2-氨基-6-羟基-5-苯基-4(3H)-嘧啶酮 | 154146-07-3

• 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: 2-氨基-6-羟基-5-苯基-4(3H)-嘧啶酮
• 英文名称: 2-amino-5-phenylpyrimidine-4,6-diol
• 英文别名: 2-amino-4-hydroxy-5-phenyl-1H-pyrimidin-6-one
• CAS: 154146-07-3
• 化学式: C₁₀H₉N₃O₂
• 分子量: 203.2
• InChiKey: HPPMTXLIFATOQB-UHFFFAOYSA-N

物化性质

• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 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：

  2-氨基-6-羟基-5-苯基-4(3H)-嘧啶酮 在 盐酸 、 水 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.0h， 生成 4,6-dichloro-5-phenylpyrimidin-2-amine
  参考文献：
  名称：

  5-Substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4,6-dichloropyrimidines: synthesis and inhibitory effects on immune-activated nitric oxide production

  摘要：

  A series of 5-substituted 2-amino-4,6-dihydroxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, has been developed to convert the 2-amino-4,6-dihydroxypyrimidine analogs to novel 5-substituted 2-amino-4,6-dichloropyrimidines in high yields. Pilot screening for biological properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irrespective of the substituent at the 5 position, 2-amino-4,6-dichloropyrimidines inhibited immune-activated NO production. The most effective was 5-fluoro-2-amino-4,6-dichloropyrimidine with an IC ₅₀ of 2 µM (higher activity than the most potent reference compound) while the IC ₅₀s of other derivatives were within the range of 9-36 µM. The 2-amino-4,6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells. The Mechanism of action remains to be elucidated.

  DOI：

  10.1007/s00044-014-1018-9
• 作为产物：
  描述：

  2-azido-6-hydroxy-5-phenylpyrimidin-4(1H)-one 在 10percent P/C 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 8.0h， 以85%的产率得到2-氨基-6-羟基-5-苯基-4(3H)-嘧啶酮
  参考文献：
  名称：

  合成和反应的四唑并[1,5-α]嘧啶†往最‡

  摘要：

  在三乙胺的存在下，“魔术丙二酸酯”（双2,4,6-三氯苯基丙二酸酯，1）与5-氨基四唑（2）反应生成铵盐3。用强酸处理3后，得到化合物4a-d，其为异构的四唑并嘧啶（A）和2-叠氮基嘧啶（B）的混合物。的反应4D通过开环和脱羧的卤化四唑衍生物与溴或磺酰氯引线5或7，分别。吡啶中乙酸酐对3d的作用可生成两性离子四酸衍生物10。

  DOI：

  10.1002/jhet.5570300516

文献信息

• [EN] PYRIMIDINE COMPOUNDS INHIBITING THE FORMATION OF NITRIC OXIDE AND PROSTAGLANDIN E2, METHOD OF PRODUCTION THEREOF AND USE THEREOF<br/>[FR] COMPOSÉS DE PYRIMIDINE INHIBANT LA FORMATION D'OXYDE NITRIQUE ET PROSTAGLANDINE E2, LEUR PROCÉDÉ DE PRODUCTION ET LEUR UTILISATION
  申请人：USTAV ORGANICKE CHEMIE A BIOCHEMIE AKADEMIE VED CR V V I

  公开号：WO2012116666A1

  公开（公告）日：2012-09-07

  The invention provides pyrimidine compounds of general formula (I), which reduce simultaneously the production of nitric oxide (NO) and prostaglandin E2 (PGE2). They have no negative effect on the viability of cells in concentrations decreasing the production of these factors by up to 50%; they are not cytotoxic. Furthermore, a method of preparation of the pyrimidine compounds of general formula (I), carrying 2-formamido group, a pharmaceutical composition comprising the substituted pyrimidine compounds according to the invention, and the use of these compounds for the treatment of inflammatory and cancer diseases are provided.˙

  该发明提供了一般式(I)的嘧啶化合物，可以同时减少一氧化氮（NO）和前列腺素E2（PGE2）的产生。它们在降低这些因子产生达到50%的浓度下对细胞的存活性没有负面影响；它们不具有细胞毒性。此外，还提供了一种制备一般式(I)的带有2-甲酰胺基团的嘧啶化合物的方法，一种包括根据该发明的取代嘧啶化合物的药物组合物，以及利用这些化合物治疗炎症和癌症疾病的方法。
• PYRIMIDINE COMPOUNDS INHIBITING THE FORMATION OF NITRIC OXIDE AND PROSTAGLANDIN E2, METHOD OF PRODUCTION THEREOF AND USE THEREOF
  申请人：Ustav Organicke Chemie a Biochemie Akademie Ved CR, v.v.i.

