5-乙酰基-6-氨基-1,3-二甲基嘧啶-2,4-二酮 | 32970-32-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-乙酰基-6-氨基-1,3-二甲基嘧啶-2,4-二酮
• 中文别名: 5-乙酰基-6-胺基-1,3-二甲基尿嘧啶
• 英文名称: 5-acetyl-6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 1,3-Dimethyl-5-acetyl-6-aminouracil；Dimethyl-1,3-amino-4-acetyl-5-uracil；5-acetyl-6-amino-1,3-dimethyl-1H-pyrimidine-2,4-dione；5-Acetyl-6-amino-1,3-dimethyl-1H-pyrimidin-2,4-dion；5-acetyl-6-amino-1,3-dimethyluracil；5-acetyl-6-amino-1,3-dimethylpyrimidine-2,4-dione
• CAS: 32970-32-4
• 化学式: C₈H₁₁N₃O₃
• mdl: MFCD00717269
• 分子量: 197.194
• InChiKey: UIIVTPCAYOUSLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  83.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  5-乙酰基-6-氨基-1,3-二甲基嘧啶-2,4-二酮 在 碘苯二乙酸 、 lithium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以82%的产率得到3,5,7-trimethylisoxazolo<3,4-d>pyrimidine-4,6(5H,7H)-dione
  参考文献：
  名称：

  Iodobenzene Diacetate–Promoted N–N and N–O Bond Formation for Pyrazolo- and Isoxazolopyrimidine Syntheses

  摘要：

  Pyrazolo[3,4-d]pyrimidine-4,6-dione derivatives were efficiently synthesized via the intramolecular N-N bond coupling of 5-iminomethyl-6-aminouracil derivatives using iodobenzene diacetate. The oxidative coupling was also applied to the analogous N-O bond formation producing isoxazolo[3,4-d]primidine-4,6-dione derivatives.

  DOI：

  10.3987/com-08-s(d)34
• 作为产物：
  描述：

  1,3-二甲基-6-氨基脲嘧啶 、 乙酰氯 以68%的产率得到
  参考文献：
  名称：

  BERNIER J.-L.; LEFEBVRE A.; HENICHART J.-P.; HOUSSIN R.; LESPAGNOL CH., BULL. SOC. CHIM. FRANCE , 1976, NO 3-4, PART. 2, 616-620

  摘要：

  DOI：

文献信息

• Selective Inhibitors of a Human Prolyl Hydroxylase (OGFOD1) Involved in Ribosomal Decoding
  作者：Cyrille C. Thinnes、Christopher T. Lohans、Martine I. Abboud、Tzu‐Lan Yeh、Anthony Tumber、Radosław P. Nowak、Martin Attwood、Matthew E. Cockman、Udo Oppermann、Christoph Loenarz、Christopher J. Schofield

  DOI：10.1002/chem.201804790

  日期：2019.2.6

  Human prolyl hydroxylases are involved in the modification of transcription factors, procollagen, and ribosomal proteins, and are current medicinal chemistry targets. To date, there are few reports on inhibitors selective for the different types of prolyl hydroxylases. We report a structurally informed template-based strategy for the development of inhibitors selective for the human ribosomal prolyl

  人脯氨酰羟化酶参与转录因子，前胶原蛋白和核糖体蛋白的修饰，并且是当前的药物化学靶标。迄今为止，很少有关于对不同类型的脯氨酰羟化酶具有选择性的抑制剂的报道。我们报告了结构选择性的抑制剂为人类核糖体脯氨酰羟化酶OGFOD1选择性抑制剂发展的基于模板的策略。这些抑制剂未针对其他测试的人类加氧酶，包括结构相似的低氧诱导转录因子脯氨酰羟化酶PHD2。
• 5-substituted pyrido[2,3-d]pyrimidine-2,4-diones
  申请人：Nippon Zoki Pharmaceutical Co., Ltd.

  公开号：US04808587A1

  公开（公告）日：1989-02-28

  The present invention relates to a novel pyrido[2,3-d]pyrimidine derivative having the formula (I): ##STR1## wherein each of R.sub.1 and R.sub.2, which may be the same or different, is a lower alkyl group; and each of R.sub.3 and R.sub.4, which may be the same or different, is hydrogen, halogen, hydroxy, nitro, amino, hydroxyamino, hydrazino, azido, a lower alkenylamino group or a lower alkylamino group which may optionally have hydroxy; and pharmaceutically acceptable salt thereof. These compounds are useful as anti-allergic agents, for example, for the treatment of bronchial asthma, urticaria, allergic rhinitis, allergic dermatoses or allergic conjunctivitis.

