2-amino-5-butylpyrimidine-4,6-diol | 98647-80-4

• 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-butylpyrimidine-4,6-diol
• 英文别名: 2-amino-5-butyl-4,6-dihydroxypyrimidine；2-amino-5-butyl-4-hydroxy-1H-pyrimidin-6-one
• CAS: 98647-80-4
• 化学式: C₈H₁₃N₃O₂
• 分子量: 183.21
• InChiKey: KMZFXJNMMAZMIV-UHFFFAOYSA-N

物化性质

• 熔点：
  330 °C (decomp)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-5-butylpyrimidine-4,6-diol 在 盐酸 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 6.0h， 生成 5-butyl-4,6-dichloropyrimidin-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：

  盐酸胍 、 正丁基丙二酸二乙酯 在 sodium carbonate 作用下， 以 水 为溶剂， 反应 0.5h， 以72%的产率得到2-amino-5-butylpyrimidine-4,6-diol
  参考文献：
  名称：

  2-氨基嘧啶和巴比妥酸衍生物的超声辅助快速合成

  摘要：

  摘要 本文介绍了一种新颖、廉价且相对快速的方法，可从容易获得的化合物（例如盐酸胍、尿素、1,3-二烷基脲或硫脲）开始合成不同的 2-氨基嘧啶和巴比妥酸衍生物。在超声波照射下，上述底物与丙二酸二乙酯、2-烷基丙二酸二乙酯、戊烷-2,4-二酮或3-氧代丁酸乙酯在碱驱动（Na2CO3、NaOH或NaOC2H5）杂环化反应中产生相应的产物。与传统的热方法相比，这种声化学合成方案的显着优势包括简单的反应设置和后处理步骤、合理温和的条件、更短的反应时间（~30 分钟）和相对较高的产品收率。合成化合物的表征基于熔点、FT-IR、GC-MS、1H-NMR 技术，并且所获得的数据也从先前发表的研究中得到检查。图形概要

  DOI：

  10.1080/00397911.2019.1705349

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。
• 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.
• Ultrasound-assisted rapid synthesis of 2-aminopyrimidine and barbituric acid derivatives
  作者：Duygu Bayramoğlu、Gülbin Kurtay、Mustafa Güllü

  DOI：10.1080/00397911.2019.1705349

  日期：2020.3.3

  Abstract Novel, inexpensive, and relatively expeditious procedure to achieve the synthesis of different 2-aminopyrimidine and barbituric acid derivatives is presented here, starting from readily available compounds such as guanidine hydrochloride, urea, 1,3-dialkylurea, or thiourea. Under ultrasonic irradiation, base-driven (Na2CO3, NaOH, or NaOC2H5) heterocyclization reactions of the aforementioned

  摘要 本文介绍了一种新颖、廉价且相对快速的方法，可从容易获得的化合物（例如盐酸胍、尿素、1,3-二烷基脲或硫脲）开始合成不同的 2-氨基嘧啶和巴比妥酸衍生物。在超声波照射下，上述底物与丙二酸二乙酯、2-烷基丙二酸二乙酯、戊烷-2,4-二酮或3-氧代丁酸乙酯在碱驱动（Na2CO3、NaOH或NaOC2H5）杂环化反应中产生相应的产物。与传统的热方法相比，这种声化学合成方案的显着优势包括简单的反应设置和后处理步骤、合理温和的条件、更短的反应时间（~30 分钟）和相对较高的产品收率。合成化合物的表征基于熔点、FT-IR、GC-MS、1H-NMR 技术，并且所获得的数据也从先前发表的研究中得到检查。图形概要