ethyl 4-hydroxy-3,5-diiodo-α-methylphenylacetate | 138460-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: ethyl 4-hydroxy-3,5-diiodo-α-methylphenylacetate
• 英文别名: Ethyl 2-(4-hydroxy-3,5-diiodophenyl)propanoate
• CAS: 138460-08-9
• 化学式: C₁₁H₁₂I₂O₃
• 分子量: 446.023
• InChiKey: SWCZPVPBRPKBNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-3,5-diiodo-α-methylphenylacetate 在 ammonium hydroxide 、 氢碘酸 、 碘 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 28.0h， 生成 α-methyl-3,5,3'-triiodothyroacetic acid
  参考文献：
  名称：

  .alpha.-Methylated analogs of triiodothyroalkanoic acids: synthesis and biological activity

  摘要：

  Three novel thyroid hormone analogues: alpha-methyl-3,5,3'-triiodothyroacetic acid, alpha-methyl-3,5,3'-triiodothyropropionic acid, and alpha-methyl-3,5,3',5'-tetraiodothyropropionic acid were synthesized. The hepatic thyroid receptor affinity of these analogues was compared to that other available thyroid analogues. The ability of these compounds to increase the activity of two hepatic enzymes and to lower blood cholesterol was compared to that of L-triiodothyronine. alpha-Methyl-3,5,3'-triiodothyroacetic acid was shown to have less nuclear binding affinity, less enzyme inducing ability, but more blood cholesterol lowering ability than triiodothyroacetic acid. alpha-Methyl-3,5,3',5'-tetraiodothyropropionic acid showed less nuclear binding affinity and less enzyme-inducing activity than alpha-methyl-3,5,3'-triiodothyropropionic acid.

  DOI：

  10.1021/jm00081a017
• 作为产物：
  描述：

  2-(4-羟基苯)丙酸 在 碘 、 对甲苯磺酸 、 potassium iodide 作用下， 生成 ethyl 4-hydroxy-3,5-diiodo-α-methylphenylacetate
  参考文献：
  名称：

  .alpha.-Methylated analogs of triiodothyroalkanoic acids: synthesis and biological activity

  摘要：

  Three novel thyroid hormone analogues: alpha-methyl-3,5,3'-triiodothyroacetic acid, alpha-methyl-3,5,3'-triiodothyropropionic acid, and alpha-methyl-3,5,3',5'-tetraiodothyropropionic acid were synthesized. The hepatic thyroid receptor affinity of these analogues was compared to that other available thyroid analogues. The ability of these compounds to increase the activity of two hepatic enzymes and to lower blood cholesterol was compared to that of L-triiodothyronine. alpha-Methyl-3,5,3'-triiodothyroacetic acid was shown to have less nuclear binding affinity, less enzyme inducing ability, but more blood cholesterol lowering ability than triiodothyroacetic acid. alpha-Methyl-3,5,3',5'-tetraiodothyropropionic acid showed less nuclear binding affinity and less enzyme-inducing activity than alpha-methyl-3,5,3'-triiodothyropropionic acid.

  DOI：

  10.1021/jm00081a017