3,6-dimethyl-5-nitrouracil | 27889-92-5

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3,6-dimethyl-5-nitrouracil
• 英文别名: 3,6-dimethyl-5-nitro-1H-pyrimidine-2,4-dione；3,6-Dimethyl-5-nitro-1H-pyrimidin-2,4-dion；3,6-dimethyl-5-nitro-1,3-dihydropyrimidine-2,4-dione；3,6-Dimethyl-5-nitropyrimidine-2,4(1H,3H)-dione；3,6-dimethyl-5-nitro-1H-pyrimidine-2,4-dione
• CAS: 27889-92-5
• 化学式: C₆H₇N₃O₄
• 分子量: 185.139
• InChiKey: TWTDBGBBAHKLBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-dimethyl-5-nitrouracil 在 哌啶 、 亚磷酸三乙酯 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 3-Methyl-6-phenyl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-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
• 作为产物：
  描述：

  6-((E)-2-Dimethylamino-vinyl)-3-methyl-5-nitro-1H-pyrimidine-2,4-dione 在 sodium hydroxide 作用下， 以95%的产率得到3,6-dimethyl-5-nitrouracil
  参考文献：
  名称：

  Hirota, Kosaku; Abe, Yoshio; Asao, Tetsuji, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 985 - 990

  摘要：

  DOI：

文献信息

• [EN] PYRROLO[3,2-D]PYRIMIDINE-2,4(3H,5H)-DIONE DERIVATIVES<br/>[FR] DÉRIVÉS DE PYRROLO[3,2-D]PYRIMIDINE-2,4(3H,5H)-DIONE
  申请人：HYDRA BIOSCIENCES INC

  公开号：WO2016023831A1

  公开（公告）日：2016-02-18

  This invention relates to novel Pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione derivatives of Formula (I), and their use as TRPC5 modulators, pharmaceutical compositions containing the same, and methods of using the same as agents for the treatment of TRPC5 receptor mediated disorders or conditions. R1, R2, R3 R4 and R5 have meanings given in the description.

  本发明涉及一种新型的Pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-二酮衍生物，其化学式为（I），以及它们作为TRPC5调节剂的用途，含有这些化合物的药物组合物，以及将其用作治疗TRPC5受体介导的疾病或症状的药物的方法。R1、R2、R3、R4和R5的含义见描述。
• A2B adenosine receptor antagonists
  申请人：Kalla Rao

  公开号：US20050119287A1

  公开（公告）日：2005-06-02

  Disclosed are novel compounds that are A 2B adenosine receptor antagonists having the following structure: wherein R 1 and R 2 are independently chosen from hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, and optionally substituted heteroaryl, and R 4 is an optionally substituted heteroaryl moiety. The compounds of the invention are useful for treating various disease states, including asthma, chronic obstructive pulmonary disorder, pulmonary inflammation, emphysema, diabetic disorders, inflammatory gastrointestinal tract disorders, immunological/inflammatory disorders, cardiovascular diseases, neurological disorders, and diseases related to angiogenesis.

  本发明涉及一种新的化合物，该化合物是A2B腺苷受体拮抗剂，其结构如下：其中R1和R2独立地选择自氢、可选择性取代的烷基、可选择性取代的环烷基、可选择性取代的芳基和可选择性取代的杂环芳基，而R4是可选择性取代的杂环芳基基团。本发明的化合物可用于治疗各种疾病状态，包括哮喘、慢性阻塞性肺疾病、肺部炎症、肺气肿、糖尿病性疾病、炎症性胃肠道疾病、免疫/炎症性疾病、心血管疾病、神经系统疾病和与血管生成相关的疾病。
• Discovery of a New Class of Uracil Derivatives as Potential Mixed Lineage Kinase Domain-like Protein (MLKL) Inhibitors
  作者：Bo Cui、Bo Yan、Kang Wang、Lin Li、She Chen、Zhiyuan Zhang

  DOI：10.1021/acs.jmedchem.2c00548

  日期：2022.10.13

  programmed cell death. Mixed lineage kinase domain-like protein (MLKL) is the necroptosis executor, and it is involved in various diseases such as tissue damage and neurodegeneration-related diseases. Here, we report the development of novel MLKL inhibitors with a uracil nucleus through scaffold morphing from our previously reported xanthine MLKL inhibitor TC13172. After a rational structure–activity relationship

  坏死性凋亡是程序性细胞死亡的一种形式。混合谱系激酶域样蛋白（MLKL）是坏死性凋亡的执行者，它参与多种疾病，如组织损伤和神经退行性疾病相关疾病。在这里，我们报告了通过支架变形从我们之前报道的黄嘌呤 MLKL 抑制剂 TC13172 开发出具有尿嘧啶核的新型 MLKL 抑制剂。经过合理的构效关系研究，我们得到了高效化合物56和66。机理研究表明，这些化合物部分抑制了 MLKL 寡聚化，并显着抑制了 MLKL 易位至膜。与 TC13172、56和66相比具有不同的作用方式，重要的是，它们与谷胱甘肽的反应速率低 150 倍以上。这种潜在脱靶效应和细胞毒性的降低使该系列成为进一步开发 MLKL 相关疾病治疗药物的有吸引力的起点。
• Lehmann, Justus Liebigs Annalen der Chemie, 1889, vol. 253, p. 84
  作者：Lehmann

  DOI：——

  日期：——
• Henkel, Justus Liebigs Annalen der Chemie, 1911, vol. 378, p. 182
  作者：Henkel

  DOI：——

  日期：——