6-[(4-methyl-1-piperazinyl)carbonyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

• 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: 6-[(4-methyl-1-piperazinyl)carbonyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
• 英文别名: 6-(4-methylpiperazine-1-carbonyl)-5H-thiazolo[3,2-a]pyrimidin-5-one；6-(4-Methylpiperazine-1-carbonyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one
• 化学式: C₁₂H₁₄N₄O₂S
• 分子量: 278.335
• InChiKey: ODKKORHKVJRUPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氧代-5H-噻唑并[3,2-a]嘧啶-6-甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.83h， 生成 6-[(4-methyl-1-piperazinyl)carbonyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
  参考文献：
  名称：

  新型功能化咪唑并[2,1- b ]噻唑和噻唑并[3,2- a ]嘧啶的合成

  摘要：

  5-Oxo-5 H- [1,3]噻唑并[3,2 - a ]嘧啶-6-羧酸（4）和6-甲基咪唑并[2,1 - b ]噻唑-5-羧酸（17）通过与草酰氯和作为催化剂的N，N-二甲基甲酰胺的反应，使胺与胺6a-i反应成伯和仲酰胺衍生物7-14和19-22。由化合物24制备N，N′-二取代的脲26、27和咪唑并[2，1- b ]噻唑的全氢咪唑并[ 1，5- c ]噻唑29衍生物。通过化合物的核磁共振分析 由图29可知，存在由C7'a的手性中心引起的旋光性和C5N6 '键的旋转受限引起的构象异构性这两种立体异构体的存在。

  DOI：

  10.1002/jhet.5570370115

文献信息

• Allosteric Inhibition of a Mammalian Lectin
  作者：Jonas Aretz、Upendra R. Anumala、Felix F. Fuchsberger、Narges Molavi、Nandor Ziebart、Hengxi Zhang、Marc Nazaré、Christoph Rademacher

  DOI：10.1021/jacs.8b08644

  日期：2018.11.7

  Glycan-binding proteins are key components of central physiological and cellular processes such as self-/non-self-recognition, cellular tissue homing, and protein homeostasis. Herein, C-type lectins are a diverse protein family that play important roles in the immune system, rendering them attractive drug targets. To evaluate C-type lectin receptors as target proteins for small-molecule effectors, chemical probes are required, which are, however, still lacking. To overcome the supposedly poor druggability of C-type lectin receptors and to identify starting points for chemical probe development, we screened murine langerin using H-1 and F-19 NMR against a library of 871 drug-like fragments. Subsequently, hits were validated by surface plasmon resonance and enzyme-linked lectin assay. Using structure activity relationship studies and chemical synthesis, we identified thiazolopyrimidine derivatives with double-digit micromolar activity that displayed langerin selectivity. Based on H-10-N-15 HSQC NMR and competitive binding and inhibition experiments, we demonstrate that thiazolopyrimidines allosterically inhibit langerin. To the best of our knowledge, this is the first report of drug-like allosteric inhibitors of a mammalian lectin.
• Synthesis of new functionalized imidazo[2,1-b]thiazoles and thiazolo[3,2-a]pyrimidines
  作者：Lucija Peterlin-Mašič、Mateja Malešič、Matej Breznik、AleŠ Krbavčič

  DOI：10.1002/jhet.5570370115

  日期：2000.1

  and 6-methylimidazo[2,1-b]thiazole-5-carboxylic acid (17) were reacted with amines 6a-i by the reaction with oxalyl chloride and N, N-di methyl-formamide as a catalyst into primary and secondary amide derivatives 7-14 and 19-22. From compound 24 N,N'-disubstituted ureas 26, 27 and perhydroimidazo[1,5-c]thiazole 29 derivatives of imidazo[2,1-b]thiazole were prepared. By nmr analysis of compound 29, the

  5-Oxo-5 H- [1,3]噻唑并[3,2 - a ]嘧啶-6-羧酸（4）和6-甲基咪唑并[2,1 - b ]噻唑-5-羧酸（17）通过与草酰氯和作为催化剂的N，N-二甲基甲酰胺的反应，使胺与胺6a-i反应成伯和仲酰胺衍生物7-14和19-22。由化合物24制备N，N′-二取代的脲26、27和咪唑并[2，1- b ]噻唑的全氢咪唑并[ 1，5- c ]噻唑29衍生物。通过化合物的核磁共振分析 由图29可知，存在由C7'a的手性中心引起的旋光性和C5N6 '键的旋转受限引起的构象异构性这两种立体异构体的存在。