2-(4-Thiochroman-4-yl-phenoxy)-propionic acid ethyl ester | 1028281-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-Thiochroman-4-yl-phenoxy)-propionic acid ethyl ester
• 英文别名: ethyl 2-[4-(3,4-dihydro-2H-thiochromen-4-yl)phenoxy]propanoate
• CAS: 1028281-50-6
• 化学式: C₂₀H₂₂O₃S
• 分子量: 342.459
• InChiKey: JHTASQPFUSSCMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-Thiochroman-4-yl-phenoxy)-propionic acid ethyl ester 在 sodium hydroxide 、 正丁基锂 、 N-环己基异丙基胺 作用下， 以 乙醇 为溶剂， 反应 4.33h， 生成 Sodium; 3-(3-ethyl-phenyl)-2-methyl-2-(4-thiochroman-4-yl-phenoxy)-propionate
  参考文献：
  名称：

  Glucose Transport-Enhancing and Hypoglycemic Activity of 2-Methyl-2-phenoxy-3-phenylpropanoic Acids

  摘要：

  A series of 2-phenoxy-3-phenylpropanoic acids has been prepared which contains many potent hypoglycemic agents as demonstrated by assessing glucose lowering in ob/ob mice. Some compounds (32, 33, 59) normalize plasma glucose in this diabetic model at doses of approximately 1 mg/kg. The mechanism of action of these drugs may involve enhanced glucose transport, especially in fat cells, but the compounds do not stimulate GLUT4 translocation and do not increase the levels of GLUT1 or GLUT4 in vivo. Thus, these compounds may enhance the intrinsic activity of the glucose transporter GLUT1 or GLUT4. Some compounds also modestly decrease hepatocyte gluconeogenesis in vitro, but this is not likely to be a major contributor to the hypoglycemic effect observed in vivo. Likewise, a modest decrease in food consumption observed with some of these compounds was shown by a pair-feeding experiment not to be the primary cause of the hypoglycemia observed.

  DOI：

  10.1021/jm950364f
• 作为产物：
  描述：

  (4-溴苯氧基)叔丁基二甲基硅烷 在 Pd-BaSO₄ 盐酸 、 氢气 、 potassium carbonate 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~70.0 ℃ 、317.16 kPa 条件下， 反应 72.0h， 生成 2-(4-Thiochroman-4-yl-phenoxy)-propionic acid ethyl ester
  参考文献：
  名称：

  Glucose Transport-Enhancing and Hypoglycemic Activity of 2-Methyl-2-phenoxy-3-phenylpropanoic Acids

  摘要：

  A series of 2-phenoxy-3-phenylpropanoic acids has been prepared which contains many potent hypoglycemic agents as demonstrated by assessing glucose lowering in ob/ob mice. Some compounds (32, 33, 59) normalize plasma glucose in this diabetic model at doses of approximately 1 mg/kg. The mechanism of action of these drugs may involve enhanced glucose transport, especially in fat cells, but the compounds do not stimulate GLUT4 translocation and do not increase the levels of GLUT1 or GLUT4 in vivo. Thus, these compounds may enhance the intrinsic activity of the glucose transporter GLUT1 or GLUT4. Some compounds also modestly decrease hepatocyte gluconeogenesis in vitro, but this is not likely to be a major contributor to the hypoglycemic effect observed in vivo. Likewise, a modest decrease in food consumption observed with some of these compounds was shown by a pair-feeding experiment not to be the primary cause of the hypoglycemia observed.

  DOI：

  10.1021/jm950364f