5-[(6-methyl-2-morpholin-4-ylpyrimidin-4-yl)oxymethyl]-3H-1,3,4-oxadiazole-2-thione | 347849-36-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-[(6-methyl-2-morpholin-4-ylpyrimidin-4-yl)oxymethyl]-3H-1,3,4-oxadiazole-2-thione
• CAS: 347849-36-9
• 化学式: C₁₂H₁₅N₅O₃S
• 分子量: 309.349
• InChiKey: NUXAACNJOAIOPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  吗啉 、 聚合甲醛 、 5-[(6-methyl-2-morpholin-4-ylpyrimidin-4-yl)oxymethyl]-3H-1,3,4-oxadiazole-2-thione 以 乙醇 为溶剂， 反应 1.0h， 以74%的产率得到
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of 5-(6-methyl-2-substituted 4-pyrimidinyloxymethyl)-1,3,4-oxadiazole-2-thiones and their 3-morpholinomethyl derivatives

  摘要：

  The synthesis of 5-(6-methyl-2-substituted 4-pyrimidinyloxymethyl)-2,3-dihydro-1,3,4-oxadiazole-2-thiones and their 3-morpholinomethyl derivatives and the results of anti-inflammatory activity in vivo are described. Most of the tested compounds exhibited anti-inflammatory activity and some of them were more active than acetylsalicylic acid.

  DOI：

  10.1016/s0014-827x(02)00022-8
• 作为产物：
  描述：

  (6-Methyl-2-morpholin-4-yl-pyrimidin-4-yloxy)-acetic acid methyl ester 在 一水合肼 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 13.0h， 生成 5-[(6-methyl-2-morpholin-4-ylpyrimidin-4-yl)oxymethyl]-3H-1,3,4-oxadiazole-2-thione
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of 5-(6-methyl-2-substituted 4-pyrimidinyloxymethyl)-1,3,4-oxadiazole-2-thiones and their 3-morpholinomethyl derivatives

  摘要：

  The synthesis of 5-(6-methyl-2-substituted 4-pyrimidinyloxymethyl)-2,3-dihydro-1,3,4-oxadiazole-2-thiones and their 3-morpholinomethyl derivatives and the results of anti-inflammatory activity in vivo are described. Most of the tested compounds exhibited anti-inflammatory activity and some of them were more active than acetylsalicylic acid.

  DOI：

  10.1016/s0014-827x(02)00022-8

文献信息

• Synthesis and histone deacetylases inhibitory activity of pyrimidine‐based 1,3,4‐oxadiazoles
  作者：V. Jakubkiene、I. Labalaukyte、M. Schweipert、A. Zubriene、F.‐J. Meyer‐Almes、D. Matulis、S. Tumkevicius

  DOI：10.1002/jhet.4867

  日期：2024.9

  promising therapeutic target for the treatment of various diseases. Here, the synthesis of a series of pyrimidine-based 1,3,4-oxadiazoles, in which the oxadiazole scaffold is attached to the pyrimidine ring via a methyleneoxy spacer, is described and their HDAC inhibitory activity studied. The target compounds were synthesized by sequence of reactions involving O-alkylation of 2-(methylthio)pyrimidin-4(3H)-ones

  组蛋白脱乙酰酶 (HDAC) 正在被探索作为治疗各种疾病的有前景的治疗靶点。在此，描述了一系列基于嘧啶的 1,3,4-恶二唑的合成，其中恶二唑支架通过亚甲氧基间隔基连接到嘧啶环，并研究了它们的 HDAC 抑制活性。通过2-(甲硫基)嘧啶-4(3 H )-酮与2-溴乙酸乙酯的O-烷基化反应，然后氧化2-甲硫基，置换所得2-甲磺酰基，合成了目标化合物将所得的(2-氨基取代嘧啶-4-基氧基)乙酸乙酯肼解得到相应的酰肼，再用O-乙基黄原酸乙酯或羰基二咪唑处理环化生成1,3,4-恶二唑-相应地，2(3 H )-硫酮和1,3,4-恶二唑-2(3 H )-酮。此外，两个1,3,4-恶二唑-2(3 H )-硫酮通过与甲醛和吗啉的曼尼希反应转化为( N 3)-吗啉代甲基衍生物。中间体和目标化合物的产率从中等到优秀。合成的化合物通过1 H 和13 C NMR 谱和 HRMS 数据进行表征，通过 TLC 控制其纯度。测试了合成的基于嘧啶的