1,3,5-trimethylpyrrolo[3,2-d]pyrimidine-2,4(1H,3H)-dione | 55276-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 1,3,5-trimethylpyrrolo[3,2-d]pyrimidine-2,4(1H,3H)-dione
• 英文别名: caffeine；1,3,5-trimethyl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione；1,3,5-Trimethylpyrrolo<3,2-d>pyrimidin-2,4(1H,3H)-dion；1H-Pyrrolo(3,2-d)pyrimidine-2,4(3H,5H)-dione, 1,3,5-trimethyl-；1,3,5-trimethylpyrrolo[3,2-d]pyrimidine-2,4-dione
• CAS: 55276-30-7
• 化学式: C₉H₁₁N₃O₂
• 分子量: 193.205
• InChiKey: VJEONQKOZGKCAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3,5-trimethylpyrrolo[3,2-d]pyrimidine-2,4(1H,3H)-dione 在 硫酸 、 硝酸 作用下， 反应 1.5h， 以47%的产率得到1,3,5-trimethyl-6,7-dinitropyrrolo[3,2-d]pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  吡咯并[3,2-d]嘧啶-2,4-二酮的硝基衍生物：胺和基于其的新多核杂环的合成

  摘要：

  1,3-二甲基吡咯并[3,2- d ]嘧啶-2,4-二酮在不同条件下的硝化导致它们的6（7）-单-和6,7-二硝基衍生物的形成，还原为相应的胺。后者与α-和β-二羰基化合物以及邻醌反应生成许多新的多环杂芳族体系。

  DOI：

  10.1134/s1070428017100128
• 作为产物：
  描述：

  1,3,4-三甲基尿嘧啶 在 palladium on activated charcoal 硫酸 、 氢气 、 硝酸 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 1,3,5-trimethylpyrrolo[3,2-d]pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and Structure-Activity Relationships of Deazaxanthines: Analogs of Potent A1- and A2-Adenosine Receptor Antagonists

  摘要：

  A set of 22 9-deazaxanthines (pyrrolo[3,2-d]pyrimidine-2,4-diones) and three 7-deazaxanthines (pyrrolo[2,3-d] pyrimidine-2,4-diones) with various substituents in the 1-, 3-, 7- or 9-, and 8-positions was synthesized and investigated in A1 and A2a adenosine receptor binding assays at rat brain cortical membranes and rat brain striatal membranes, respectively. 9-Deazaxanthines showed structure-activity relationships that were similar to those of xanthines. They were about equipotent to the corresponding xanthines at A2a adenosine receptors. 9-Deazaxanthines were generally at least 2-3-fold more potent than xanthines at A1 receptors and therefore exhibited higher A1 selectivities compared to the xanthines. 1,3-Dimethyl-8-(2-naphthyl)-9-deazaxanthine (19e) showed high affinty (K-i = 26 nM) and selectivity for A1 adenosine receptors. A hydroxyl function at N7 of 9-deazaxanthines was unfavorable for A1 and A2a receptor binding. 7-Deazaxanthines were considerably less potent compared to xanthines and to 9-deazaxanthines at both receptor subtypes.

  DOI：

  10.1021/jm00036a019

文献信息

• Application of Host–Guest Complexation Method to Isolation of Natural Product
  作者：Mari Segawa、Koji Mori、Fumio Toda

  DOI：10.1246/cl.1988.1755

  日期：1988.10.5

  Application of host–guest complexation method to isolation of caffeine, nicotine, and cholesterol from tea and tabaco leaves, and gallstone, respectively, has been reported. Separations of strychnine and brucine, and sparteine and brucine by the same method were also reported.

