8-(diethoxyphosphorylmethoxy)-4H-indeno[1,2-d][1,3]thiazol-2-amine | 911233-54-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 8-(diethoxyphosphorylmethoxy)-4H-indeno[1,2-d][1,3]thiazol-2-amine
• CAS: 911233-54-0
• 化学式: C₁₅H₁₉N₂O₄PS
• 分子量: 354.367
• InChiKey: NGVGTLYRGNGHNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-(diethoxyphosphorylmethoxy)-4H-indeno[1,2-d][1,3]thiazol-2-amine 在 亚硝酸特丁酯 、 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 以44%的产率得到
  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
• 作为产物：
  描述：

  2-Bromo-7-(diethoxyphosphorylmethoxy)-2,3-dihydroinden-1-one 、 硫脲 在 sodium acetate 作用下， 以 乙醇 为溶剂， 以46%的产率得到8-(diethoxyphosphorylmethoxy)-4H-indeno[1,2-d][1,3]thiazol-2-amine
  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

文献信息

• Synthesis, SAR, and X-ray structure of tricyclic compounds as potent FBPase inhibitors
  作者：Tomoharu Tsukada、Mizuki Takahashi、Toshiyasu Takemoto、Osamu Kanno、Takahiro Yamane、Sayako Kawamura、Takahide Nishi

  DOI：10.1016/j.bmcl.2009.08.081

  日期：2009.10

  With the aim of discovering a novel class of fructose-1,6-bisphosphatase (FBPase) inhibitors, a series of compounds based on tricyclic scaffolds was synthesized. Extensive SAR studies led to the finding of 8l with an IC50 value of 0.013 mu M against human FBPase. An X-ray crystallographic study revealed that 8l bound at AMP binding sites of human liver FBPase with hydrogen bonding interactions similar to AMP. (C) 2009 Elsevier Ltd. All rights reserved.