5-benzyl-4,6-dichloropyrimidin-2-amine | 500161-38-6

• 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: 5-benzyl-4,6-dichloropyrimidin-2-amine
• 英文别名: 5-benzyl-4,6-dichloro-pyrimidin-2-ylamine；5-Benzyl-4,6-dichlor-pyrimidin-2-ylamin；2-amino-5-benzyl-4,6-dichloropyrimidine
• CAS: 500161-38-6
• 化学式: C₁₁H₉Cl₂N₃
• 分子量: 254.119
• InChiKey: USMVUFVFGUSIJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-benzyl-4,6-dichloropyrimidin-2-amine 在 乙醇 、 锌 作用下， 生成 5-benzylpyrimidin-2-amine
  参考文献：
  名称：

  Kast, Chemische Berichte, 1912, vol. 45, p. 3124

  摘要：

  DOI：
• 作为产物：
  描述：

  苄基丙二酸二乙酯 在 氨 、 sodium ethanolate 、 三氯氧磷 作用下， 生成 5-benzyl-4,6-dichloropyrimidin-2-amine
  参考文献：
  名称：

  Kast, Chemische Berichte, 1912, vol. 45, p. 3124

  摘要：

  DOI：

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。
• NOVEL PYRIMIDINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF CANCER AND FURTHER DISEASES
  申请人：Bennet Nicholas James

  公开号：US20120122867A1

  公开（公告）日：2012-05-17

  The invention concerns compounds of Formula (I): wherein L 1 , R 1 , R 2 , R 3 , R 4 and X are as defined in the description. The present invention also relates to processes for the preparation of such compounds, pharmaceutical compositions containing them and their use in the treatment of disease, for example cancer.

  本发明涉及式(I)的化合物：其中L1，R1，R2，R3，R4和X如描述中所定义。本发明还涉及制备这种化合物的方法，包含它们的制药组合物以及它们在治疗疾病（例如癌症）中的应用。
• 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。
• Novel Pyrimidine Derivatives and Their Use in the Treatment of Cancer and Further Diseases
  申请人：ASTRAZENECA AB

  公开号：US20150080396A1

  公开（公告）日：2015-03-19

  The invention concerns compounds of Formula (I): wherein L 1 , R 1 , R 2 , R 3 , R 4 and X are as defined in the description. The present invention also relates to processes for the preparation of such compounds, pharmaceutical compositions containing them and their use in the treatment of disease, for example cancer.

  本发明涉及式（I）的化合物：其中L1，R1，R2，R3，R4和X如描述中所定义。本发明还涉及制备这些化合物的工艺，含有它们的制药组合物以及它们在治疗疾病，例如癌症中的应用。
• 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.