5-氨基-1,3-二甲基嘧啶-2,4(1H,3H)-二酮 | 49738-24-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-氨基-1,3-二甲基嘧啶-2,4(1H,3H)-二酮
• 英文名称: 1,3-dimethyl-5-aminouracil
• 英文别名: 5-amino-1,3-dimethyluracil；5-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione；5-amino-1,3-dimethylpyrimidine-2,4-dione
• CAS: 49738-24-1
• 化学式: C₆H₉N₃O₂
• mdl: MFCD09388770
• 分子量: 155.156
• InChiKey: KPADHLBAZFIMTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  5-氨基-1,3-二甲基嘧啶-2,4(1H,3H)-二酮 在 硫酸 、 硝酸 、 铁粉 、 sodium hydride 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 2.25h， 生成 咖啡因
  参考文献：
  名称：

  A Novel Method of Caffeine Synthesis from Uracil

  摘要：

  An inexpensive and novel method of caffeine synthesis starting from uracil in six simple steps is described. Uracil 1 is first converted to I, 3-dimethyluracil 2, followed by nitration, reduction, and cyclization to theophylline and finally methylation of theophylline forms caffeine.

  DOI：

  10.1081/scc-120023986
• 作为产物：
  描述：

  1,3-二甲基脲嘧啶 在 盐酸 、 硫酸 、 硝酸 、 铁粉 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 5-氨基-1,3-二甲基嘧啶-2,4(1H,3H)-二酮
  参考文献：
  名称：

  A Novel Method of Caffeine Synthesis from Uracil

  摘要：

  An inexpensive and novel method of caffeine synthesis starting from uracil in six simple steps is described. Uracil 1 is first converted to I, 3-dimethyluracil 2, followed by nitration, reduction, and cyclization to theophylline and finally methylation of theophylline forms caffeine.

  DOI：

  10.1081/scc-120023986

文献信息

• [EN] FUSED PYRIMIDINE-DIONE DERIVATIVES AS TRPA1 MODULATORS<br/>[FR] DÉRIVÉS DE PYRIMIDINEDIONES FUSIONNÉS UTILISÉS COMME MODULATEURS DES RÉCEPTEURS TRPA1
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2010109287A1

  公开（公告）日：2010-09-30

  The invention described herein relates to novel fused pyrimidinediones derivatives of formula (I) which are TRPA (Transient Receptor Potential subfamily A) modulators. In particular, compounds described herein are useful for treating or preventing diseases, conditions and/or disorders modulated by TRPAl (Transient Receptor Potential subfamily A, member 1). This invention also provides processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders modulated by TRPAl. Formula (I)

  本发明描述的是一类新颖的杂合吡啶二酮衍生物，其化学公式为（I），这些衍生物是TRPA（瞬时受体电位亚家族A）的调节剂。特别是，本文所述的化合物对于治疗或预防由TRPA1（瞬时受体电位亚家族A成员1）调控的疾病、状况和/或失调是有用的。本发明还提供了制备所述化合物、它们合成中使用的中间体、药物组合物以及治疗或预防由TRPA1调控的疾病、状况和/或失调的方法。公式（I）
• A green one-pot three-component synthesis of spirooxindoles under conventional heating conditions or microwave irradiation by using Fe3O4@SiO2-imid-PMAn magnetic porous nanospheres as a recyclable catalyst
  作者：Mohsen Esmaeilpour、Jaber Javidi、Masoumeh Divar

  DOI：10.1016/j.jmmm.2016.09.020

  日期：2017.2

  Abstract An efficient, green and environmentally procedure for the synthesis of spirooxindole derivatives has been developed by a one-pot three-component reaction of isatin derivatives, activated methylene, and 1,3-dicarbonyl compounds in the presence of Fe3O4@SiO2-imid-PMAn magnetic nanocatalyst under conventional heating conditions in water or microwave irradiation under solvent-free conditions.

  摘要 通过靛红衍生物、活化亚甲基和 1,3-二羰基化合物在 Fe3O4@SiO2-imid- 存在下的一锅三组分反应，开发了一种高效、绿色和环保的合成螺吲哚衍生物的方法。 PMAn磁性纳米催化剂，在水中常规加热条件下或在无溶剂条件下微波辐射。将常规加热条件下的反应与微波辅助反应进行了比较。建议的方法提供了几个优点，例如高产率、反应时间短、操作简单、反应更清洁、没有任何繁琐的后处理或纯化以及易于回收和磁场可重复使用催化剂。此外，在水介质中具有优异的催化性能和易于制备，催化剂的热稳定性和分离性使其成为一种良好的多相体系，是其他多相催化剂的有用替代品。该催化剂可以很容易地通过磁场回收并重复使用六个连续的反应循环而不会显着损失活性。此外，通过扫描电子显微镜 (SEM)、动态光散射 (DLS) 和电感耦合等离子体 (ICP) 研究了反应循环后 Fe3O4@SiO2-imid-PMAn 的形貌、粒径分布和纳米
• Green sonosynthesis of pyridopyrimidines using heterogeneous Pd‐containing catalysts anchored on a hybrid organic–inorganic surface of <scp>SBA</scp> ‐15
  作者：Atefeh Bakhtiari、Javad Safaei‐Ghomi、Raheleh Teymuri

