2-(3,5-dimethyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one | 180090-38-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(3,5-dimethyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one
• 英文别名: 2-(4-Hydroxy-3,5-dimethylphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one
• CAS: 180090-38-4
• 化学式: C₁₄H₁₉NO₃S
• 分子量: 281.376
• InChiKey: HMLRJHBYBRDSSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,5-dimethyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one 在 氯化亚砜 、 sodium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3-(3-{[2-(benzo[1,3]dioxol-5-yloxy)-ethyl]-methyl-amino}-propyl)-2-(4-hydroxy-3,5-dimethyl-phenyl)-thiazolidin-4-one
  参考文献：
  名称：

  Novel Calcium Antagonists with Both Calcium Overload Inhibition and Antioxidant Activity. 2. Structure−Activity Relationships of Thiazolidinone Derivatives

  摘要：

  CP-060 (1), 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-[N-methyl-N-[2-[3,4-(methylenedioxy)phenoxy]ethyl]amino]propyl]-1,3-thiazolidin-4-one, is a novel type of Ca2+ antagonist possessing both Ca2+ overload inhibition and antioxidant activity. The structure-activity relationships for this series of compounds were studied by synthesizing the analogues and evaluating these three kinds of activity. Ca2+ antagonistic activity was largely determined by the lipophilicity of the phenyl group at the 2-position and the length of the alkyl chains. As for-the antioxidant activity, it was demonstrated that the phenolic hydroxyl group is an essential structural element. Compounds with potent activity were! evaluated for their effect on the coronary blood flow in vivo. Among these compounds, compound 1 was shown to be the most potent. Furthermore, the enantiomers of 1 were resolved by high-performance liquid chromatography with a chiral column. Compound (-)-1 showed about 10 times higher Ca2+ antagonistic activity than (+)-1, though both enarrtiomers had similar potency in Ca2+ overload inhibition and antioxidant activity. An X-ray crystal structure determination of (-)-1 hydrogen fumarate identified (-)-1 as having S configuration at the 2-position.

  DOI：

  10.1021/jm9900927
• 作为产物：
  描述：

  3,5-二甲基-4-羟基苯甲醛 以 苯 为溶剂， 反应 3.5h， 生成 2-(3,5-dimethyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Novel Calcium Antagonists with Both Calcium Overload Inhibition and Antioxidant Activity. 2. Structure−Activity Relationships of Thiazolidinone Derivatives

  摘要：

  CP-060 (1), 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-[N-methyl-N-[2-[3,4-(methylenedioxy)phenoxy]ethyl]amino]propyl]-1,3-thiazolidin-4-one, is a novel type of Ca2+ antagonist possessing both Ca2+ overload inhibition and antioxidant activity. The structure-activity relationships for this series of compounds were studied by synthesizing the analogues and evaluating these three kinds of activity. Ca2+ antagonistic activity was largely determined by the lipophilicity of the phenyl group at the 2-position and the length of the alkyl chains. As for-the antioxidant activity, it was demonstrated that the phenolic hydroxyl group is an essential structural element. Compounds with potent activity were! evaluated for their effect on the coronary blood flow in vivo. Among these compounds, compound 1 was shown to be the most potent. Furthermore, the enantiomers of 1 were resolved by high-performance liquid chromatography with a chiral column. Compound (-)-1 showed about 10 times higher Ca2+ antagonistic activity than (+)-1, though both enarrtiomers had similar potency in Ca2+ overload inhibition and antioxidant activity. An X-ray crystal structure determination of (-)-1 hydrogen fumarate identified (-)-1 as having S configuration at the 2-position.

  DOI：

  10.1021/jm9900927