(4R)-2-(4-hydroxy-3-methoxyphenyl)thiazolidine-4-carboxylic acid | 933484-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (4R)-2-(4-hydroxy-3-methoxyphenyl)thiazolidine-4-carboxylic acid
• 英文别名: (4R)-2-(4-hydroxy-3-methoxyphenyl)-4-carboxy-1,3-thiazolidine；(2Ξ,4R)-2-(4-hydroxy-3-methoxy-phenyl)-thiazolidine-4-carboxylic acid；(2Ξ,4R)-2-(4-Hydroxy-3-methoxy-phenyl)-thiazolidin-4-carbonsaeure；(4R)-2-(4-hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid
• CAS: 933484-83-4
• 化学式: C₁₁H₁₃NO₄S
• 分子量: 255.295
• InChiKey: JWNFSTNMEBJXKG-BYDSUWOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-半胱氨酸盐酸盐无水物 、 香草醛 在 乙醇 、 potassium acetate 作用下， 生成 (4R)-2-(4-hydroxy-3-methoxyphenyl)thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  2-Substituted-thiazolidine-4-carboxylic Acids

  摘要：

  DOI：

  10.1021/ja01184a520
• 作为试剂：
  描述：

  二苯基硅烷 、 苯乙酮 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (4R)-2-(4-hydroxy-3-methoxyphenyl)thiazolidine-4-carboxylic acid 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以37%的产率得到(1-phenylvinyloxy)(diphenyl)silane
  参考文献：
  名称：

  Conformational analysis, spectral and catalytic properties of 1,3-thiazolidines, ligands for acetophenone hydrosilylation with diphenylsilane

  摘要：

  2-Aryl- and 2-furyl-4-carboxy-1,3-thiazolidines were synthesized. Their spectral properties were studied, and conformational analysis was performed. It was shown that they exist in solution as an equilibrium of neutral and zwitter-ion forms. The influence of the nature of substitutents and of their location in a benzene ring of thiazolidines as ligands of rhodium complexes on acetophenone hydrosilylation with diphenylsilane was examined. Thiazolidines containing donor substituents in the para-position of the benzene ring were found to be the most effective; maximal asymmetrical induction (55% ee) was reached in the presence of 2-(4-methoxyphenyl)-4-carboxy-1,3-thiazolidine.

  DOI：

  10.1134/s107036321010021x

文献信息

• Design, synthesis and biological evaluation of 2-(substituted phenyl)thiazolidine-4-carboxylic acid derivatives as novel tyrosinase inhibitors
  作者：Young Mi Ha、Yun Jung Park、Ji Yeon Lee、Daeui Park、Yeon Ja Choi、Eun Kyeong Lee、Ji Min Kim、Jin-Ah Kim、Ji Young Park、Hye Jin Lee、Hyung Ryong Moon、Hae Young Chung

  DOI：10.1016/j.biochi.2011.09.002

  日期：2012.2

  describe the design, synthesis and biological activities of 2-(substituted phenyl)thiazolidine-4-carboxylic acid derivatives as novel tyrosinase inhibitors. The target compounds 2a-2j were designed and synthesized from the structural characteristics of N-phenylthiourea, tyrosinase inhibitor and tyrosine, and l-DOPA, the natural substrates of tyrosinase. Among them, (2R/S,4R)-2-(2,4-dimethoxyphenyl)

  在这里，我们描述2-（取代的苯基）噻唑烷-4-羧酸衍生物作为新型酪氨酸酶抑制剂的设计，合成和生物学活性。根据N-苯基硫脲，酪氨酸酶抑制剂和酪氨酸的结构特征以及酪氨酸酶的天然底物1-DOPA的结构特征设计和合成目标化合物2a-2j。其中，（2R / S，4R）-2-（2,4-二甲氧基苯基）噻唑烷-4-羧酸（2g）在20μM蘑菇酪氨酸酶的1-DOPA氧化酶活性上产生最大的抑制作用达66.47％。酪氨酸酶抑制的动力学分析表明2g是竞争性抑制剂。我们预测了酪氨酸酶的三级结构，并模拟了蘑菇酪氨酸酶与2g的对接。这些结果表明2g与酪氨酸酶的结合亲和力高。还，2g有效抑制了用α-MSH处理的B16细胞中的酪氨酸酶活性并降低了黑色素水平。这些数据强烈表明2g可通过抑制酪氨酸酶活性来抑制黑色素的产生。