  本发明涉及一种具有以下式（I）的新型吡啶并[2,3-d]嘧啶衍生物：其中R.sub.1和R.sub.2中的每一个（可以相同也可以不同）是较低的烷基基团；R.sub.3和R.sub.4中的每一个（可以相同也可以不同）是氢、卤素、羟基、硝基、氨基、羟胺基、叠氮基、叠氮基、较低烯基氨基基团或较低烷基氨基基团，该基团可能具有羟基；以及其药学上可接受的盐。这些化合物可用作抗过敏剂，例如用于治疗支气管哮喘、荨麻疹、过敏性鼻炎、过敏性皮肤病或过敏性结膜炎。
• Pyrido[2,3-d]pyrimidine derivatives
  申请人：NIPPON ZOKI PHARMACEUTICAL CO. LTD.

  公开号：EP0243311A2

  公开（公告）日：1987-10-28

  The present invention relates to a novel pyrido[2,3-d]pyrimidine derivative having the formula (1): wherein each of R, and R2, which may be the same or different, is a lower alkyl group; and each of R3 and R4, which may be the same or different, is hydrogen, halogen, hydroxy, nitro, amino, hydroxyamino, hydrazino, azido, a lower alkenylamino group or a lower alkylamino group which may optionally be substituted by hydroxy; and pharmaceutically acceptable salt thereof. These compounds are useful as anti-allergic agents, for example, for the treatment of bronchial asthma, urticaria, allergic rhinitis, allergic dermatoses or allergic conjunctivitis.

  本发明涉及一种具有式(1)的新型吡啶并[2,3-d]嘧啶衍生物： 其中R和R2（可以相同或不同）各自为低级烷基；R3和R4（可以相同或不同）各自为氢、卤素、羟基、硝基、氨基、羟基氨基、肼基、叠氮基、低级烯氨基或可任选被羟基取代的低级烷氨基；及其药学上可接受的盐。这些化合物可用作抗过敏剂，例如用于治疗支气管哮喘、荨麻疹、过敏性鼻炎、过敏性皮肤病或过敏性结膜炎。
• Synthesis and pharmacology of pyrido[2,3-d]pyrimidinediones bearing polar substituents as adenosine receptor antagonists
  作者：Jacek Bulicz、Daniela C.G. Bertarelli、Dieter Baumert、Friederike Fülle、Christa E. Müller、Dieter Heber

  DOI：10.1016/j.bmc.2005.12.008

  日期：2006.4

  Amino-substituted pyrido[2,3-d]pyrimidinediones have previously been found to bind to adenosine A(1) and A(2A) receptors in micromolar concentrations. The present study was aimed at studying the structure-activity relationships of this class of compounds in more detail. Most of the investigated compounds were provided with polar substituents. such as ethoxycarbonyl groups and basic amino functions, in order to improve their water-solubility. The compounds were synthesized starting from 6-amino-1,3-dimethyfuracil via different reaction sequences involving (cyano)acetylation, Vilsmeier formylation, or reaction with diethyl ethoxymethylemalonate (EMME). The most potent and selective compound of the present series was 6-carbethoxy-1,2,3,4-tetrahydro-1.3-dimethyl-5-(2-naphthylmethyl) aminopyrido[2,3-d]pyrimidine-2,4-dione (11c) with a K-i value of 5 nM at rat and 25 nM at human A, receptors. The compound was more than 60-fold selective versus A(3) and more than 300-fold selective versus A2A receptors. It showed all over 300-fold improvement with respect to the lead compound. In GTP gamma S binding studies at membranes of Chinese hamster ovary cells recombinantly expressing the human adenosine A, receptor, 11c behaved as an antagonist with inverse agonistic activity. A regioisomer of 11c, 6-carbethoxy-1,2,3,4-tetrahydro-1,3-dimethyl-7-(2-naphthylmethyl)aminopyrido[2,3-d]pyrimidine-2,4-dione (7a) in which the 2-naphthylmethylamino substituent at position 5 of 11c was moved to the 7-position, was a relatively potent (K-i = 226 nM) and selective (> 20-fold) A(3) ligand. In the series of compounds lacking an electron-withdrawing ethoxycarbonyl or cyano substituent in the 6-position, compounds with high affinity for adenosine A(2A) receptors were identified. Such as 1,2,3,4-tetrahydro-1,3-dimethyl-5-(1-naphthyl)aminopyrido[2,3-d]pyrimidine-2,4-dioile 16b (K-i human A(2A) = 81.3 nM, K-i human A(1) = 153 nM, and K-i human A(3) > 10,000 nM). (c) 2006 Elsevier Ltd. All rights reserved.
• Pfleiderer; Strauss, Justus Liebigs Annalen der Chemie, 1958, vol. 612, p. 173,176,177
  作者：Pfleiderer、Strauss

  DOI：——

  日期：——