  DOI：10.1002/jccs.202100082

  日期：2021.9

  A novel functionalized Santa barbara amorphous (SBA)-15 mesoporous silica has been prepared as a catalyst and characterized using X-ray diffraction spectroscopy, Fourier-transform infrared spectroscopy, field-emission scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, X-ray photoelectron spectroscopy, temperature programmed desorption, N2 adsorption

  制备了一种新型官能化圣巴巴拉无定形 (SBA)-15 介孔二氧化硅作为催化剂，并使用 X 射线衍射光谱、傅里叶变换红外光谱、场发射扫描电子显微镜、透射电子显微镜、能量色散 X-射线光谱、X 射线光电子能谱、程序升温脱附、N 2吸附分析和差示热重分析 (TGA)。已通过合成多种多官能化吡啶并嘧啶来研究催化剂的产率。这种方法提供了几个优点，包括在短时间内高产率、催化剂的可重复使用性、低催化剂负载和温和的反应条件。
• [EN] IMIDAZOPYRROLIDINONE COMPOUNDS<br/>[FR] COMPOSÉS IMIDAZOPYRROLIDINONE
  申请人：NOVARTIS AG

  公开号：WO2013111105A1

  公开（公告）日：2013-08-01

  The invention relates to compounds of formula (I): (I) as described herein, pharmaceutical preparations comprising such compounds, uses and methods of use for such compounds in the treatment of a disorder or a disease mediated by the activity of MDM2 and/or MDM4, and combinations comprising such compounds.

  这项发明涉及式(I)的化合物：(I)如本文所述，包括这种化合物的药物制剂，以及在治疗由MDM2和/或MDM4活性介导的疾病或疾病中使用这种化合物的用途和方法，以及包含这种化合物的组合物。
• Effect of the 6-Methyl Group on Peroxyl Radical Trapping by 5-Hydroxyand 5-Amino- Derivatives of 1,3-Dimethyluracil
  作者：Stanislav Grabovskiy、Arcadiy Antipin、Yulia Grabovskaya、Nadezhda Andriayshina、Oksana Akchurina、Natalie Kabal'nova

  DOI：10.2174/1570178614666161121123024

  日期：2017.2.13

  Background: Many synthetic and natural uracil derivatives have biological activity. Furthermore, many of these derivatives have pro- and antioxidant properties, but the mechanism of these processes is far from being understood. Methods: Oxygen-uptake kinetics and computational methods (CBS-QB3, M062X/MG3S and SMDM05/ MG3S) were combined to study the reaction of peroxyl radicals with five organic-soluble derivatives: 5-amino- and 5-hydroxy-1,3-dimethyluracil, 5-amino- and 5-hydroxy-1,3,6-trimethyluracil, and 5-hydroxy-1,3-dimethyl-6-phenyluracil in chlorobenzene. Results: The studied uracil derivatives should be classified as inhibitors of medium reactivity kin = (1-10) × 10-4 M-1 s-1. The methyl group in the 6-position of the pyrimidine ring increases the rate constant of the reaction with peroxyl radicals by 3-4 times and the stoichiometric coefficient of inhibition. The calculation of the reaction barrier heights at the SMD-M05/MG3S level of theory for the hydrogen abstraction is in good agreement with experimental data. Conclusion: 1,3-Dimethyl-5-aminouracil is transformed by the addition of a methyl group at the 6-position into a favic-like pyrimidine, while the 5-hydroxy derivative becomes a more effective antioxidant. The bound dissociation energy (O-H or N-H) and the IP for the reactivity forecasting of uracil derivatives were used, but it was found that this methodology did not lead to good correlation between experimental and theoretical results. The SMD-M05/MG3S method provided the most accurate calculations of the reaction barrier heights for hydrogen abstraction from uracil derivatives by peroxyl radical.

  背景：许多合成和天然的尿嘧啶衍生物具有生物活性。此外，这些衍生物中的许多具有促进氧化和抗氧化特性，但其作用机制远未被理解。 方法：结合氧摄取动力学和计算方法（CBS-QB3、M062X/MG3S 和 SMDM05/MG3S）研究了过氧自由基与五种有机可溶性衍生物的反应：5-氨基和5-羟基-1,3-二甲基尿嘧啶、5-氨基和5-羟基-1,3,6-三甲基尿嘧啶，以及5-羟基-1,3-二甲基-6-苯基尿嘧啶在氯苯中的反应。 结果：所研究的尿嘧啶衍生物应归类为中等反应活性抑制剂，反应速率常数kin = (1-10) × 10-4 M-1 s-1。嘧啶环的6位甲基增加了与过氧自由基反应的速率常数3-4倍，并增加了抑制的化学计量系数。在SMD-M05/MG3S理论水平上对氢抽提反应势垒高度的计算与实验数据吻合良好。 结论：1,3-二甲基-5-氨基尿嘧啶通过在6位添加一个甲基，转化为类似favic的嘧啶，而5-羟基衍生物则成为更有效的抗氧化剂。使用了结合解离能（O-H或N-H）和IP来进行尿嘧啶衍生物反应性的预测，但发现这种方法并未导致实验和理论结果之间的良好相关性。SMD-M05/MG3S方法为过氧自由基从尿嘧啶衍生物中抽提氢的反应提供了最准确的势垒高度计算。