  据报道，已采用主客体络合方法分别从茶叶和烟叶中分离咖啡因和尼古丁，以及从胆结石中分离胆固醇。此外，还报道了通过同样的方法分离马钱子碱和布鲁辛，以及刺檗碱和布鲁辛。
• 5-[(Pyren-9-ylmethyl)amino]isophthalic acid with nitrogen containing heterocycles: stacking, N–H⋯π interactions and photoluminescence
  作者：Jagajiban Sendh、Munendra Pal Singh、Jubaraj B. Baruah

  DOI：10.1039/d1ce01099a

  日期：——

  1 : 1 salt, namely a mono-protonated 4,4′-bipyridinium cation with [HL]−, was also analysed. The 4,4′-bipyridinium salt of the HL anion had the pyrene rings assembled as pairs and were arranged in a head-to-tail arrangement. It lacked intermolecular N–H⋯π interactions. It had unusual pyridine–pyridine R22(6) synthons formed by C–H⋯N hydrogen bonds. Among the cocrystals the caffeine cocrystal was weakly

  在芘衍生的二羧酸的共晶中，由伙伴分子引导的不同合成子、π-堆积和分子间 N-H⋯π 相互作用被证明。为此目的，二甲基甲酰胺的 1:1 溶剂化物和 1:1 与 6-苯基-1,3,5-三嗪-2,4-二胺 (PTDA)、4,6-二甲基嘧啶-2 共晶的自组装研究了-胺(DMPA)或咖啡因以及与吩嗪(Phen)的5-[(芘-9-基甲基)氨基]间苯二甲酸(H 2 L)的2:1共晶。比较了这些自组装体中芘环之间的 π 堆积。还评估了这些组件中不同的合成子和堆叠模式。DMF 溶剂化物以及 H 2的 PTDA 共晶L 具有平行的 π 叠芘环，每个芘环都以头对尾的方式组织（其中头是芘的取代端，尾是芘的另一端）。两个组件都具有分子间 N–H⋯π 相互作用。吩嗪在吩嗪共晶中的两个间苯二甲酸单元之间黯然失色。它具有 η 3 -N–H⋯π 分子内相互作用。共晶与 DMPA 的组装具有以平行方式组织的成对堆叠的芘单元。这些单元通过分子间
• Pharmaceutical Cocrystals of Niclosamide
  作者：Palash Sanphui、S. Sudalai Kumar、Ashwini Nangia

  DOI：10.1021/cg300784v

  日期：2012.9.5

  Niclosamide (NCL) is an anthelmintic BCS class II drug of low solubility and high permeability. Pharmaceutical cocrystals of NCL were prepared with GRAS molecules, such as caffeine (CAF), urea (URE), p-aminobenzoic acid (PABA), theophylline (THPH), nicotinamide (NCT), and isonicotinamide (INA), to improve drug solubility. Neat grinding, wet granulation, and slow evaporation methods were successful to make niclosamide cocrystals. All new crystalline forms were characterized by X-ray diffraction, differential scanning calorimetry, and IR-Raman spectroscopy to confirm their purity and homogeneity. X-ray crystal structures provided details of hydrogen bonding, molecular packing, and drug...coformer interactions. The intermolecular O-H center dot center dot center dot O hydrogen bond from the hydroxyl donor to the carbonyl acceptor in the niclosamide crystal structure was replaced by an acceptor atom of the coformer in cocrystal structures. Cocrystals with nicotinamide and isonicotinamide were characterized by C-13 ss-NMR spectroscopy because their single crystals could not be obtained. All cocrystals, except NCL-PABA, showed a faster powder dissolution rate than the reference active pharmaceutical ingredient (API). Niclosamide theophylline acetonitrile solvate showed the highest solubility (6 times compared to the API) among all the crystalline forms. NCL-THPH cocrystals showed comparably good dissolution (5 times faster than the drug) up to 90 min. The solubility advantage of the cocrystal was diminished by transformation to insoluble niclosamide monohydrate within 1 h of the dissolution experiment in 40% i-PrOH-water. Equilibrium solubility experiments showed that all cocrystals as well as the pure API transformed to NCL monohydrate within 24 h in 40% i-PrOH-water slurry medium. Among the cocrystals studied, NCL-NCT and NCL-INA exhibited better stability under accelerated humidity conditions (75% RH, 40 degrees C), but they did not have the same solubility advantage as the fast dissolving species NCL THPH.
• SMALL-MOLECULE POVIDONE ANALOGS IN COAMORPHOUS PHARMACEUTICAL PHASES
  申请人：ISP INVESTMENTS LLC

  公开号：US20200188408A1

  公开（公告）日：2020-06-18

  An amorphous dispersion comprises bis(vinylcaprolactam) and an active pharmaceutical ingredient.