(30a)-[(7-pyrimidin-5-yl-8H-indeno[1,2-d][1,3]thiazol-4-yl)oxy]methylphosphonic acid | 911232-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (30a)-[(7-pyrimidin-5-yl-8H-indeno[1,2-d][1,3]thiazol-4-yl)oxy]methylphosphonic acid
• 英文别名: (30b)-[(7-pyrimidin-5-yl-8H-indeno[1,2-d][1,3]thiazol-4-yl)oxy]methylphosphonic acid；[(7-pyrimidin-5-yl-8H-indeno[1,2-d][1,3]thiazol-4-yl)oxy]methylphosphonic acid；(7-(pyrimidin-5-yl)-8H-indeno[1,2-d]thiazol-4-yloxy)methylphosphonic acid；(5-pyrimidin-5-yl-4H-indeno[1,2-d][1,3]thiazol-8-yl)oxymethylphosphonic acid
• CAS: 911232-42-3
• 化学式: C₁₅H₁₂N₃O₄PS
• 分子量: 361.318
• InChiKey: PRMBOZWFZWHTPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  [(7-pyrimidin-5-yl-8H-indeno[1,2-d][1,3]thiazol-4-yl)oxy]methylphosphonic acid diethyl ester 在 三甲基溴硅烷 、 水 作用下， 以 二氯甲烷 为溶剂， 生成 (30a)-[(7-pyrimidin-5-yl-8H-indeno[1,2-d][1,3]thiazol-4-yl)oxy]methylphosphonic acid
  参考文献：
  名称：

  Structure-based drug design of tricyclic 8H-indeno[1,2-d][1,3]thiazoles as potent FBPase inhibitors

  摘要：

  With the goal of improving metabolic stability and further enhancing FBPase inhibitory activity, a series of tricyclic 8H-indeno[1,2-d][1,3]thiazoles was designed and synthesized with the aid of structure-based drug design. Extensive SAR studies led to the discovery of 19a with an IC50 value of 1 nM against human FBPase. X-ray crystallographic studies revealed that high affinity of 19a was due to the hydrophobic interaction arising from better shape complementarity and to the hydrogen bonding network involving the side chain on the tricyclic scaffold. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.056