2-amino-5-phenyl-3H-pyrimidin-4-one | 23948-24-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-amino-5-phenyl-3H-pyrimidin-4-one
• 英文别名: 2-Amino-5-phenyl-3H-pyrimidin-4-on；5-phenylisocytosine；2-amino-5-phenyl-1H-pyrimidin-6-one
• CAS: 23948-24-5
• 化学式: C₁₀H₉N₃O
• 分子量: 187.201
• InChiKey: BKXQDGXBCUTRBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  244-245 °C
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 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：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-5-phenyl-3H-pyrimidin-4-one 在 硝酸 、 溶剂黄146 作用下， 生成 5-(4-nitro-phenyl)-pyrimidine-2,4-diyldiamine
  参考文献：
  名称：

  US2624731

  摘要：

  公开号：
• 作为产物：
  描述：

  苯乙酸乙酯 在 乙醚 、 sodium 、 甲酸乙酯 作用下， 生成 2-amino-5-phenyl-3H-pyrimidin-4-one
  参考文献：
  名称：

  2,4-Diaminopyrimidines as Antimalarials. III. 5-Aryl Derivatives

  摘要：

  DOI：

  10.1021/ja01152a060

文献信息

• Direct synthesis of 5- and 6-substituted 2-aminopyrimidines as potential non-natural nucleobase analogues
  作者：K. Radhakrishnan、Namita Sharma、Lal Mohan Kundu

  DOI：10.1039/c4ra00249k

  日期：——

  A series of 2-aminopyrimidine derivatives, substituted at 5- and 6-positions, were synthesized. The reaction was carried out in a single step by treatment of the corresponding β-ketoester or β-aldehydoester with guanidine hydrochloride in the presence of K2CO3, in a microwave-assisted method without the requirement of solvent. A unique 1 : 1 co-crystal structure was obtained which shows that a 6-p

  合成了一系列5-和6-位取代的2-氨基嘧啶衍生物。该反应通过在K 2 CO 3存在下用盐酸胍处理相应的β-酮酸酯或β-醛二酸酯来一步进行。，不需要溶剂的微波辅助方法。获得独特的1：1共晶体结构，其显示6-苯基-2-氨基嘧啶酮与胞嘧啶形成强的核碱基对，涉及三个氢键。发现该碱基对与天然鸟嘌呤：胞嘧啶（G：C）一样强，表明合成衍生物的潜在应用。此外，我们还报告了第二个共晶体，该晶体以5：1的比例包含5-异丙基-6-甲基-2-氨基嘧啶酮和胞嘧啶，这也显示出很强的碱基配对特性。
• Discovery of thiazolyl-phthalazinone acetamides as potent glucose uptake activators via high-throughput screening
  作者：Madhavi Agrawal、Prashant Kharkar、Sonali Moghe、Tushar Mahajan、Vaishali Deka、Chandni Thakkar、Amrutha Nair、Chirag Mehta、Julie Bose、Asha Kulkarni-Almeida、Dilip Bhedi、Ram A. Vishwakarma

  DOI：10.1016/j.bmcl.2013.07.067

  日期：2013.10

  With the aim to discover orally active small molecules that stimulate glucose uptake, high throughput screening of a library of 5000 drug-like compounds was conducted in differentiated skeletal muscle cells in presence of insulin. N-Substituted phthalazinone acetamide was identified as a potential glucose uptake modulator. Several novel derivatives were synthesized to establish structure activity relationships. Identified lead thiazolyl-phthalazinone acetamide (7114863) increased glucose uptake (EC50 of 0.07 +/- 0.02 mu M) in differentiated skeletal muscle cells in presence of insulin. Furthermore, 7114863 was superior to rosiglitazone under similar experimental conditions without inducing PPAR-gamma agonist activity thus making it a very interesting scaffold. (C) 2013 Elsevier Ltd. All rights reserved.
• DE889151
  申请人：——

  公开号：——

  公开（公告）日：——
• US4171429A
  申请人：——

  公开号：US4171429A

  公开（公告）日：1979-10-16
• 2,4-Diaminopyrimidines as Antimalarials. III. 5-Aryl Derivatives
  作者：Peter B. Russell、George H. Hitchings

  DOI：10.1021/ja01152a060

  日期：1951.8