2-chloromethyl-5,6-dimethyl-thieno[2,3-d]pyrimidin-4-ylamine | 877964-04-0

• 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: 2-chloromethyl-5,6-dimethyl-thieno[2,3-d]pyrimidin-4-ylamine
• 英文别名: 2-(Chloromethyl)-5,6-dimethylthieno[2,3-d]pyrimidin-4-amine
• CAS: 877964-04-0
• 化学式: C₉H₁₀ClN₃S
• mdl: MFCD07762675
• 分子量: 227.718
• InChiKey: JBYRXDIWCGCYCN-UHFFFAOYSA-N

物化性质

• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N-((diethylamino)(phenyl)methylenecarbamothioyl)benzamide 、 2-chloromethyl-5,6-dimethyl-thieno[2,3-d]pyrimidin-4-ylamine 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以54%的产率得到N-[5-(4-amino-5,6-dimethylthieno[2,3-d]pyrimidin-2-yl)-4-phenylthiazol-2-yl]benzamide
  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
• 作为产物：
  描述：

  2-氨基-3-腈基-4,5-二甲基噻吩 、 氯乙腈 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-chloromethyl-5,6-dimethyl-thieno[2,3-d]pyrimidin-4-ylamine
  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

• An efficient one-pot synthesis of functionally diverse 2-aminothiazoles from isothiocyanates, amidines/guanidines and halomethylenes
  作者：Hitesh B. Jalani、Amit N. Pandya、Dhaivat H. Pandya、Jayesh A. Sharma、V. Sudarsanam、Kamala K. Vasu

  DOI：10.1016/j.tetlet.2013.07.122

  日期：2013.9

  efficient one-pot method for the synthesis of 2-aminothiazoles using simple starting materials like isothiocyanates, amidines/guanidines and various halomethylenes is reported. The synthesis of 2-aminothiazoles involves reactions such as nucleophilic addition, S-alkylation and intramolecular nucleophilic substitution in which amines departs as the leaving group.

  报道了一种有效的一锅法，该方法使用诸如异硫氰酸酯，am /胍和各种卤代亚甲基之类的简单原料来合成2-氨基噻唑。2-氨基噻唑的合成涉及诸如亲核加成，S-烷基化和分子内亲核取代的反应，其中胺作为离去基团离开。
• 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.