  公开号：US20130324566A1

  公开（公告）日：2013-12-05

  The invention provides pyrimidine compounds of general formula (I), which reduce simultaneously the production of nitric oxide (NO) and prostaglandin E2 (PGE2). They have no negative effect on the viability of cells in concentrations decreasing the production of these factors by up to 50%; they are not cytotoxic. Furthermore, a method of preparation of the pyrimidine compounds of general formula (I), carrying 2-formamido group, a pharmaceutical composition comprising the substituted pyrimidine compounds according to the invention, and the use of these compounds for the treatment of inflammatory and cancer diseases are provided.

  本发明提供了一种通式（I）的嘧啶化合物，它们能同时减少一氧化氮（NO）和前列腺素E2（PGE2）的产生。它们在浓度减少这些因子的产生高达50％时，对细胞的生存能力没有负面影响，也不具有细胞毒性。此外，本发明还提供了一种制备带有2-甲酰胺基团的嘧啶化合物的方法，以及包含根据本发明所述的取代嘧啶化合物的制药组合物，以及使用这些化合物治疗炎症和癌症疾病的方法。
• Cascade Wolff Rearrangement and Double <i>N</i>‐Acylation: A Cyclization of <i>α</i>‐Diazoketones with 2‐aminopyridines or 3‐aminopyrazoles to Synthesize Fused Pyrimidinediones
  作者：Jun‐Jie Ren、Jia‐Xin Zhou、Yanqin Song、An‐Xin Zhang、Lu‐Xin Zhao、Zun‐Yuan Zhao、Yan‐Ping Zhu、Wei Zhu

  DOI：10.1002/adsc.202300773

  日期：2023.12.5

  A cascade Wolff rearrangement and double N-acylation reaction has been developed for the synthesis of fused pyrimidinediones in one-pot under air. These reactions were performed with α-diazoketones and 2-aminopyridines or 3-aminopyrazoles under catalyst- and additive-free conditions. The protocol avoided traditional purification procedures, such as organic solvent extraction and column chromatography

  开发了级联 Wolff 重排和双N -酰化反应，用于在空气下一锅法合成稠合嘧啶二酮。这些反应是用α-重氮酮和2-氨基吡啶或3-氨基吡唑在无催化剂和添加剂的条件下进行的。该方案避免了传统的纯化程序，例如有机溶剂萃取和柱色谱。生物活性分子的合成和克级实验证明了该反应的潜在应用。
• US8883798B2
  申请人：——

  公开号：US8883798B2

  公开（公告）日：2014-11-11
• 5-Substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4,6-dichloropyrimidines: synthesis and inhibitory effects on immune-activated nitric oxide production
  作者：Petr Jansa、Antonín Holý、Martin Dračínský、Viktor Kolman、Zlatko Janeba、Petra Kostecká、Eva Kmoníčková、Zdeněk Zídek

  DOI：10.1007/s00044-014-1018-9

  日期：2014.10

  A series of 5-substituted 2-amino-4,6-dihydroxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, has been developed to convert the 2-amino-4,6-dihydroxypyrimidine analogs to novel 5-substituted 2-amino-4,6-dichloropyrimidines in high yields. Pilot screening for biological properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irrespective of the substituent at the 5 position, 2-amino-4,6-dichloropyrimidines inhibited immune-activated NO production. The most effective was 5-fluoro-2-amino-4,6-dichloropyrimidine with an IC ₅₀ of 2 µM (higher activity than the most potent reference compound) while the IC ₅₀s of other derivatives were within the range of 9-36 µM. The 2-amino-4,6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells. The Mechanism of action remains to be elucidated.