catechols were less potent in vivo. Other substitution patterns have reduced activity. These results have established stringent structural requirements for capsaicin-like activity in this part of the molecule.

  DOI：

  10.1021/jm00068a014