2-(4-chlorobenzyl)-2,3-dihydro-6-isopropyl-4H-benzopyran-2-carboxylic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-(4-chlorobenzyl)-2,3-dihydro-6-isopropyl-4H-benzopyran-2-carboxylic acid
• 英文别名: 2-[(4-Chlorophenyl)methyl]-6-propan-2-yl-3,4-dihydrochromene-2-carboxylic acid
• 化学式: C₂₀H₂₁ClO₃
• 分子量: 344.838
• InChiKey: PBYAZRIAJAWOAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(4-Chloro-phenyl)-2-(4-isopropyl-phenoxy)-propionic acid ethyl ester 在 palladium on activated charcoal 三乙基硅烷 、 sodium hydroxide 、 sodium tetrahydroborate 、 正丁基锂 、 三氟甲磺酸 、 N-环己基异丙基胺 、 氢气 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 4.83h， 生成 2-(4-chlorobenzyl)-2,3-dihydro-6-isopropyl-4H-benzopyran-2-carboxylic acid
  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

文献信息

• Glucose Transport-Enhancing and Hypoglycemic Activity of 2-Methyl-2-phenoxy-3-phenylpropanoic Acids
  作者：Reinhard Sarges、Richard F. Hank、James F. Blake、Jon Bordner、Donald L. Bussolotti、Diane M. Hargrove、Judith L. Treadway、E. Michael Gibbs

  DOI：10.1021/jm950364f

  日期：1996.1.1

  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.