(2R,3R)-3-((2-氨基-5-甲氧基苯基)硫基)-2-羟基-3-(4-甲氧基苯基)丙酸甲酯 | 100601-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (2R,3R)-3-((2-氨基-5-甲氧基苯基)硫基)-2-羟基-3-(4-甲氧基苯基)丙酸甲酯
• 英文名称: threo-2-hydroxy-3-<(2-amino-5-methoxyphenyl)thio>-3-(4-methoxyphenyl)propionic acid methyl ester
• 英文别名: methyl 3-(2-amino-5-methoxyphenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoate
• CAS: 100601-17-0；132618-96-3
• 化学式: C₁₈H₂₁NO₅S
• 分子量: 363.434
• InChiKey: VNGBTWUJSZDHDU-UHFFFAOYSA-N

物化性质

• 沸点：
  541.5±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  91.01
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  3-(4-甲氧基苯基)环氧乙烷-2-甲酸甲酯 、 2-氨基-5-甲氧基苯硫酚 以 甲苯 为溶剂， 反应 6.0h， 以63%的产率得到(2R,3R)-3-((2-氨基-5-甲氧基苯基)硫基)-2-羟基-3-(4-甲氧基苯基)丙酸甲酯
  参考文献：
  名称：

  Benzazepinone calcium channel blockers. 5. Effects on antihypertensive activity associated with N1 and aromatic substituents

  摘要：

  We have shown that the pyrrolidinylmethyl substituent on the lactam nitrogen (Nl) of benzazepinone and benzothiazepinone calcium channel blocking agents is resistant to metabolic deamination and generally increases the duration and potency of antihypertensive activity in spontaneously hypertensive rats (SHR) relative to (N,N-dimethylamino) ethyl analogs. Additionally, compounds possessing a substituent on the fused aromatic ring are more resistant to metabolic deacylation of the C3 hydroxy function, which may explain why aromatic substituents also frequently increase the potency and/or duration of antihypertensive activity. Our data also indicate the in antihypertensive activity associated with these structural modifications is independent of any effects of potency in vitro. Overall, we interpret these results to indicate that these structural modifications improve antihypertensive activity as a result of increased metabolic stability and, consequently, oral bioavailability.

  DOI：

  10.1021/jm00092a011