N-[5-(4-amino-5,6,7,8-tetrahydrobenzo[4,5]-thieno[2,3-d]pyrimidin-2-yl)-4-phenylthiazol-2-yl]-4-methylbenzamide | 1443221-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: N-[5-(4-amino-5,6,7,8-tetrahydrobenzo[4,5]-thieno[2,3-d]pyrimidin-2-yl)-4-phenylthiazol-2-yl]-4-methylbenzamide
• 英文别名: N-[5-(4-amino-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)-4-phenyl-1,3-thiazol-2-yl]-4-methylbenzamide
• CAS: 1443221-51-9
• 化学式: C₂₇H₂₃N₅OS₂
• 分子量: 497.645
• InChiKey: SEVDLEUJLNRULN-UHFFFAOYSA-N

物化性质

• 熔点：
  >310 °C
• 密度：
  1.393±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N,N-diethylbenzamidine 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 51.0h， 生成 N-[5-(4-amino-5,6,7,8-tetrahydrobenzo[4,5]-thieno[2,3-d]pyrimidin-2-yl)-4-phenylthiazol-2-yl]-4-methylbenzamide
  参考文献：
  名称：

  New insight into adenosine receptors selectivity derived from a novel series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamides and furamides

  摘要：

  A series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamide and furamide analogues were investigated in radioligand binding studies at adenosine receptor subtypes with an aim to obtain potent and selective adenosine receptor ligands. Benzamide and furamide linked to thiazole was found to be crucial for high adenosine receptor affinity. The most potent compound indentified in this study was 5d with low nanomolar affinity for all four adenosine receptor subtypes. Compounds 5a and 5g showed moderate selectivity for A(2A) adenosine receptors. Molecular docking versus all four human adenosine receptors combined with membrane molecular dynamics studies were performed to rationalise the peculiar selectivity profile of 5d antagonist. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.020

文献信息

• New insight into adenosine receptors selectivity derived from a novel series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamides and furamides
  作者：Gajanan S. Inamdar、Amit N. Pandya、Hardik M. Thakar、Vasudevan Sudarsanam、Sonja Kachler、Davide Sabbadin、Stefano Moro、Karl-Norbert Klotz、Kamala K. Vasu

  DOI：10.1016/j.ejmech.2013.03.020

  日期：2013.5

  A series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamide and furamide analogues were investigated in radioligand binding studies at adenosine receptor subtypes with an aim to obtain potent and selective adenosine receptor ligands. Benzamide and furamide linked to thiazole was found to be crucial for high adenosine receptor affinity. The most potent compound indentified in this study was 5d with low nanomolar affinity for all four adenosine receptor subtypes. Compounds 5a and 5g showed moderate selectivity for A(2A) adenosine receptors. Molecular docking versus all four human adenosine receptors combined with membrane molecular dynamics studies were performed to rationalise the peculiar selectivity profile of 5d antagonist. (C) 2013 Elsevier Masson SAS. All rights reserved.