5-(1,3-Benzoxazol-2-yl)benzene-1,3-diol | 1004983-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(1,3-Benzoxazol-2-yl)benzene-1,3-diol
• CAS: 1004983-88-3
• 化学式: C₁₃H₉NO₃
• 分子量: 227.219
• InChiKey: YKTWLILRERAQCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(3,5-二甲氧基苯基)苯并[d]恶唑 在 三溴化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 18.0h， 以70%的产率得到5-(1,3-Benzoxazol-2-yl)benzene-1,3-diol
  参考文献：
  名称：

  Biochemical and Structural Evaluation of Highly Selective 2-Arylbenzoxazole-Based Transthyretin Amyloidogenesis Inhibitors

  摘要：

  To develop potent transthyretin (TTR) amyloidogenesis inhibitors that also display high binding selectivity in blood, it proves useful to systematically optimize each of the three substructural elements that comprise a typical inhibitor: the two aryl rings and the linker joining them. In the first study, described herein, structural modifications to one aryl ring were evaluated by screening a library of 2-arylbenzoxazoles bearing thyroid hormone-like aryl substituents on the 2-aryl ring. Several potent and highly selective amyloidogenesis inhibitors were identified that exhibit minimal thyroid hormone nuclear receptor and COX-1 binding. High resolution crystal structures (1.3-1.5 angstrom) of three inhibitors (2f, 4f, and 4d) in complex with TTR were obtained to characterize their binding orientation. Collectively, the results demonstrate that thyroid hormone-like substitution patterns on one aryl ring lead to potent and highly selective TTR amyloidogenesis inhibitors that lack undesirable thyroid hormone receptor or COX-1 binding.

  DOI：

  10.1021/jm0708735