(S)-3-(3,4-dihydroxyphenyl)-2-(((2S,3R,4R,5R)-2,3,4,5-tetraacetoxy-6-(((S)-2-(6-methoxynaphthalen-2-yl)propanoyl)oxy)hexylidene)amino)propanoic acid | 1251743-78-8

• 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)-3-(3,4-dihydroxyphenyl)-2-(((2S,3R,4R,5R)-2,3,4,5-tetraacetoxy-6-(((S)-2-(6-methoxynaphthalen-2-yl)propanoyl)oxy)hexylidene)amino)propanoic acid
• CAS: 1251743-78-8
• 化学式: C₃₇H₄₁NO₁₅
• 分子量: 739.73
• InChiKey: NQMNWHYDYODNID-BWWYZWMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  53.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  230.85
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  萘普生 在 吡啶 、 氯化亚砜 、 zinc(II) chloride 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 7.0h， 生成 (S)-3-(3,4-dihydroxyphenyl)-2-(((2S,3R,4R,5R)-2,3,4,5-tetraacetoxy-6-(((S)-2-(6-methoxynaphthalen-2-yl)propanoyl)oxy)hexylidene)amino)propanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of novel prodrugs of naproxen

  摘要：

  A series of novel prodrugs of naproxen has been synthesized. Naproxen (1) was reacted with thionyl chloride to yield acid chloride (2) which was further reacted with glucose to form the glucosyl naproxen (3). Tetra-acetate of glucosyl naproxen was prepared and finally reacted with different amino acids to yield the title compounds. These compounds were evaluated for analgesic, anti-inflammatory activities, and for possible GI toxicity. Compound 5b depicted most potent analgesic activity with percentage inhibition of 98.15%. Compound 5a was found to be most potent anti-inflammatory agent with 76% inhibition. Compound 5n was second most active analgesic (92.26%) and anti-inflammatory (73%) agent. In vitro hydrolysis pattern of synthesized prodrugs was studied in phosphate buffer of pH 7.4 and acetate buffers of pH 3.0, 4.0, and 5.0, respectively. Selected compounds were evaluated for their ulcerogenic potential and all the tested derivatives were significantly less irritating to gastric mucosa than the parent drug.

  DOI：

  10.1007/s00044-010-9364-8