agomelatine methyl 4-hydroxybenzoate adduct | 1366181-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: agomelatine methyl 4-hydroxybenzoate adduct
• 英文别名: N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide;methyl 4-hydroxybenzoate
• CAS: 1366181-85-2
• 化学式: C₈H₈O₃*C₁₅H₁₇NO₂
• 分子量: 395.455
• InChiKey: WBSRLUOEFUQIHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对羟基苯甲酸甲酯 、 阿戈美拉汀 以98%的产率得到agomelatine methyl 4-hydroxybenzoate adduct
  参考文献：
  名称：

  Improving the Solubility of Agomelatine via Cocrystals

  摘要：

  Four cocrystals of agomelatine with urea (1), glycolic acid (2), isonicotinamide (3), and methyl 4-hydroxybenzoate (4) in 1:1 stoichiometry were successfully synthesized via six kinds of synthons. The structures of 1-4 were determined by the single crystal X-ray diffraction, in which 1-3 form two-dimensional hydrogen bonded frameworks between agomelatine and coformers, while 4 displays a one-dimensional chain structure. The results of differential scanning calorimetry measurements indicate that the melting points of 1-3 are between those of agomelatine and coformers, while the melting point of 4 is below those of agomelatine and coformer. After the formations of cocrystals, the solubility of agomelatine is much improved, and the solubility values of 1-4 in phosphate buffer of pH 6.8 are approximately 2.2, 2.9, 4.7, and 3.5 times as large as that of agomelatine Form II, and 1.6, 2.1, 3.4, and 2.5 times as large as that of agomelatine Form I. The solids of 1-4 can keep their crystalline forms in phosphate buffer of pH 6.8 for 3.5, 2.0, 6.0, and 15.0 h, respectively.

  DOI：

  10.1021/cg201423q