2-(3-hydroxypyridin-2-yl)thiazole-4-carboxylic acid | 115299-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-hydroxypyridin-2-yl)thiazole-4-carboxylic acid
• 英文别名: aeruginoic acid；2-(3-hydroxy-pyridin-2-yl)-4-thiazolecarboxylic acid；2-(3-hydroxy-2-pyridyl)-4-thiazolecarboxylic acid；2-(3-hydroxypyridin-2-yl)-1,3-thiazole-4-carboxylic acid
• CAS: 115299-12-2
• 化学式: C₉H₆N₂O₃S
• 分子量: 222.224
• InChiKey: PJNAJDFLPQURFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-氨基四氮唑 、 2-(3-hydroxypyridin-2-yl)thiazole-4-carboxylic acid 在 CDI 、 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以54%的产率得到2-(3-hydroxy-pyridin-2-yl)-N-(1H-tetrazole-5-yl)-4-thiazolecarboxamide
  参考文献：
  名称：

  N-tetrazolyl thiazolecarboxyamide derivatives and their use

  摘要：

  该化合物的结构式为：##STR1## 其中A是一个C.sub.1-6烷基基团，一个芳基团，未取代或取代，取代基包括至少一个羟基、烷氧基、芳基-(C.sub.1-6)烷氧基、C.sub.1-6烷基羰氧基、卤代-(C.sub.1-6)烷基、卤素、硝基和氨基，或者包含至少一个氧、氮和硫异原子的5-或6-成员杂环基团，或者由上述定义的杂环基团和苯核组成的缩合杂环基团，这两个杂环基团未取代或取代，取代基包括至少一个羟基、C.sub.1-6烷基和卤素，R是氢或C.sub.1-6烷基基团，或其药学上可接受的盐，用作抗过敏药物。

  公开号：

  US04879295A1
• 作为产物：
  描述：

  methyl 2-(3-hydroxypyridin-2-yl)thiazole-4-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以85%的产率得到2-(3-hydroxypyridin-2-yl)thiazole-4-carboxylic acid
  参考文献：
  名称：

  Desazadesmethyldesferrithiocin Analogues as Orally Effective Iron Chelators

  摘要：

  Further structure-activity studies of desferrithiocin analogues are carried out. (S)-desazadesmethyldesferrithiocin, 2-(2-hydroxyphenyl)-Delta(2)-thiazoline-4(S)-carboxylic acid, serves as the principal framework in the current paper. Desazadesmethyldesferrithiocin can be structurally altered with facility, and data are already available on its iron-clearing properties and toxicity parameters. Four different kinds of structural modifications of this framework are undertaken: introduction of hydroxy, carboxy, or methoxy groups on the aromatic ring; alteration of the thiazoline ring; increasing the distance between the ligand donor atoms; and benz-fusion of the aromatic rings. The structural modifications described are shown to have a tremendous imp act on both the iron clearance and toxicity profiles of the desazadesmethyldesferrithiocin molecule. All of the compounds are assessed in a bile-duct-cannulated rodent model to determine iron clearance efficiency. Ligands which demonstrate an efficiency of greater than 2% are carried forward to the iron-overloaded primate for iron-clearing measurements. Ligands with efficiencies greater than 3% in the primate are then evaluated in a formal toxicity study in rodents. On the basis of the results of the present work, 2-(2,4-dihydroxyphenyl)-Delta(2)-thiazoline-4(S)-carboxylic acid is a promising candidate for clinical evaluation.

  DOI：

  10.1021/jm980340j

文献信息

• N-tetrazolyl thiazolecarboxamide derivatives and their use
  申请人：SAWAI PHARMACEUTICAL CO., LTD.

  公开号：EP0262873B1

  公开（公告）日：1991-08-21
• YOSHINAGA, JUNJI;SHOYAKI, TAKESHI;KAKITA, TAKAO;OZEKI, HIROMI;SUGIMOTO, N+
  作者：YOSHINAGA, JUNJI、SHOYAKI, TAKESHI、KAKITA, TAKAO、OZEKI, HIROMI、SUGIMOTO, N+

  DOI：——

  日期：——
• US4879295A
  申请人：——

  公开号：US4879295A

  公开（公告）日：1989-11-07