(4S)-2-(3-Hydroxy-6-oxocyclohexa-2,4-dien-1-ylidene)-1,3-thiazolidine-4-carboxylic acid | 917955-23-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S)-2-(3-Hydroxy-6-oxocyclohexa-2,4-dien-1-ylidene)-1,3-thiazolidine-4-carboxylic acid
• 英文别名: (4S)-2-(2,5-dihydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid
• CAS: 917955-23-8
• 化学式: C₁₀H₉NO₄S
• 分子量: 239.252
• InChiKey: UZKPUFNAUXBOOI-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,5-二甲氧基苯甲腈 在 三溴化硼 、 碳酸氢钠 作用下， 以 甲醇 、 phosphate buffer 、 二氯甲烷 为溶剂， 反应 66.0h， 生成 (4S)-2-(3-Hydroxy-6-oxocyclohexa-2,4-dien-1-ylidene)-1,3-thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  The Design, Synthesis, and Evaluation of Organ-Specific Iron Chelators

  摘要：

  A series of iron chelators, three (S)-4,5-dihydro-2-(2-hydroxyphenyl)-4-methyl-4-thiazolecarboxylic acid (DADFT) and three (S)-4,5-dihydro-2-(2-hydroxyphenyl)-4-thiazolecarboxylic acid (DADMDFT) analogues are synthesized and assessed for their lipophilicity (log Papp), iron-clearing efficiency (ICE) in rodents and iron-loaded primates (Cebus apella), toxicity in rodents, and organ distribution in rodents. The results lead to a number of generalizations useful in chelator design strategies. In rodents, while log Papp is a good predictor of a chelator's ICE, chelator liver concentration is a better tool. In primates, log Papp is a good predictor of ICE, but only when comparing structurally very similar chelators. There is a profound difference in toxicity between the DADMDFT and DADFT series: DADMDFTs are less toxic. Within the DADFT family of ligands, the more lipophilic ligands are generally more toxic. Lipophilicity can have a profound effect on ligand organ distribution, and ligands can thus be targeted to organs compromised in iron overload disease, for example, the heart.

  DOI：

  10.1021/jm0608816